JPS63501498A - Ｌ‐ドーパの新規誘導体、その製法とそれを含有する医薬組成物 - Google Patents

Ｌ‐ドーパの新規誘導体、その製法とそれを含有する医薬組成物

Info

Publication number: JPS63501498A
Authority: JP; Japan
Prior art keywords: dopa; glycerin; acyl; formula; carbon atoms
Prior art date: 1985-02-04
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.): Pending

Application number

JP61500751A

Other languages

English (en)

Japanese (ja)

Inventor

ドゥモント・ピエール

Original Assignee

ユニバシテ・カソリック・デ・ロ−ベイン

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

1986-01-27

Publication date

1988-06-09

1986-01-27 Application filed by ユニバシテ・カソリック・デ・ロ−ベイン filed Critical ユニバシテ・カソリック・デ・ロ−ベイン

1988-06-09 Publication of JPS63501498A publication Critical patent/JPS63501498A/ja

Status Pending legal-status Critical Current

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 30
239000008194 pharmaceutical composition Substances 0.000 title claims description 6
238000004519 manufacturing process Methods 0.000 title claims description 5
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims description 23
125000002252 acyl group Chemical group 0.000 claims description 17
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 13
238000000034 method Methods 0.000 claims description 12
235000011187 glycerol Nutrition 0.000 claims description 11
125000004432 carbon atom Chemical group C* 0.000 claims description 9
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 8
208000018737 Parkinson disease Diseases 0.000 claims description 6
239000004480 active ingredient Substances 0.000 claims description 4
239000003795 chemical substances by application Substances 0.000 claims description 4
239000000126 substance Substances 0.000 claims description 4
239000002253 acid Substances 0.000 claims description 3
230000015572 biosynthetic process Effects 0.000 claims description 3
150000002148 esters Chemical class 0.000 claims description 3
239000000725 suspension Substances 0.000 claims description 3
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
239000000839 emulsion Substances 0.000 claims description 2
239000007903 gelatin capsule Substances 0.000 claims description 2
150000002314 glycerols Chemical class 0.000 claims description 2
210000000578 peripheral nerve Anatomy 0.000 claims description 2
238000003786 synthesis reaction Methods 0.000 claims description 2
239000006188 syrup Substances 0.000 claims description 2
235000020357 syrup Nutrition 0.000 claims description 2
238000005809 transesterification reaction Methods 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 1
229960000911 benserazide Drugs 0.000 claims 1
238000012512 characterization method Methods 0.000 claims 1
239000003112 inhibitor Substances 0.000 claims 1
239000000825 pharmaceutical preparation Substances 0.000 claims 1
238000000746 purification Methods 0.000 claims 1
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 14
230000000694 effects Effects 0.000 description 14
238000012360 testing method Methods 0.000 description 11
229960003638 dopamine Drugs 0.000 description 7
RSDOPYMFZBJHRL-UHFFFAOYSA-N Oxotremorine Chemical compound O=C1CCCN1CC#CCN1CCCC1 RSDOPYMFZBJHRL-UHFFFAOYSA-N 0.000 description 4
229910052799 carbon Inorganic materials 0.000 description 4
239000000047 product Substances 0.000 description 4
239000000243 solution Substances 0.000 description 4
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
210000004556 brain Anatomy 0.000 description 3
239000003814 drug Substances 0.000 description 3
230000002496 gastric effect Effects 0.000 description 3
125000005456 glyceride group Chemical group 0.000 description 3
230000000144 pharmacologic effect Effects 0.000 description 3
208000024891 symptom Diseases 0.000 description 3
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 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
241000699670 Mus sp. Species 0.000 description 2
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
206010007776 catatonia Diseases 0.000 description 2
201000010099 disease Diseases 0.000 description 2
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 2
229940079593 drug Drugs 0.000 description 2
238000011156 evaluation Methods 0.000 description 2
230000029142 excretion Effects 0.000 description 2
230000002631 hypothermal effect Effects 0.000 description 2
230000000968 intestinal effect Effects 0.000 description 2
210000004185 liver Anatomy 0.000 description 2
210000002751 lymph Anatomy 0.000 description 2
238000005259 measurement Methods 0.000 description 2
239000000203 mixture Substances 0.000 description 2
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 2
230000003285 pharmacodynamic effect Effects 0.000 description 2
201000003004 ptosis Diseases 0.000 description 2
230000009103 reabsorption Effects 0.000 description 2
230000001629 suppression Effects 0.000 description 2
230000001225 therapeutic effect Effects 0.000 description 2
102100038238 Aromatic-L-amino-acid decarboxylase Human genes 0.000 description 1
206010006100 Bradykinesia Diseases 0.000 description 1
YDNKGFDKKRUKPY-JHOUSYSJSA-N C16 ceramide Natural products CCCCCCCCCCCCCCCC(=O)N[C@@H](CO)[C@H](O)C=CCCCCCCCCCCCCC YDNKGFDKKRUKPY-JHOUSYSJSA-N 0.000 description 1
108010016626 Dipeptides Proteins 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
