NO863944L - L-dopa-derivater, fremgangsmaate til deres fremstilling og farmasoeytisk blanding inneholdende disse derivater. - Google Patents

L-dopa-derivater, fremgangsmaate til deres fremstilling og farmasoeytisk blanding inneholdende disse derivater.

Info

Publication number: NO863944L
Authority: NO; Norway
Prior art keywords: dopa; derivative; stated; glycerol; different
Prior art date: 1985-02-04

Application number

NO863944A

Other languages

English (en)

Norwegian (no)

Other versions

NO863944D0 (no

Inventor

Pierre Dumont

Original Assignee

Univ Catholique Louvain

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.)

1985-02-04

Filing date

1986-10-03

Publication date

1986-12-01

1986-10-03 Application filed by Univ Catholique Louvain filed Critical Univ Catholique Louvain

1986-10-03 Publication of NO863944D0 publication Critical patent/NO863944D0/no

1986-12-01 Publication of NO863944L publication Critical patent/NO863944L/no

Links

WTDRDQBEARUVNC-LURJTMIESA-N L-DOPA Chemical class OC(=O)[C@@H](N)CC1=CC=C(O)C(O)=C1 WTDRDQBEARUVNC-LURJTMIESA-N 0.000 title claims description 36
238000000034 method Methods 0.000 title claims description 11
239000000203 mixture Substances 0.000 title description 3
238000002360 preparation method Methods 0.000 title description 3
WTDRDQBEARUVNC-UHFFFAOYSA-N L-Dopa Natural products OC(=O)C(N)CC1=CC=C(O)C(O)=C1 WTDRDQBEARUVNC-UHFFFAOYSA-N 0.000 claims description 25
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims description 16
125000002252 acyl group Chemical group 0.000 claims description 16
125000004432 carbon atom Chemical group C* 0.000 claims description 11
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 9
208000018737 Parkinson disease Diseases 0.000 claims description 7
230000015572 biosynthetic process Effects 0.000 claims description 6
238000003786 synthesis reaction Methods 0.000 claims description 6
239000000825 pharmaceutical preparation Substances 0.000 claims description 5
239000000725 suspension Substances 0.000 claims description 4
239000002253 acid Substances 0.000 claims description 3
239000012374 esterification agent Substances 0.000 claims description 3
150000002314 glycerols Chemical class 0.000 claims description 3
230000002093 peripheral effect Effects 0.000 claims description 3
102100038238 Aromatic-L-amino-acid decarboxylase Human genes 0.000 claims description 2
108010035075 Tyrosine decarboxylase Proteins 0.000 claims description 2
239000002671 adjuvant Substances 0.000 claims description 2
BNQDCRGUHNALGH-UHFFFAOYSA-N benserazide Chemical compound OCC(N)C(=O)NNCC1=CC=C(O)C(O)=C1O BNQDCRGUHNALGH-UHFFFAOYSA-N 0.000 claims description 2
229960000911 benserazide Drugs 0.000 claims description 2
229960004205 carbidopa Drugs 0.000 claims description 2
TZFNLOMSOLWIDK-JTQLQIEISA-N carbidopa (anhydrous) Chemical compound NN[C@@](C(O)=O)(C)CC1=CC=C(O)C(O)=C1 TZFNLOMSOLWIDK-JTQLQIEISA-N 0.000 claims description 2
239000000969 carrier Substances 0.000 claims description 2
238000012512 characterization method Methods 0.000 claims description 2
239000000839 emulsion Substances 0.000 claims description 2
235000011389 fruit/vegetable juice Nutrition 0.000 claims description 2
239000007903 gelatin capsule Substances 0.000 claims description 2
OYBLYDGMPPILJI-UHFFFAOYSA-N glycerol radical Chemical compound OC[C](O)CO OYBLYDGMPPILJI-UHFFFAOYSA-N 0.000 claims description 2
239000003112 inhibitor Substances 0.000 claims description 2
239000000543 intermediate Substances 0.000 claims description 2
238000004519 manufacturing process Methods 0.000 claims description 2
239000000546 pharmaceutical excipient Substances 0.000 claims description 2
230000008569 process Effects 0.000 claims description 2
238000000746 purification Methods 0.000 claims description 2
238000005809 transesterification reaction Methods 0.000 claims description 2
