CA1113958A - N-.epsilon.-TRIMETHYL-L-LYSINE SALTS - Google Patents

N-.epsilon.-TRIMETHYL-L-LYSINE SALTS

Info

Publication number: CA1113958A
Authority: CA; Canada
Prior art keywords: trimethyl; lysine; epsilon; acid; aqueous solution
Prior art date: 1977-10-13
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.): Expired

Application number

CA313,224A

Other languages

English (en)

French (fr)

Inventor

Karoly Lapis

Bela Szende

Andras Jeney

Zsuzsa Suba

Laszlo Kovacs

Erno Tyihak

Lajos Kisfaludy

Jajos Kovacs

Gyorgy Dobo

Bela Szarvady

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Richter Gedeon Vegyeszeti Gyar Nyrt

Original Assignee

Richter Gedeon Vegyeszeti Gyar RT

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.)

1977-10-13

Filing date

1978-10-12

Publication date

1981-12-08

1978-10-12 Application filed by Richter Gedeon Vegyeszeti Gyar RT filed Critical Richter Gedeon Vegyeszeti Gyar RT

1981-12-08 Application granted granted Critical

1981-12-08 Publication of CA1113958A publication Critical patent/CA1113958A/en

Status Expired legal-status Critical Current

Links

MXNRLFUSFKVQSK-QMMMGPOBSA-O N(6),N(6),N(6)-trimethyl-L-lysine Chemical class C[N+](C)(C)CCCC[C@H]([NH3+])C([O-])=O MXNRLFUSFKVQSK-QMMMGPOBSA-O 0.000 title claims description 16
WHUUTDBJXJRKMK-VKHMYHEASA-N L-glutamic acid Chemical compound OC(=O)[C@@H](N)CCC(O)=O WHUUTDBJXJRKMK-VKHMYHEASA-N 0.000 claims abstract description 23
150000003839 salts Chemical class 0.000 claims abstract description 17
VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 claims abstract description 15
238000000034 method Methods 0.000 claims abstract description 12
CKLJMWTZIZZHCS-REOHCLBHSA-N L-aspartic acid Chemical compound OC(=O)[C@@H](N)CC(O)=O CKLJMWTZIZZHCS-REOHCLBHSA-N 0.000 claims abstract description 9
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 claims abstract description 8
235000003704 aspartic acid Nutrition 0.000 claims abstract description 7
OQFSQFPPLPISGP-UHFFFAOYSA-N beta-carboxyaspartic acid Natural products OC(=O)C(N)C(C(O)=O)C(O)=O OQFSQFPPLPISGP-UHFFFAOYSA-N 0.000 claims abstract description 7
239000001530 fumaric acid Substances 0.000 claims abstract description 7
229960002989 glutamic acid Drugs 0.000 claims abstract description 6
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 10
239000007864 aqueous solution Substances 0.000 claims description 8
150000001875 compounds Chemical class 0.000 claims description 7
239000002253 acid Substances 0.000 claims description 6
239000000126 substance Substances 0.000 claims description 6
CKLJMWTZIZZHCS-UHFFFAOYSA-N Aspartic acid Chemical compound OC(=O)C(N)CC(O)=O CKLJMWTZIZZHCS-UHFFFAOYSA-N 0.000 claims description 2
238000004519 manufacturing process Methods 0.000 claims 4
QISOBCMNUJQOJU-UHFFFAOYSA-N 4-bromo-1h-pyrazole-5-carboxylic acid Chemical compound OC(=O)C=1NN=CC=1Br QISOBCMNUJQOJU-UHFFFAOYSA-N 0.000 claims 1
WHUUTDBJXJRKMK-UHFFFAOYSA-N Glutamic acid Natural products OC(=O)C(N)CCC(O)=O WHUUTDBJXJRKMK-UHFFFAOYSA-N 0.000 claims 1
229940009098 aspartate Drugs 0.000 claims 1
235000013922 glutamic acid Nutrition 0.000 claims 1
239000004220 glutamic acid Substances 0.000 claims 1
ZDXPYRJPNDTMRX-UHFFFAOYSA-M glutaminate Chemical class [O-]C(=O)C(N)CCC(N)=O ZDXPYRJPNDTMRX-UHFFFAOYSA-M 0.000 claims 1
239000000203 mixture Substances 0.000 abstract description 5
238000002360 preparation method Methods 0.000 abstract description 3
230000000144 pharmacologic effect Effects 0.000 abstract description 2
239000000243 solution Substances 0.000 description 10
210000004881 tumor cell Anatomy 0.000 description 9
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
241000699670 Mus sp. Species 0.000 description 8
241001465754 Metazoa Species 0.000 description 7
238000010348 incorporation Methods 0.000 description 7
230000001965 increasing effect Effects 0.000 description 7
238000012360 testing method Methods 0.000 description 7
210000004027 cell Anatomy 0.000 description 6
239000012153 distilled water Substances 0.000 description 6
