BG60835B2 - Епинен естер, метод за получаването му и лекарства - Google Patents

Епинен естер, метод за получаването му и лекарства Download PDF

Info

Publication number: BG60835B2
Authority: BG; Bulgaria
Prior art keywords: epinine; compounds; formula; preparation; carbon atoms
Prior art date: 1976-08-05

Application number

BG098591A

Other languages

Bulgarian (bg)

English (en)

Inventor

Cesare Casagrande

Giorgio Ferrari

Original Assignee

Zambon Group S.P.A.

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.)

1976-08-05

Filing date

1994-02-25

Publication date

1996-04-30

1994-02-25 Application filed by Zambon Group S.P.A. filed Critical Zambon Group S.P.A.

1996-04-30 Publication of BG60835B2 publication Critical patent/BG60835B2/bg

Links

150000001875 compounds Chemical class 0.000 title claims abstract description 27
238000000034 method Methods 0.000 title claims abstract description 9
238000002360 preparation method Methods 0.000 title claims abstract description 4
239000003814 drug Substances 0.000 claims abstract 2
NGKZFDYBISXGGS-UHFFFAOYSA-N Epinine Natural products CNCCC1=CC=C(O)C(O)=C1 NGKZFDYBISXGGS-UHFFFAOYSA-N 0.000 claims description 19
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 11
-1 Epinine ester Chemical class 0.000 claims description 7
238000006243 chemical reaction Methods 0.000 claims description 6
230000010933 acylation Effects 0.000 claims description 4
238000005917 acylation reaction Methods 0.000 claims description 4
125000004432 carbon atom Chemical group C* 0.000 claims description 3
239000002253 acid Substances 0.000 claims description 2
125000000217 alkyl group Chemical group 0.000 claims description 2
229910052799 carbon Inorganic materials 0.000 claims description 2
GNWNHNPGRZBUAN-UHFFFAOYSA-N carbonic acid;chloromethylbenzene Chemical compound OC(O)=O.ClCC1=CC=CC=C1 GNWNHNPGRZBUAN-UHFFFAOYSA-N 0.000 claims description 2
239000012442 inert solvent Substances 0.000 claims description 2
229910052500 inorganic mineral Inorganic materials 0.000 claims description 2
239000011707 mineral Substances 0.000 claims description 2
150000007522 mineralic acids Chemical class 0.000 claims description 2
231100000252 nontoxic Toxicity 0.000 claims description 2
230000003000 nontoxic effect Effects 0.000 claims description 2
150000007524 organic acids Chemical class 0.000 claims description 2
150000003839 salts Chemical class 0.000 claims description 2
150000007933 aliphatic carboxylic acids Chemical class 0.000 claims 1
125000004429 atom Chemical group 0.000 claims 1
150000001732 carboxylic acid derivatives Chemical class 0.000 claims 1
239000000969 carrier Substances 0.000 claims 1
239000000546 pharmaceutical excipient Substances 0.000 claims 1
230000000144 pharmacologic effect Effects 0.000 abstract description 4
231100000419 toxicity Toxicity 0.000 abstract description 2
230000001988 toxicity Effects 0.000 abstract description 2
VYFYYTLLBUKUHU-UHFFFAOYSA-N dopamine Chemical compound NCCC1=CC=C(O)C(O)=C1 VYFYYTLLBUKUHU-UHFFFAOYSA-N 0.000 description 18
239000000243 solution Substances 0.000 description 12
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 10
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
229960003638 dopamine Drugs 0.000 description 9
230000037396 body weight Effects 0.000 description 6
230000008018 melting Effects 0.000 description 6
238000002844 melting Methods 0.000 description 6
239000002904 solvent Substances 0.000 description 6
150000002148 esters Chemical class 0.000 description 5
239000000203 mixture Substances 0.000 description 5
DGMOBVGABMBZSB-UHFFFAOYSA-N 2-methylpropanoyl chloride Chemical compound CC(C)C(Cl)=O DGMOBVGABMBZSB-UHFFFAOYSA-N 0.000 description 4
