CA1130302A - 5-methoxy-psoralen, nouveau medicament, et methode de synthese - Google Patents

5-methoxy-psoralen, nouveau medicament, et methode de synthese

Info

Publication number: CA1130302A
Authority: CA; Canada
Prior art keywords: methoxy; psoralen; phloroglucinol; hydroxy; coumaranone
Prior art date: 1977-10-21
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

CA394,203A

Other languages

English (en)

Inventor

Jean-Jacques Goupil

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.)

Individual

Original Assignee

Individual

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.)

1977-10-21

Filing date

1982-01-14

Publication date

1982-08-24

1977-10-21 Priority claimed from FR7731719A external-priority patent/FR2406444A1/fr

1977-12-09 Priority claimed from FR7737144A external-priority patent/FR2411193A1/fr

1978-10-23 Priority claimed from CA000313995A external-priority patent/CA1121269A/fr

1982-01-14 Application filed by Individual filed Critical Individual

1982-01-14 Priority to CA394,203A priority Critical patent/CA1130302A/fr

1982-08-24 Application granted granted Critical

1982-08-24 Publication of CA1130302A publication Critical patent/CA1130302A/fr

1992-05-04 Priority claimed from US07/879,539 external-priority patent/US5360816A/en

Status Expired legal-status Critical Current

Links

BGEBZHIAGXMEMV-UHFFFAOYSA-N 5-methoxypsoralen Chemical compound O1C(=O)C=CC2=C1C=C1OC=CC1=C2OC BGEBZHIAGXMEMV-UHFFFAOYSA-N 0.000 title claims abstract description 102
SQBBOVROCFXYBN-UHFFFAOYSA-N methoxypsoralen Natural products C1=C2OC(=O)C(OC)=CC2=CC2=C1OC=C2 SQBBOVROCFXYBN-UHFFFAOYSA-N 0.000 title claims abstract description 67
229960002045 bergapten Drugs 0.000 title claims abstract description 57
KGZDKFWCIPZMRK-UHFFFAOYSA-N bergapten Natural products COC1C2=C(Cc3ccoc13)C=CC(=O)O2 KGZDKFWCIPZMRK-UHFFFAOYSA-N 0.000 title claims abstract description 51
238000000034 method Methods 0.000 title claims abstract description 25
230000008569 process Effects 0.000 title claims abstract description 18
239000003814 drug Substances 0.000 title description 15
238000003786 synthesis reaction Methods 0.000 title description 8
230000015572 biosynthetic process Effects 0.000 title description 6
LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 claims abstract description 17
JPYHHZQJCSQRJY-UHFFFAOYSA-N Phloroglucinol Natural products CCC=CCC=CCC=CCC=CCCCCC(=O)C1=C(O)C=C(O)C=C1O JPYHHZQJCSQRJY-UHFFFAOYSA-N 0.000 claims abstract description 16
QCDYQQDYXPDABM-UHFFFAOYSA-N phloroglucinol Chemical compound OC1=CC(O)=CC(O)=C1 QCDYQQDYXPDABM-UHFFFAOYSA-N 0.000 claims abstract description 16
229960001553 phloroglucinol Drugs 0.000 claims abstract description 16
OZCXNEVVUVPIQX-UHFFFAOYSA-N 6-hydroxy-4-methoxy-1-benzofuran-3-one Chemical compound COC1=CC(O)=CC2=C1C(=O)CO2 OZCXNEVVUVPIQX-UHFFFAOYSA-N 0.000 claims abstract description 12
RYHZYFZJDXSIID-UHFFFAOYSA-N 4-methoxy-2,3-dihydro-1-benzofuran-6-ol Chemical compound COC1=CC(O)=CC2=C1CCO2 RYHZYFZJDXSIID-UHFFFAOYSA-N 0.000 claims abstract description 7
HDVRLUFGYQYLFJ-UHFFFAOYSA-N flamenol Chemical compound COC1=CC(O)=CC(O)=C1 HDVRLUFGYQYLFJ-UHFFFAOYSA-N 0.000 claims abstract description 6
230000002194 synthesizing effect Effects 0.000 claims abstract description 4
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RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 29
239000000203 mixture Substances 0.000 claims description 23
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 18
JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 claims description 14
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 12
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 12
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NWZSZGALRFJKBT-KNIFDHDWSA-N (2s)-2,6-diaminohexanoic acid;(2s)-2-hydroxybutanedioic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O.NCCCC[C@H](N)C(O)=O NWZSZGALRFJKBT-KNIFDHDWSA-N 0.000 claims description 6
IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 claims description 6
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235000011056 potassium acetate Nutrition 0.000 claims description 4
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XPYQFIISZQCINN-QVXDJYSKSA-N 4-amino-1-[(2r,3e,4s,5r)-3-(fluoromethylidene)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]pyrimidin-2-one;hydrate Chemical compound O.O=C1N=C(N)C=CN1[C@H]1C(=C/F)/[C@H](O)[C@@H](CO)O1 XPYQFIISZQCINN-QVXDJYSKSA-N 0.000 claims 1
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ZCCUUQDIBDJBTK-UHFFFAOYSA-N psoralen Chemical compound C1=C2OC(=O)C=CC2=CC2=C1OC=C2 ZCCUUQDIBDJBTK-UHFFFAOYSA-N 0.000 description 22
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BUNGCZLFHHXKBX-UHFFFAOYSA-N 8-methoxypsoralen Natural products C1=CC(=O)OC2=C1C=C1CCOC1=C2OC BUNGCZLFHHXKBX-UHFFFAOYSA-N 0.000 description 14
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YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 4
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UGNWTBMOAKPKBL-UHFFFAOYSA-N tetrachloro-1,4-benzoquinone Chemical compound ClC1=C(Cl)C(=O)C(Cl)=C(Cl)C1=O UGNWTBMOAKPKBL-UHFFFAOYSA-N 0.000 description 3
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229910052708 sodium Inorganic materials 0.000 description 1
235000017557 sodium bicarbonate Nutrition 0.000 description 1
229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
235000019333 sodium laurylsulphate Nutrition 0.000 description 1
238000001228 spectrum Methods 0.000 description 1
239000008107 starch Substances 0.000 description 1
235000019698 starch Nutrition 0.000 description 1
239000000126 substance Substances 0.000 description 1
238000000967 suction filtration Methods 0.000 description 1
239000004094 surface-active agent Substances 0.000 description 1
229940124597 therapeutic agent Drugs 0.000 description 1
238000011200 topical administration Methods 0.000 description 1
230000000699 topical effect Effects 0.000 description 1
230000002110 toxicologic effect Effects 0.000 description 1
231100000027 toxicology Toxicity 0.000 description 1
231100000041 toxicology testing Toxicity 0.000 description 1
238000002211 ultraviolet spectrum Methods 0.000 description 1
229940099259 vaseline Drugs 0.000 description 1
239000010497 wheat germ oil Substances 0.000 description 1