150000001875 compounds Chemical class 0.000 description 31
VYFYYTLLBUKUHU-UHFFFAOYSA-N dopamine Chemical compound NCCC1=CC=C(O)C(O)=C1 VYFYYTLLBUKUHU-UHFFFAOYSA-N 0.000 description 18
230000000694 effects Effects 0.000 description 14
229960003638 dopamine Drugs 0.000 description 9
125000005456 glyceride group Chemical group 0.000 description 7
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
239000000047 product Substances 0.000 description 6
DNXIKVLOVZVMQF-UHFFFAOYSA-N (3beta,16beta,17alpha,18beta,20alpha)-17-hydroxy-11-methoxy-18-[(3,4,5-trimethoxybenzoyl)oxy]-yohimban-16-carboxylic acid, methyl ester Natural products C1C2CN3CCC(C4=CC=C(OC)C=C4N4)=C4C3CC2C(C(=O)OC)C(O)C1OC(=O)C1=CC(OC)=C(OC)C(OC)=C1 DNXIKVLOVZVMQF-UHFFFAOYSA-N 0.000 description 5
GFAZGHREJPXDMH-UHFFFAOYSA-N 1,3-dipalmitoylglycerol Chemical compound CCCCCCCCCCCCCCCC(=O)OCC(O)COC(=O)CCCCCCCCCCCCCCC GFAZGHREJPXDMH-UHFFFAOYSA-N 0.000 description 5
RSDOPYMFZBJHRL-UHFFFAOYSA-N Oxotremorine Chemical compound O=C1CCCN1CC#CCN1CCCC1 RSDOPYMFZBJHRL-UHFFFAOYSA-N 0.000 description 5
LCQMZZCPPSWADO-UHFFFAOYSA-N Reserpilin Natural products COC(=O)C1COCC2CN3CCc4c([nH]c5cc(OC)c(OC)cc45)C3CC12 LCQMZZCPPSWADO-UHFFFAOYSA-N 0.000 description 5
QEVHRUUCFGRFIF-SFWBKIHZSA-N Reserpine Natural products O=C(OC)[C@@H]1[C@H](OC)[C@H](OC(=O)c2cc(OC)c(OC)c(OC)c2)C[C@H]2[C@@H]1C[C@H]1N(C2)CCc2c3c([nH]c12)cc(OC)cc3 QEVHRUUCFGRFIF-SFWBKIHZSA-N 0.000 description 5
BJOIZNZVOZKDIG-MDEJGZGSSA-N reserpine Chemical compound O([C@H]1[C@@H]([C@H]([C@H]2C[C@@H]3C4=C([C]5C=CC(OC)=CC5=N4)CCN3C[C@H]2C1)C(=O)OC)OC)C(=O)C1=CC(OC)=C(OC)C(OC)=C1 BJOIZNZVOZKDIG-MDEJGZGSSA-N 0.000 description 5
229960003147 reserpine Drugs 0.000 description 5
MDMGHDFNKNZPAU-UHFFFAOYSA-N roserpine Natural products C1C2CN3CCC(C4=CC=C(OC)C=C4N4)=C4C3CC2C(OC(C)=O)C(OC)C1OC(=O)C1=CC(OC)=C(OC)C(OC)=C1 MDMGHDFNKNZPAU-UHFFFAOYSA-N 0.000 description 5
241000699670 Mus sp. Species 0.000 description 4
239000008280 blood Substances 0.000 description 4
210000004369 blood Anatomy 0.000 description 4
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
206010044565 Tremor Diseases 0.000 description 3
210000004556 brain Anatomy 0.000 description 3
229910052799 carbon Inorganic materials 0.000 description 3
229940126214 compound 3 Drugs 0.000 description 3
230000001225 therapeutic effect Effects 0.000 description 3
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
206010015995 Eyelid ptosis Diseases 0.000 description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
206010007776 catatonia Diseases 0.000 description 2
238000006243 chemical reaction Methods 0.000 description 2
230000008878 coupling Effects 0.000 description 2
238000010168 coupling process Methods 0.000 description 2
238000005859 coupling reaction Methods 0.000 description 2
150000002148 esters Chemical class 0.000 description 2
239000000706 filtrate Substances 0.000 description 2
238000010579 first pass effect Methods 0.000 description 2
230000002496 gastric effect Effects 0.000 description 2
235000011187 glycerol Nutrition 0.000 description 2
230000002631 hypothermal effect Effects 0.000 description 2
230000005764 inhibitory process Effects 0.000 description 2
230000000968 intestinal effect Effects 0.000 description 2
210000004185 liver Anatomy 0.000 description 2
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 2
230000003287 optical effect Effects 0.000 description 2
230000000144 pharmacologic effect Effects 0.000 description 2
201000003004 ptosis Diseases 0.000 description 2
230000009467 reduction Effects 0.000 description 2
ADFXKUOMJKEIND-UHFFFAOYSA-N 1,3-dicyclohexylurea Chemical compound C1CCCCC1NC(=O)NC1CCCCC1 ADFXKUOMJKEIND-UHFFFAOYSA-N 0.000 description 1
RGUKYNXWOWSRET-UHFFFAOYSA-N 4-pyrrolidin-1-ylpyridine Chemical compound C1CCCN1C1=CC=NC=C1 RGUKYNXWOWSRET-UHFFFAOYSA-N 0.000 description 1