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
241001465754 Metazoa Species 0.000 description 4
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 4
BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 4
238000001953 recrystallisation Methods 0.000 description 4
KDYFGRWQOYBRFD-UHFFFAOYSA-N succinic acid Chemical compound OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 4
230000001225 therapeutic effect Effects 0.000 description 4
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 3
241000700159 Rattus Species 0.000 description 3
229960000583 acetic acid Drugs 0.000 description 3
230000036772 blood pressure Effects 0.000 description 3
238000001990 intravenous administration Methods 0.000 description 3
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 3
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
JVSFQJZRHXAUGT-UHFFFAOYSA-N 2,2-dimethylpropanoyl chloride Chemical compound CC(C)(C)C(Cl)=O JVSFQJZRHXAUGT-UHFFFAOYSA-N 0.000 description 2
ACICAVVXAAEHEM-UHFFFAOYSA-N 4-[2-(methylamino)ethyl]benzene-1,2-diol;hydrobromide Chemical compound Br.CNCCC1=CC=C(O)C(O)=C1 ACICAVVXAAEHEM-UHFFFAOYSA-N 0.000 description 2
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 2
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
150000001263 acyl chlorides Chemical class 0.000 description 2
150000001412 amines Chemical group 0.000 description 2
230000009286 beneficial effect Effects 0.000 description 2
230000017531 blood circulation Effects 0.000 description 2
229910021538 borax Inorganic materials 0.000 description 2
238000009903 catalytic hydrogenation reaction Methods 0.000 description 2
230000008602 contraction Effects 0.000 description 2
230000034994 death Effects 0.000 description 2
231100000517 death Toxicity 0.000 description 2
UQGFMSUEHSUPRD-UHFFFAOYSA-N disodium;3,7-dioxido-2,4,6,8,9-pentaoxa-1,3,5,7-tetraborabicyclo[3.3.1]nonane Chemical compound [Na+].[Na+].O1B([O-])OB2OB([O-])OB1O2 UQGFMSUEHSUPRD-UHFFFAOYSA-N 0.000 description 2
239000000284 extract Substances 0.000 description 2
239000007903 gelatin capsule Substances 0.000 description 2
238000001802 infusion Methods 0.000 description 2
229910052763 palladium Inorganic materials 0.000 description 2
238000007911 parenteral administration Methods 0.000 description 2
229910052697 platinum Inorganic materials 0.000 description 2
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
230000033764 rhythmic process Effects 0.000 description 2
229910000030 sodium bicarbonate Inorganic materials 0.000 description 2
235000017557 sodium bicarbonate Nutrition 0.000 description 2
239000004328 sodium tetraborate Substances 0.000 description 2
235000010339 sodium tetraborate Nutrition 0.000 description 2
238000003756 stirring Methods 0.000 description 2
239000000126 substance Substances 0.000 description 2
KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 2
239000001384 succinic acid Substances 0.000 description 2
LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 description 2
ZRNSCURSJJRPGN-UHFFFAOYSA-N 4-[2-(ethylamino)ethyl]benzene-1,2-diol Chemical compound CCNCCC1=CC=C(O)C(O)=C1 ZRNSCURSJJRPGN-UHFFFAOYSA-N 0.000 description 1
CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 1
241000282472 Canis lupus familiaris Species 0.000 description 1
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 1
102000015554 Dopamine receptor Human genes 0.000 description 1
108050004812 Dopamine receptor Proteins 0.000 description 1
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
241000699670 Mus sp. Species 0.000 description 1