230000000694 effects Effects 0.000 description 6
229960005261 aspartic acid Drugs 0.000 description 5
238000004820 blood count Methods 0.000 description 4
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
238000004458 analytical method Methods 0.000 description 3
208000007502 anemia Diseases 0.000 description 3
239000003610 charcoal Substances 0.000 description 3
KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
239000000824 cytostatic agent Substances 0.000 description 3
230000007423 decrease Effects 0.000 description 3
238000001704 evaporation Methods 0.000 description 3
230000008020 evaporation Effects 0.000 description 3
210000003405 ileum Anatomy 0.000 description 3
238000002844 melting Methods 0.000 description 3
230000008018 melting Effects 0.000 description 3
238000003756 stirring Methods 0.000 description 3
238000002054 transplantation Methods 0.000 description 3
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
206010003445 Ascites Diseases 0.000 description 2
238000011765 DBA/2 mouse Methods 0.000 description 2
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
KDXKERNSBIXSRK-YFKPBYRVSA-N L-lysine Chemical class NCCCC[C@H](N)C(O)=O KDXKERNSBIXSRK-YFKPBYRVSA-N 0.000 description 2
HLFSDGLLUJUHTE-SNVBAGLBSA-N Levamisole Chemical compound C1([C@H]2CN3CCSC3=N2)=CC=CC=C1 HLFSDGLLUJUHTE-SNVBAGLBSA-N 0.000 description 2
239000004472 Lysine Substances 0.000 description 2
241001494479 Pecora Species 0.000 description 2
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
230000024932 T cell mediated immunity Effects 0.000 description 2
IQFYYKKMVGJFEH-XLPZGREQSA-N Thymidine Chemical compound O=C1NC(=O)C(C)=CN1[C@@H]1O[C@H](CO)[C@@H](O)C1 IQFYYKKMVGJFEH-XLPZGREQSA-N 0.000 description 2
229940024606 amino acid Drugs 0.000 description 2
235000001014 amino acid Nutrition 0.000 description 2
150000001413 amino acids Chemical class 0.000 description 2
239000000427 antigen Substances 0.000 description 2
102000036639 antigens Human genes 0.000 description 2
108091007433 antigens Proteins 0.000 description 2
230000037396 body weight Effects 0.000 description 2
238000006243 chemical reaction Methods 0.000 description 2
230000001085 cytostatic effect Effects 0.000 description 2
201000010099 disease Diseases 0.000 description 2
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 2
210000003743 erythrocyte Anatomy 0.000 description 2
229960002598 fumaric acid Drugs 0.000 description 2
230000000266 injurious effect Effects 0.000 description 2
229960001614 levamisole Drugs 0.000 description 2
210000004698 lymphocyte Anatomy 0.000 description 2
QBQQKHZEHKZMJF-NXUSYKNTSA-N mioe Chemical compound C=1([C@@H]2OC(=O)C[C@@H]3[C@@]2(C)CC[C@H]2C3=C[C@@H]3[C@@H](OC(=O)C(C)C)C(C)(C)[C@@H]([C@@]2(C)C3=O)CC(=O)OC)C=COC=1 QBQQKHZEHKZMJF-NXUSYKNTSA-N 0.000 description 2
VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 2
210000000952 spleen Anatomy 0.000 description 2
239000007858 starting material Substances 0.000 description 2
210000001541 thymus gland Anatomy 0.000 description 2
NGKOCETVOBCCII-UHFFFAOYSA-N 2,3,5,6-tetrahydroimidazo[2,1-b][1,3]thiazole Chemical compound C1CN=C2SCCN21 NGKOCETVOBCCII-UHFFFAOYSA-N 0.000 description 1
SVTBMSDMJJWYQN-UHFFFAOYSA-N 2-methylpentane-2,4-diol Chemical compound CC(O)CC(C)(C)O SVTBMSDMJJWYQN-UHFFFAOYSA-N 0.000 description 1
241000186361 Actinobacteria <class> Species 0.000 description 1
DWRXFEITVBNRMK-UHFFFAOYSA-N Beta-D-1-Arabinofuranosylthymine Natural products O=C1NC(=O)C(C)=CN1C1C(O)C(O)C(CO)O1 DWRXFEITVBNRMK-UHFFFAOYSA-N 0.000 description 1
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
KRKNYBCHXYNGOX-UHFFFAOYSA-K Citrate Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 description 1
241000588724 Escherichia coli Species 0.000 description 1
CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 1
CKLJMWTZIZZHCS-UWTATZPHSA-N L-Aspartic acid Natural products OC(=O)[C@H](N)CC(O)=O CKLJMWTZIZZHCS-UWTATZPHSA-N 0.000 description 1
KDXKERNSBIXSRK-UHFFFAOYSA-N Lysine Natural products NCCCCC(N)C(O)=O KDXKERNSBIXSRK-UHFFFAOYSA-N 0.000 description 1