206010006100 Bradykinesia Diseases 0.000 description 1
QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 1
108010016626 Dipeptides Proteins 0.000 description 1
208000012661 Dyskinesia Diseases 0.000 description 1
229920000084 Gum arabic Polymers 0.000 description 1
208000006083 Hypokinesia Diseases 0.000 description 1
241001465754 Metazoa Species 0.000 description 1
206010052904 Musculoskeletal stiffness Diseases 0.000 description 1
206010028813 Nausea Diseases 0.000 description 1
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 1
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical group OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 1
241000978776 Senegalia senegal Species 0.000 description 1
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
241000906446 Theraps Species 0.000 description 1
239000000205 acacia gum Substances 0.000 description 1
235000010489 acacia gum Nutrition 0.000 description 1
230000009056 active transport Effects 0.000 description 1
230000004888 barrier function Effects 0.000 description 1
230000015556 catabolic process Effects 0.000 description 1
-1 catatonia and ptosis Chemical compound 0.000 description 1
210000003169 central nervous system Anatomy 0.000 description 1
230000002490 cerebral effect Effects 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
230000001713 cholinergic effect Effects 0.000 description 1
238000004587 chromatography analysis Methods 0.000 description 1
230000006378 damage Effects 0.000 description 1
238000006731 degradation reaction Methods 0.000 description 1
239000003814 drug Substances 0.000 description 1
230000002526 effect on cardiovascular system Effects 0.000 description 1
NLFBCYMMUAKCPC-KQQUZDAGSA-N ethyl (e)-3-[3-amino-2-cyano-1-[(e)-3-ethoxy-3-oxoprop-1-enyl]sulfanyl-3-oxoprop-1-enyl]sulfanylprop-2-enoate Chemical compound CCOC(=O)\C=C\SC(=C(C#N)C(N)=O)S\C=C\C(=O)OCC NLFBCYMMUAKCPC-KQQUZDAGSA-N 0.000 description 1
238000001704 evaporation Methods 0.000 description 1
230000008020 evaporation Effects 0.000 description 1
210000001035 gastrointestinal tract Anatomy 0.000 description 1
230000002440 hepatic effect Effects 0.000 description 1
ZZVJLPROFSCODQ-UHFFFAOYSA-N hexadecanoic acid;propane-1,2,3-triol Chemical compound OCC(O)CO.CCCCCCCCCCCCCCCC(O)=O.CCCCCCCCCCCCCCCC(O)=O ZZVJLPROFSCODQ-UHFFFAOYSA-N 0.000 description 1
230000006872 improvement Effects 0.000 description 1
238000010348 incorporation Methods 0.000 description 1
238000011835 investigation Methods 0.000 description 1
230000001926 lymphatic effect Effects 0.000 description 1
210000004324 lymphatic system Anatomy 0.000 description 1
229910052943 magnesium sulfate Inorganic materials 0.000 description 1
235000019341 magnesium sulphate Nutrition 0.000 description 1
238000001819 mass spectrum Methods 0.000 description 1
230000008018 melting Effects 0.000 description 1
238000002844 melting Methods 0.000 description 1
230000002503 metabolic effect Effects 0.000 description 1
239000002207 metabolite Substances 0.000 description 1
230000008693 nausea Effects 0.000 description 1
238000013421 nuclear magnetic resonance imaging Methods 0.000 description 1
238000005457 optimization Methods 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
239000011541 reaction mixture Substances 0.000 description 1
238000001953 recrystallisation Methods 0.000 description 1
239000000523 sample Substances 0.000 description 1
239000000741 silica gel Substances 0.000 description 1
229910002027 silica gel Inorganic materials 0.000 description 1
235000017557 sodium bicarbonate Nutrition 0.000 description 1
229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
238000006467 substitution reaction Methods 0.000 description 1
208000024891 symptom Diseases 0.000 description 1
230000002194 synthesizing effect Effects 0.000 description 1
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1