OJIJMOLDUSMOIK-UHFFFAOYSA-N [4-(2-aminoethyl)-2-(2-methylpropanoyloxy)phenyl] 2-methylpropanoate Chemical compound CC(C)C(=O)OC1=CC=C(CCN)C=C1OC(=O)C(C)C OJIJMOLDUSMOIK-UHFFFAOYSA-N 0.000 description 1
230000002378 acidificating effect Effects 0.000 description 1
239000013543 active substance Substances 0.000 description 1
125000002015 acyclic group Chemical group 0.000 description 1
125000002252 acyl group Chemical group 0.000 description 1
239000000654 additive Substances 0.000 description 1
125000003277 amino group Chemical group 0.000 description 1
150000008064 anhydrides Chemical class 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
HSDAJNMJOMSNEV-UHFFFAOYSA-N benzyl chloroformate Chemical compound ClC(=O)OCC1=CC=CC=C1 HSDAJNMJOMSNEV-UHFFFAOYSA-N 0.000 description 1
102000012740 beta Adrenergic Receptors Human genes 0.000 description 1
108010079452 beta Adrenergic Receptors Proteins 0.000 description 1
230000000035 biogenic effect Effects 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
150000001735 carboxylic acids Chemical class 0.000 description 1
206010007625 cardiogenic shock Diseases 0.000 description 1
239000003054 catalyst Substances 0.000 description 1
239000003610 charcoal Substances 0.000 description 1
229940125898 compound 5 Drugs 0.000 description 1
150000004292 cyclic ethers Chemical class 0.000 description 1
239000008298 dragée Substances 0.000 description 1
230000002526 effect on cardiovascular system Effects 0.000 description 1
230000000694 effects Effects 0.000 description 1
238000001704 evaporation Methods 0.000 description 1
230000008020 evaporation Effects 0.000 description 1
230000029142 excretion Effects 0.000 description 1
238000000605 extraction Methods 0.000 description 1
230000002349 favourable effect Effects 0.000 description 1
239000000945 filler Substances 0.000 description 1
239000012362 glacial acetic acid Substances 0.000 description 1
229940093915 gynecological organic acid Drugs 0.000 description 1
230000010247 heart contraction Effects 0.000 description 1
230000000004 hemodynamic effect Effects 0.000 description 1
FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 1
229910052739 hydrogen Inorganic materials 0.000 description 1
239000001257 hydrogen Substances 0.000 description 1
QAOWNCQODCNURD-UHFFFAOYSA-M hydrogensulfate Chemical compound OS([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-M 0.000 description 1
125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
210000003734 kidney Anatomy 0.000 description 1
229910052751 metal Inorganic materials 0.000 description 1
239000002184 metal Substances 0.000 description 1
235000010755 mineral Nutrition 0.000 description 1
239000012299 nitrogen atmosphere Substances 0.000 description 1
235000005985 organic acids Nutrition 0.000 description 1
229960001412 pentobarbital Drugs 0.000 description 1
WEXRUCMBJFQVBZ-UHFFFAOYSA-N pentobarbital Chemical compound CCCC(C)C1(CC)C(=O)NC(=O)NC1=O WEXRUCMBJFQVBZ-UHFFFAOYSA-N 0.000 description 1
230000004526 pharmaceutical effect Effects 0.000 description 1
ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
230000001766 physiological effect Effects 0.000 description 1
230000002035 prolonged effect Effects 0.000 description 1
239000007787 solid Substances 0.000 description 1
238000013268 sustained release Methods 0.000 description 1
239000012730 sustained-release form Substances 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
239000003826 tablet Substances 0.000 description 1
238000002560 therapeutic procedure Methods 0.000 description 1
210000002700 urine Anatomy 0.000 description 1
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C46/00—Preparation of quinones