241000124008 Mammalia Species 0.000 description 1
206010028980 Neoplasm Diseases 0.000 description 1
PVNIIMVLHYAWGP-UHFFFAOYSA-N Niacin Chemical compound OC(=O)C1=CC=CN=C1 PVNIIMVLHYAWGP-UHFFFAOYSA-N 0.000 description 1
QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
229960000583 acetic acid Drugs 0.000 description 1
235000009697 arginine Nutrition 0.000 description 1
150000001484 arginines Chemical class 0.000 description 1
IQFYYKKMVGJFEH-UHFFFAOYSA-N beta-L-thymidine Natural products O=C1NC(=O)C(C)=CN1C1OC(CO)C(O)C1 IQFYYKKMVGJFEH-UHFFFAOYSA-N 0.000 description 1
210000004369 blood Anatomy 0.000 description 1
239000008280 blood Substances 0.000 description 1
210000000601 blood cell Anatomy 0.000 description 1
210000001185 bone marrow Anatomy 0.000 description 1
210000002798 bone marrow cell Anatomy 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
238000002512 chemotherapy Methods 0.000 description 1
229940000425 combination drug Drugs 0.000 description 1
239000013078 crystal Substances 0.000 description 1
238000000354 decomposition reaction Methods 0.000 description 1
239000002552 dosage form Substances 0.000 description 1
239000002158 endotoxin Substances 0.000 description 1
238000000605 extraction Methods 0.000 description 1
239000000706 filtrate Substances 0.000 description 1
239000012362 glacial acetic acid Substances 0.000 description 1
230000028996 humoral immune response Effects 0.000 description 1
230000004727 humoral immunity Effects 0.000 description 1
238000000338 in vitro Methods 0.000 description 1
238000001727 in vivo Methods 0.000 description 1
238000011835 investigation Methods 0.000 description 1
239000007788 liquid Substances 0.000 description 1
210000004400 mucous membrane Anatomy 0.000 description 1
XXEWFEBMSGLYBY-SSDOTTSWSA-N n-dimethyl-lysine Chemical compound CN(C)CCCC[C@@H](N)C(O)=O XXEWFEBMSGLYBY-SSDOTTSWSA-N 0.000 description 1
239000005445 natural material Substances 0.000 description 1
235000001968 nicotinic acid Nutrition 0.000 description 1
239000011664 nicotinic acid Substances 0.000 description 1
FEMOMIGRRWSMCU-UHFFFAOYSA-N ninhydrin Chemical compound C1=CC=C2C(=O)C(O)(O)C(=O)C2=C1 FEMOMIGRRWSMCU-UHFFFAOYSA-N 0.000 description 1
210000005259 peripheral blood Anatomy 0.000 description 1
239000011886 peripheral blood Substances 0.000 description 1
239000008194 pharmaceutical composition Substances 0.000 description 1
210000002826 placenta Anatomy 0.000 description 1
239000013641 positive control Substances 0.000 description 1
239000000047 product Substances 0.000 description 1
230000002062 proliferating effect Effects 0.000 description 1
238000001953 recrystallisation Methods 0.000 description 1
230000004044 response Effects 0.000 description 1
210000002966 serum Anatomy 0.000 description 1
238000007493 shaping process Methods 0.000 description 1
238000010583 slow cooling Methods 0.000 description 1
239000011780 sodium chloride Substances 0.000 description 1
239000007787 solid Substances 0.000 description 1
239000011877 solvent mixture Substances 0.000 description 1
241000894007 species Species 0.000 description 1
229910021653 sulphate ion Inorganic materials 0.000 description 1
230000003407 synthetizing effect Effects 0.000 description 1
DLYUQMMRRRQYAE-UHFFFAOYSA-N tetraphosphorus decaoxide Chemical compound O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 description 1
238000004809 thin layer chromatography Methods 0.000 description 1
229940104230 thymidine Drugs 0.000 description 1
230000001131 transforming effect Effects 0.000 description 1
238000005303 weighing Methods 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C57/00—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms
- C07C57/02—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms with only carbon-to-carbon double bonds as unsaturation
- C07C57/13—Dicarboxylic acids
- C07C57/15—Fumaric acid
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/02—Immunomodulators
- A61P37/04—Immunostimulants
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
- A61P7/06—Antianaemics