Classifications

- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/21—Esters, e.g. nitroglycerine, selenocyanates
- A61K31/215—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids

Landscapes

Health & Medical Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Pharmacology & Pharmacy (AREA)
Epidemiology (AREA)
Emergency Medicine (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

NO863944A 1985-02-04 1986-10-03 L-dopa-derivater, fremgangsmaate til deres fremstilling og farmasoeytisk blanding inneholdende disse derivater. NO863944L (no)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
LU85757A LU85757A1 (fr)	1985-02-04	1985-02-04	Derives nouveaux de la l-dopa,procedes pour leur preparation et compositions pharmaceutiques concernant de tels composes
PCT/BE1986/000002 WO1986004579A1 (fr)	1985-02-04	1986-01-27	Derives de l-dopa, leur preparation et compositions pharmaceutiques les contenant

Publications (2)

Publication Number	Publication Date
NO863944D0 NO863944D0 (no)	1986-10-03
NO863944L true NO863944L (no)	1986-12-01

Family

ID=19730402

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NO863944A NO863944L (no)	1985-02-04	1986-10-03	L-dopa-derivater, fremgangsmaate til deres fremstilling og farmasoeytisk blanding inneholdende disse derivater.

Country Status (7)

Country	Link
EP (1)	EP0250403A1 (fr)
JP (1)	JPS63501498A (fr)
DK (1)	DK437586A (fr)
FI (1)	FI871270A0 (fr)
LU (1)	LU85757A1 (fr)
NO (1)	NO863944L (fr)
WO (1)	WO1986004579A1 (fr)

Families Citing this family (13)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE19631189A1 (de) *	1996-08-02	1998-02-05	Max Delbrueck Centrum	Neuartige kationische Amphiphile für den liposomalen Gentransfer
WO2005121070A1 (fr)	2004-06-04	2005-12-22	Xenoport, Inc.	Promedicaments de levodopa, et compositions et leurs utilisations
JP4781352B2 (ja)	2004-06-04	2011-09-28	ゼノポート，インコーポレーテッド	レボドパプロドラッグおよびその組成物ならびにその使用
AU2006322051B2 (en)	2005-12-05	2011-09-29	Xenoport, Inc.	Levodopa prodrug mesylate, compositions thereof, and uses thereof
TW200843731A (en) *	2006-12-21	2008-11-16	Xenoport Inc	Catechol protected levodopa diester prodrugs, compositions, and methods of use
US7709527B2 (en)	2006-12-21	2010-05-04	Xenoport, Inc.	Levodopa dimethyl-substituted diester prodrugs compositions, and methods of use
EP2349973A2 (fr)	2008-10-20	2011-08-03	XenoPort, Inc.	Methodes de synthese d'un promedicament de type ester de levodopa
US8399513B2 (en)	2008-10-20	2013-03-19	Xenoport, Inc.	Levodopa prodrug mesylate hydrate
GB0904300D0 (en) *	2009-03-12	2009-04-22	Amarin Neuroscience Ltd	Essential fatty acid compounds
JP2013520521A (ja)	2009-11-09	2013-06-06	ゼノポート，インコーポレーテッド	レボドパプロドラッグの医薬組成物及び経口剤形並びに使用方法
JP2013043885A (ja) *	2011-08-26	2013-03-04	Kansai Bunri Sogo Gakuen	デヒドロアミノ酸含有グリセロール誘導体
CA3019382A1 (fr) *	2015-03-30	2016-10-06	Berlirem Gmbh	Esters de l-dopa solubles dans l'eau
EP3852722A4 (fr) *	2018-10-08	2022-08-03	Cellix Bio Private Limited	Compositions et méthodes pour le traitement de la maladie de parkinson

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
SE7605911L (sv) *	1975-06-11	1976-12-12	Merck & Co Inc	Forbettrat forfarande for framstellning av estrar av alfa-metyl-3,4-dihydroxifenylalanin
FR2365341A1 (fr) *	1976-09-28	1978-04-21	Synthelabo	Derives de l'acide l-(phenyl-3 amino-2 propionyloxy)-2 acetique
GR72800B (fr) *	1979-12-17	1983-12-05	Merck & Co Inc
US4360533A (en) *	1981-12-14	1982-11-23	Merck & Co., Inc.	Glyceryl ester of 1-methyl-2-(3,4-dihydroxyphenyl)alanine