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)

BG098591A 1976-08-05 1994-02-25 Епинен естер, метод за получаването му и лекарства BG60835B2 (bg)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
IT26074/76A IT1074038B (it)	1976-08-05	1976-08-05	Esteri della epinina

Publications (1)

Publication Number	Publication Date
BG60835B2 true BG60835B2 (bg)	1996-04-30

Family

ID=11218576

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
BG098591A BG60835B2 (bg)	1976-08-05	1994-02-25	Епинен естер, метод за получаването му и лекарства

Country Status (17)

Country	Link
US (2)	US4218470A (nl)
JP (1)	JPS6023102B2 (nl)
BE (1)	BE857546A (nl)
BG (1)	BG60835B2 (nl)
CA (1)	CA1113117A (nl)
CH (1)	CH629178A5 (nl)
CY (1)	CY1164A (nl)
DE (1)	DE2734678C2 (nl)
ES (1)	ES461399A1 (nl)
FR (1)	FR2360558A1 (nl)
GB (1)	GB1551661A (nl)
HK (1)	HK12084A (nl)
IT (1)	IT1074038B (nl)
KE (1)	KE3238A (nl)
MX (1)	MX9203179A (nl)
MY (1)	MY8300216A (nl)
NL (1)	NL182878C (nl)

Families Citing this family (19)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
IT1190925B (it) *	1982-07-22	1988-02-24	Simes	Esteri dell'epinina
FI832128A0 (fi) *	1983-06-14	1983-06-14	Farmos Oy	Foerfarande foer framstaellning av en amin
IT1194325B (it) *	1983-07-19	1988-09-14	Simes	Composizioni farmaceutiche comprendenti epinina o un suo sale farmaceuticamente accettabile e loro uso terapeutico
US4562206A (en) *	1983-12-23	1985-12-31	Key Pharmaceuticals, Inc.	Orally effective inotropic compounds
IT1178800B (it) *	1984-12-27	1987-09-16	Simes	Composizioni farmaceutiche e loro uso come midriatici
IT1226796B (it) *	1988-07-15	1991-02-19	Simes	Composizione farmaceutica utile per il trattamento di malattie cardiovascolari.
US5246949A (en) *	1989-12-06	1993-09-21	Sansho Co., Ltd.	Preparation for endermism containing dopamine derivatives
GB9217099D0 (en) *	1992-08-12	1992-09-23	British Tech Group	Pharmaceutical compositions
WO2002056705A2 (en) *	2001-01-18	2002-07-25	Archer-Daniels-Midland Company	Method of increasing hardness of food products
US6787044B1 (en) *	2003-03-10	2004-09-07	Archimedes Technology Group, Inc.	High frequency wave heated plasma mass filter
DK1616184T4 (en) *	2003-03-27	2018-08-13	Childrens Hospital Med Ct	Method and kit for detecting early onset of renal tubular cell damage
ITMI20040146A1 (it) *	2004-01-30	2004-04-30	Acraf	Ibopamina maleato metodo per prepararlo e composizioni farmaceutiche che lo comprendono
US20050272101A1 (en) *	2004-06-07	2005-12-08	Prasad Devarajan	Method for the early detection of renal injury
EP3208616B1 (en) *	2004-12-20	2018-09-26	Antibodyshop A/S	Determination of neutrophil gelatinase-associated lipocalin (ngal) as a diagnostic marker for renal disorders
US20070037232A1 (en) *	2005-03-31	2007-02-15	Barasch Jonathan M	Detection of NGAL in chronic renal disease
US20090197280A1 (en)	2006-05-30	2009-08-06	Kristian Bangert	Methods and Devices for Rapid Assessment of Severity of Injury
US20100210031A2 (en) *	2006-08-07	2010-08-19	Antibodyshop A/S	Diagnostic Test to Exclude Significant Renal Injury
JP2010521694A (ja) *	2007-03-21	2010-06-24	バイオポルト・ダイアグノスティクス・アクティーゼルスカブ	腎傷害のための診断テスト
ES2475990T5 (es) *	2007-11-15	2017-07-06	Bioporto Diagnostics A/S	Uso diagnóstico de formas moleculares individuales de un biomarcador

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US2400038A (en) *	1944-09-07	1946-05-07	Burroughs Wellcome Co	Esters of secondary phenolic amines
US3809714A (en) *	1972-08-31	1974-05-07	Interx Research Corp	Novel ester of ((methylamino)methyl) benzyl alcohol
US3868461A (en) *	1972-11-22	1975-02-25	Interx Research Corp	Ester of 3,4-dihydroxy-alpha (isopropylamino) methyl benzyl alcohol, composition and anti-asthma use thereof
US4031242A (en) *	1975-09-11	1977-06-21	Abbott Laboratories	Diacylated derivatives of γ-glutamyl dopamine

1976
- 1976-08-05 IT IT26074/76A patent/IT1074038B/it active
1977
- 1977-07-28 CH CH935877A patent/CH629178A5/it not_active IP Right Cessation
- 1977-07-28 US US05/820,007 patent/US4218470A/en not_active Expired - Lifetime
- 1977-08-01 DE DE2734678A patent/DE2734678C2/de not_active Expired
- 1977-08-03 GB GB32584/77A patent/GB1551661A/en not_active Expired
- 1977-08-03 CY CY1164A patent/CY1164A/xx unknown
- 1977-08-04 FR FR7724075A patent/FR2360558A1/fr active Granted
- 1977-08-04 CA CA284,049A patent/CA1113117A/en not_active Expired
- 1977-08-04 NL NLAANVRAGE7708646,A patent/NL182878C/nl not_active IP Right Cessation
- 1977-08-05 BE BE179959A patent/BE857546A/xx not_active IP Right Cessation
- 1977-08-05 JP JP52093447A patent/JPS6023102B2/ja not_active Expired
- 1977-08-07 ES ES461399A patent/ES461399A1/es not_active Expired
1980
- 1980-05-20 US US06/151,632 patent/US4302471A/en not_active Expired - Lifetime
1982
- 1982-10-22 KE KE3238A patent/KE3238A/xx unknown
1983
- 1983-12-30 MY MY216/83A patent/MY8300216A/xx unknown
1984
- 1984-02-09 HK HK120/84A patent/HK12084A/xx not_active IP Right Cessation
1992
- 1992-06-23 MX MX9203179A patent/MX9203179A/es unknown
1994
- 1994-02-25 BG BG098591A patent/BG60835B2/bg unknown