241000699666 Mus <mouse, genus> Species 0.000 description 1
CRJGESKKUOMBCT-VQTJNVASSA-N N-acetylsphinganine Chemical compound CCCCCCCCCCCCCCC[C@@H](O)[C@H](CO)NC(C)=O CRJGESKKUOMBCT-VQTJNVASSA-N 0.000 description 1
238000011785 NMRI mouse Methods 0.000 description 1
206010028813 Nausea Diseases 0.000 description 1
241000287462 Phalacrocorax carbo Species 0.000 description 1
241000978776 Senegalia senegal Species 0.000 description 1
206010044565 Tremor Diseases 0.000 description 1
108010035075 Tyrosine decarboxylase Proteins 0.000 description 1
HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
235000010489 acacia gum Nutrition 0.000 description 1
239000000205 acacia gum Substances 0.000 description 1
239000013543 active substance Substances 0.000 description 1
239000002671 adjuvant Substances 0.000 description 1
239000008280 blood Substances 0.000 description 1
210000004369 blood Anatomy 0.000 description 1
230000008499 blood brain barrier function Effects 0.000 description 1
230000036765 blood level Effects 0.000 description 1
210000001218 blood-brain barrier Anatomy 0.000 description 1
150000001721 carbon Chemical group 0.000 description 1
230000005800 cardiovascular problem Effects 0.000 description 1
239000000969 carrier Substances 0.000 description 1
239000003054 catalyst Substances 0.000 description 1
238000004517 catalytic hydrocracking Methods 0.000 description 1
210000003169 central nervous system Anatomy 0.000 description 1
229940106189 ceramide Drugs 0.000 description 1
ZVEQCJWYRWKARO-UHFFFAOYSA-N ceramide Natural products CCCCCCCCCCCCCCC(O)C(=O)NC(CO)C(O)C=CCCC=C(C)CCCCCCCCC ZVEQCJWYRWKARO-UHFFFAOYSA-N 0.000 description 1
238000006243 chemical reaction Methods 0.000 description 1
239000004020 conductor Substances 0.000 description 1
235000009508 confectionery Nutrition 0.000 description 1
238000000354 decomposition reaction Methods 0.000 description 1
125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
238000009826 distribution Methods 0.000 description 1
238000000921 elemental analysis Methods 0.000 description 1
238000010828 elution Methods 0.000 description 1
238000005516 engineering process Methods 0.000 description 1
238000002474 experimental method Methods 0.000 description 1
239000000706 filtrate Substances 0.000 description 1
235000013305 food Nutrition 0.000 description 1
238000009472 formulation Methods 0.000 description 1
238000003304 gavage Methods 0.000 description 1
-1 glycerin ester Chemical class 0.000 description 1
JUVJQIPDVWOVNP-UHFFFAOYSA-N hexylurea Chemical compound CCCCCCNC(N)=O JUVJQIPDVWOVNP-UHFFFAOYSA-N 0.000 description 1
238000010348 incorporation Methods 0.000 description 1
230000005764 inhibitory process Effects 0.000 description 1
238000002347 injection Methods 0.000 description 1
239000007924 injection Substances 0.000 description 1
239000000543 intermediate Substances 0.000 description 1
210000000936 intestine Anatomy 0.000 description 1
150000002500 ions Chemical class 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
238000003760 magnetic stirring Methods 0.000 description 1
238000001819 mass spectrum Methods 0.000 description 1
238000002844 melting Methods 0.000 description 1
230000008018 melting Effects 0.000 description 1
239000002207 metabolite Substances 0.000 description 1
XONPDZSGENTBNJ-UHFFFAOYSA-N molecular hydrogen;sodium Chemical compound [Na].[H][H] XONPDZSGENTBNJ-UHFFFAOYSA-N 0.000 description 1
JKRHDMPWBFBQDZ-UHFFFAOYSA-N n'-hexylmethanediimine Chemical compound CCCCCCN=C=N JKRHDMPWBFBQDZ-UHFFFAOYSA-N 0.000 description 1
230000008693 nausea Effects 0.000 description 1
VVGIYYKRAMHVLU-UHFFFAOYSA-N newbouldiamide Natural products CCCCCCCCCCCCCCCCCCCC(O)C(O)C(O)C(CO)NC(=O)CCCCCCCCCCCCCCCCC VVGIYYKRAMHVLU-UHFFFAOYSA-N 0.000 description 1
238000010899 nucleation Methods 0.000 description 1
230000003287 optical effect Effects 0.000 description 1
238000005457 optimization Methods 0.000 description 1
229910052763 palladium Inorganic materials 0.000 description 1
230000002093 peripheral effect Effects 0.000 description 1
239000000546 pharmaceutical excipient Substances 0.000 description 1
125000002467 phosphate group Chemical group [H]OP(=O)(O[H])O[*] 0.000 description 1
150000003017 phosphorus Chemical class 0.000 description 1
230000008092 positive effect Effects 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
238000002360 preparation method Methods 0.000 description 1
239000011541 reaction mixture Substances 0.000 description 1
238000011160 research Methods 0.000 description 1
238000010898 silica gel chromatography Methods 0.000 description 1
230000009295 sperm incapacitation Effects 0.000 description 1
238000006467 substitution reaction Methods 0.000 description 1
238000013268 sustained release Methods 0.000 description 1
239000012730 sustained-release form Substances 0.000 description 1
238000001308 synthesis method Methods 0.000 description 1
230000002194 synthesizing effect Effects 0.000 description 1
238000005303 weighing Methods 0.000 description 1
239000002023 wood Substances 0.000 description 1
229910052725 zinc Inorganic materials 0.000 description 1
239000011701 zinc Substances 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)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