Landscapes

Health & Medical Sciences (AREA)
Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Pharmacology & Pharmacy (AREA)
Animal Behavior & Ethology (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Veterinary Medicine (AREA)
Immunology (AREA)
Life Sciences & Earth Sciences (AREA)
Public Health (AREA)
General Health & Medical Sciences (AREA)
Bioinformatics & Cheminformatics (AREA)
Engineering & Computer Science (AREA)
Diabetes (AREA)
Hematology (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

CA313,224A 1977-10-13 1978-10-12 N-.epsilon.-TRIMETHYL-L-LYSINE SALTS Expired CA1113958A (en)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
HU77RI648A HU174503B (hu)	1977-10-13	1977-10-13	Sposob poluchenija novykh solejj n-e-trimetil-l-lizina
HURI-648		1977-10-13

Publications (1)

Publication Number	Publication Date
CA1113958A true CA1113958A (en)	1981-12-08

Family

ID=11001044

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA313,224A Expired CA1113958A (en)	1977-10-13	1978-10-12	N-.epsilon.-TRIMETHYL-L-LYSINE SALTS

Country Status (14)

Country	Link
JP (1)	JPS5858340B2 (da)
AT (1)	AT360501B (da)
AU (1)	AU520254B2 (da)
BE (1)	BE871196A (da)
CA (1)	CA1113958A (da)
CH (1)	CH638175A5 (da)
DE (1)	DE2844501A1 (da)
DK (1)	DK148355C (da)
FR (1)	FR2405925A1 (da)
GB (1)	GB2006207B (da)
HU (1)	HU174503B (da)
IL (1)	IL55645A (da)
NL (1)	NL7810331A (da)
YU (1)	YU40987B (da)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US7932287B2 (en) *	2004-08-12	2011-04-26	Chemgenes Corporation	Therapeutic compositions and uses

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
GB1093937A (en) *	1963-11-22	1967-12-06	Takeda Chemical Industries Ltd	Betaines of lysine

1977
- 1977-10-13 HU HU77RI648A patent/HU174503B/hu unknown
1978
- 1978-09-26 IL IL55645A patent/IL55645A/xx unknown
- 1978-10-04 AT AT714578A patent/AT360501B/de not_active IP Right Cessation
- 1978-10-11 AU AU40595/78A patent/AU520254B2/en not_active Expired
- 1978-10-11 FR FR7829002A patent/FR2405925A1/fr active Granted
- 1978-10-12 CA CA313,224A patent/CA1113958A/en not_active Expired
- 1978-10-12 BE BE191064A patent/BE871196A/xx not_active IP Right Cessation
- 1978-10-12 DE DE19782844501 patent/DE2844501A1/de not_active Withdrawn
- 1978-10-12 GB GB7840314A patent/GB2006207B/en not_active Expired
- 1978-10-12 CH CH1060878A patent/CH638175A5/de not_active IP Right Cessation
- 1978-10-12 YU YU2393/78A patent/YU40987B/xx unknown
- 1978-10-12 DK DK455378A patent/DK148355C/da not_active IP Right Cessation
- 1978-10-13 JP JP53126033A patent/JPS5858340B2/ja not_active Expired
- 1978-10-13 NL NL7810331A patent/NL7810331A/xx not_active Application Discontinuation