1985
- 1985-02-04 LU LU85757A patent/LU85757A1/fr unknown
1986
- 1986-01-27 EP EP86900721A patent/EP0250403A1/fr not_active Withdrawn
- 1986-01-27 JP JP61500751A patent/JPS63501498A/ja active Pending
- 1986-01-27 WO PCT/BE1986/000002 patent/WO1986004579A1/fr not_active Ceased
- 1986-09-12 DK DK437586A patent/DK437586A/da not_active Application Discontinuation
- 1986-10-03 NO NO863944A patent/NO863944L/no unknown
1987
- 1987-03-23 FI FI871270A patent/FI871270A0/fi not_active IP Right Cessation

Also Published As

Publication number	Publication date
JPS63501498A (ja)	1988-06-09
EP0250403A1 (fr)	1988-01-07
DK437586D0 (da)	1986-09-12
NO863944D0 (no)	1986-10-03
FI871270A7 (fi)	1987-03-23
WO1986004579A1 (fr)	1986-08-14
FI871270A0 (fi)	1987-03-23
LU85757A1 (fr)	1986-09-02
DK437586A (da)	1986-09-12

Publication	Publication Date	Title
US4086338A (en)	1978-04-25	N-carboxyalkanoyl derivatives of azetidine-2-carboxylic acid
JP2529172B2 (ja)	1996-08-28	アミノ酸から誘導される新規な光学異性体と、その製造方法と、その医薬への応用
EP0049658B1 (fr)	1984-06-13	Iminodiacides substitués, leur préparation et compositions pharmaceutiques les contenant
KR20210043617A (ko)	2021-04-21	케토아미드계 화합물 및 이의 제조 방법, 약학 조성물과 용도
JPS6121226B2 (fr)	1986-05-26
NO863944L (no)	1986-12-01	L-dopa-derivater, fremgangsmaate til deres fremstilling og farmasoeytisk blanding inneholdende disse derivater.
JPH0587504B2 (fr)	1993-12-16
US4329495A (en)	1982-05-11	Enkephalinase enzyme inhibiting compounds
US4154937A (en)	1979-05-15	Hydroxycarbamoylalkylacylpipecolic acid compounds
JPH0296556A (ja)	1990-04-09	γ―グルタミル―Ｌ―ドパ誘導体、その製法ならびに該化合物を主成分として含むドパミン代用薬
US4724238A (en)	1988-02-09	Method of treating inflammatory diseases with labdan derivatives
AU613890B2 (en)	1991-08-15	4-thiazolidinecarboxylic acid derivative, its preparation and pharmaceutical compositions containing it
SU1327787A3 (ru)	1987-07-30	Способ получени цис,эндо-2-азабицикло-/3,3,0/-октан-3-карбоновых кислот или их кислотно-аддитивных солей
US3843796A (en)	1974-10-22	Antihypertensive agents
US5747521A (en)	1998-05-05	N-cinnamoyl-2-methyl-5-methoxy-3-indoleacetic acid ester, and pharmaceutical preparation containing the same
JPH02124884A (ja)	1990-05-14	Ｎ―置換アミド誘導体
JP5903166B2 (ja)	2016-04-13	ブチルフタリドの誘導体、並びにその製造法及び使用
US5288898A (en)	1994-02-22	N-methylphenylserine alkyl ester derivatives and uses thereof
US5451606A (en)	1995-09-19	Anthraquinone compounds useful to treat osteoarticular conditions, pharmaceutical compositions and method of treatment
EP0894794A1 (fr)	1999-02-03	Isomères optiques du clopérastine
US4695654A (en)	1987-09-22	Gem-dihalo-1,8-diamino-4-aza-octanes
NO771937L (no)	1977-12-06	Benzyl og beslektede estere av 6,11-dihydrodibenz(b,e)oksepin-eddiksyrer
US4914240A (en)	1990-04-03	Gem-dihalo-1, 8-diamino-4-aza-octanes
EP0218440A2 (fr)	1987-04-15	Dérivés d'esters alkylés de la N-méthylphénylsérine et leurs utilisations
EP0085283A1 (fr)	1983-08-10	Dérivés de pyroglutamyltryptophane, procédé pour leur préparation et leurs applications thérapeutiques