JP61500751A 1985-02-04 1986-01-27 Ｌ‐ドーパの新規誘導体、その製法とそれを含有する医薬組成物 Pending JPS63501498A (ja)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
LU85757		1985-02-04
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

Publications (1)

Publication Number	Publication Date
JPS63501498A true JPS63501498A (ja)	1988-06-09

Family

ID=19730402

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
JP61500751A Pending JPS63501498A (ja)	1985-02-04	1986-01-27	Ｌ‐ドーパの新規誘導体、その製法とそれを含有する医薬組成物

Country Status (7)

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

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JP2008501704A (ja) *	2004-06-04	2008-01-24	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
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
JP2022504410A (ja) *	2018-10-08	2022-01-13	セリックスバイオプライヴェートリミテッド	パーキンソン病の処置のための組成物及び方法

Families Citing this family (10)

* 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 (en)	2004-06-04	2005-12-22	Xenoport, Inc.	Levodopa prodrugs, and compositions and uses thereof
US7563821B2 (en)	2005-12-05	2009-07-21	Xenoport, Inc.	Levodopa prodrug mesylate, compositions thereof, and uses thereof
CA2673336A1 (en)	2006-12-21	2008-06-26	Xenoport, Inc.	Levodopa dimethyl-substituted diester prodrugs, compositions, and methods of use
WO2008079387A1 (en) *	2006-12-21	2008-07-03	Xenoport, Inc.	Catechol protected levodopa diester prodrugs, compositions, and methods of use
US8399513B2 (en)	2008-10-20	2013-03-19	Xenoport, Inc.	Levodopa prodrug mesylate hydrate
US9290445B2 (en)	2008-10-20	2016-03-22	Xenoport, Inc.	Methods of synthesizing a levodopa ester prodrug
GB0904300D0 (en) *	2009-03-12	2009-04-22	Amarin Neuroscience Ltd	Essential fatty acid compounds
WO2011056240A2 (en)	2009-11-09	2011-05-12	Xenoport, Inc.	Pharmaceutical compositions and oral dosage forms of a levodopa prodrug and methods of use
CN107848954A (zh) *	2015-03-30	2018-03-27	伯里兰有限责任公司	水溶性l‑dopa酯

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DK229876A (da) *	1975-06-11	1976-12-12	Merck & Co Inc	Fremgangsmade til fremstilling af estere af alfa-methyl-3,4-dihydroxyphenylalanin
FR2365341A1 (fr) *	1976-09-28	1978-04-21	Synthelabo	Derives de l'acide l-(phenyl-3 amino-2 propionyloxy)-2 acetique
GR72800B (da) *	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/xx unknown
1986
- 1986-01-27 JP JP61500751A patent/JPS63501498A/ja active Pending
- 1986-01-27 EP EP86900721A patent/EP0250403A1/fr not_active Withdrawn
- 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

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JP2008501704A (ja) *	2004-06-04	2008-01-24	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
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
JP2022504410A (ja) *	2018-10-08	2022-01-13	セリックスバイオプライヴェートリミテッド	パーキンソン病の処置のための組成物及び方法

Also Published As

Publication number	Publication date
NO863944D0 (no)	1986-10-03
LU85757A1 (fr)	1986-09-02
NO863944L (no)	1986-12-01
DK437586D0 (da)	1986-09-12
FI871270A7 (fi)	1987-03-23
EP0250403A1 (fr)	1988-01-07
FI871270A0 (fi)	1987-03-23
WO1986004579A1 (fr)	1986-08-14
DK437586A (da)	1986-09-12

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CH631696A5 (de)	1982-08-31	Verfahren zur herstellung von olefinischen derivaten von aminosaeuren.
JP2930245B2 (ja)	1999-08-03	１，２，３，４―テトラヒドロ―９―アクリジナミンの誘導体
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US5149688A (en)	1992-09-22	Methods, compounds, and compositions for immunosuppression
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JPS62190190A (ja)	1987-08-20	Ｌ−カルニチンのホスホリルアルカノ−ルアミド誘導体類およびその医薬組成物
JPH04500506A (ja)	1992-01-30	Ａｃａｔ酵素をブロックするのに有効な二価リガンド類
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US4851448A (en)	1989-07-25	Gem-dihalo-1,8-diamino-4-aza-octanes
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JPS63501498A - Ｌ‐ドーパの新規誘導体、その製法とそれを含有する医薬組成物 - Google Patents

Info

Links

Classifications

Landscapes

Applications Claiming Priority (2)

Publications (1)

Family

ID=19730402

Family Applications (1)

Country Status (7)

Cited By (3)

Families Citing this family (10)

Family Cites Families (4)

Cited By (3)

Also Published As

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