Also Published As

Publication number	Publication date
CA1113117A (en)	1981-11-24
BE857546A (fr)	1977-12-01
CY1164A (en)	1983-06-10
CH629178A5 (it)	1982-04-15
ES461399A1 (es)	1978-05-16
NL7708646A (nl)	1978-02-07
DE2734678C2 (de)	1982-07-15
NL182878C (nl)	1988-06-01
KE3238A (en)	1982-12-03
JPS6023102B2 (ja)	1985-06-05
FR2360558A1 (fr)	1978-03-03
MY8300216A (en)	1983-12-31
US4302471A (en)	1981-11-24
HK12084A (en)	1984-02-17
US4218470A (en)	1980-08-19
NL182878B (nl)	1988-01-04
JPS5321130A (en)	1978-02-27
IT1074038B (it)	1985-04-17
FR2360558B1 (nl)	1980-10-03
DE2734678A1 (de)	1978-02-09
MX9203179A (es)	1992-07-01
GB1551661A (en)	1979-08-30

Publication	Publication Date	Title
BG60835B2 (bg)	1996-04-30	Епинен естер, метод за получаването му и лекарства
US3987177A (en)	1976-10-19	Vincaminic acid esters
PL117996B1 (en)	1981-09-30	Process for preparing novel,optically active phenethanoloamineslaminov
US3553258A (en)	1971-01-05	Phenylalanine compounds
JPS61155375A (ja)	1986-07-15	新規２−アミノオキサゾリン類およびその製造方法
US4367235A (en)	1983-01-04	2-Benzimidazolinone compounds and therapeutic compositions
US4683245A (en)	1987-07-28	Laevorotatory antipode of moprolol as an antihypertensive
US3982012A (en)	1976-09-21	4-Hydroxy-benzimidazole compounds and therapeutic compositions
FR2503705A1 (fr)	1982-10-15	Derives de phenethanolamine, leur preparation et leur application en therapeutique
PT100216B (pt)	1999-06-30	N-{{4,5-di-hidroxi- e 4,5,8-tri-hidroxi-9,10-di-hidro-9,10-dioxo-2-antracentil} carbonil}-aminoacidos uteis na terapia de afeccoes osteoarticulares, processo para a sua preparacao e composicoes farmaceuticas que os contem
CH643862A5 (de)	1984-06-29	Bis(4-demethoxydaunorubicin)dihydrazon-derivate und sie enthaltende pharmazeutische zubereitungen.
DE2923817C2 (de)	1981-07-09	(3-Alkylamino-2-hydroxyproposy)-furan-2-carbonsäureanilide und deren physiologisch verträgliche Säureadditionssalze und Verfahren zu deren Herstellung sowie Arzneimittel mit einem Gehalt dieser Verbindungen
US4182775A (en)	1980-01-08	Benzoic acids and process for their preparation
US4503058A (en)	1985-03-05	Therapeutically useful 3,7a-diazacyclohepta[j,k]fluorene derivatives
EP0275221B1 (fr)	1991-04-17	Nouveaux dérivés du N-(1H-indol 4-yl) benzamide ainsi que leurs sels, leur application à titre de médicaments et les compositions les renfermant
US3063899A (en)	1962-11-13	beta-hydroxybutyric acid-cyclohexylamide and a process of preparing it
DE3110376A1 (de)	1982-04-01	Benzylalkoholderivate, verfahren zu deren herstellung und arzneimittel, welche diese enthalten
EP0101633B1 (en)	1986-12-03	Pyridinecarboxylic esters of dopamine and of its n-alkyl derivatives
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