Also Published As

Publication number	Publication date
DK148355B (da)	1985-06-17
AU4059578A (en)	1980-04-17
ATA714578A (de)	1980-06-15
JPS5463014A (en)	1979-05-21
DK148355C (da)	1986-02-10
FR2405925A1 (fr)	1979-05-11
DE2844501A1 (de)	1979-04-19
BE871196A (fr)	1979-04-12
GB2006207A (en)	1979-05-02
FR2405925B1 (da)	1983-11-18
IL55645A (en)	1981-11-30
JPS5858340B2 (ja)	1983-12-24
HU174503B (hu)	1980-01-28
AT360501B (de)	1981-01-12
AU520254B2 (en)	1982-01-21
NL7810331A (nl)	1979-04-18
IL55645A0 (en)	1978-12-17
CH638175A5 (de)	1983-09-15
GB2006207B (en)	1982-03-03
DK455378A (da)	1979-04-14
YU40987B (en)	1986-10-31
YU239378A (en)	1983-04-30

Legal Events

Date	Code	Title	Description
1998-12-08	MKEX	Expiry

Publication	Publication Date	Title
US5739169A (en)	1998-04-14	Aromatic compounds for inhibiting immune response
SU1528317A3 (ru)	1989-12-07	Способ получени 3-(4-замещенный фенил)-5-ациламидометилоксазолидинонов-2
US5480884A (en)	1996-01-02	Compounds having a guanidine structure
CA1284329C (en)	1991-05-21	[(2,3,9,9a-tetrahydro-3-oxo-9a-substituted-1h-fluoren-7-yl) oxy] ethanimidamides and [(2,3,9,9a-tetrahydro-3-oxo-9a- substituted-1h-fluoren-7-yl) oxy]-ethanimidic acid hydrazides,their derivatives and their salts
Plapinger et al.	1953	A Nitrogen-to-Oxygen Phosphoryl Migration: Preparation of dl-Serinephosphoric and Threoninephosphoric Acid
CA1113958A (en)	1981-12-08	N-.epsilon.-TRIMETHYL-L-LYSINE SALTS
SU1616520A3 (ru)	1990-12-23	Способ получени производных пристинамицина
US3920630A (en)	1975-11-18	2,2{40 -Anhydro-ara-cytidine compounds and process of preparation
Rabinowitz et al.	1953	Some Pyrimidine Derivatives1
CA1240326A (en)	1988-08-09	2-(.omega.-ALKYLAMINOALKYL)-AND 2-(.omega.-DIALKYLAMINOALKYL)- 3-(4-X-BENZYLIDEN)-PHTALIMIDINES
RU2084449C1 (ru)	1997-07-20	1-бензил-2-оксотриптамин гидрохлорид и его производные, обладающие гепатозащитной активностью
CA2673065C (en)	2015-10-20	Novel aminoguanidines as melanocortin receptor ligands
US4165312A (en)	1979-08-21	Phosphorylated nonapeptides, processes for the preparation thereof and pharmaceutical compositions containing them
JPH04502149A (ja)	1992-04-16	２―アミノカルボン酸およびそれらの誘導体、それらの調製方法およびそれらの医薬としての使用
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Hearn et al.	1957	Stereoisomerism of N, N'-Oxalylbis-(alanine) Derivatives1
US3377359A (en)	1968-04-09	Amino derivatives, comprising heterocycles, their salts, and process for preparation
SU1053474A1 (ru)	1985-08-07	3-Фтор-2,3-дидезоксигуанозин,про вл ющий цитостатическую активность
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EP0154173B1 (en)	1992-01-08	Pteridine derivatives, an anticancer composition containing same and a process for the production of said derivatives
SU1705292A1 (ru)	1992-01-15	N-(4-хлорфенил)-2-[(бензо-2,1,3-тиадиазол-4-сульфонил)амино]-5-хлорбензамид, обладающий антигельминтной активностью
SU1456016A3 (ru)	1989-01-30	Способ получени имидазолсодержащих соединений или их кислотно-аддитивных солей