Landscapes

Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

CA394,203A 1977-10-21 1982-01-14 5-methoxy-psoralen, nouveau medicament, et methode de synthese Expired CA1130302A (fr)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
CA394,203A CA1130302A (fr)	1977-10-21	1982-01-14	5-methoxy-psoralen, nouveau medicament, et methode de synthese

Applications Claiming Priority (7)

Application Number	Priority Date	Filing Date	Title
FR7731719A FR2406444A1 (fr)	1977-10-21	1977-10-21	Nouveau medicament contenant un derive du psoralene
FR77.31.719		1977-10-21
FR77.37144		1977-12-09
FR7737144A FR2411193A1 (fr)	1977-12-09	1977-12-09	Procede de preparation du 5-metoxy-psoralene
CA000313995A CA1121269A (fr)	1977-10-21	1978-10-23	5-methoxy-psoralen, nouveau medicament et procede de synthese
CA394,203A CA1130302A (fr)	1977-10-21	1982-01-14	5-methoxy-psoralen, nouveau medicament, et methode de synthese
US07/879,539 US5360816A (en)	1977-05-05	1992-05-04	5-methoxy psoralen used to treat psoriasis

Publications (1)

Publication Number	Publication Date
CA1130302A true CA1130302A (fr)	1982-08-24

Family

ID=27508126

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA394,203A Expired CA1130302A (fr)	1977-10-21	1982-01-14	5-methoxy-psoralen, nouveau medicament, et methode de synthese

Country Status (1)

Country	Link
CA (1)	CA1130302A (fr)

1982
- 1982-01-14 CA CA394,203A patent/CA1130302A/fr not_active Expired

Legal Events

Date	Code	Title	Description
1999-08-24	MKEX	Expiry

Publication	Publication Date	Title
US5132101A (en)	1992-07-21	Acetylene-cumulene porphycene compounds for photodynamic therapy
US5179120A (en)	1993-01-12	Porphycene compounds for photodynamic therapy
CA1121269A (fr)	1982-04-06	5-methoxy-psoralen, nouveau medicament et procede de synthese
EP0354594A2 (fr)	1990-02-14	Dérivés de la physostigmine, ayant des propriétés inhibitrices d'acétylcholinestérase et procédé de préparation correspondant
Gschwend et al.	1976	Intramolecular Diels-Alder reactions. Synthesis of 3a-phenylisoindolines as analgetic templates
EP0569507A1 (fr)	1993-11-18	Derives de porphycene s'utilisant directement en therapie photodynamique ou comme intermediaires de synthese de colorants photoactivables appropries en therapie photodynamique
EP1279676A1 (fr)	2003-01-29	Dérivés de porphyrines pour la thérapie photodynamique
JPS6126996B2 (fr)	1986-06-23
CA1130302A (fr)	1982-08-24	5-methoxy-psoralen, nouveau medicament, et methode de synthese
US5405868A (en)	1995-04-11	5-methoxy-psoralen as new medicament and process for the synthesis thereof
SU1468424A3 (ru)	1989-03-23	Способ получени производных гидантоина
DE69806189T2 (de)	2003-02-13	Acronycinderivate, verfahren zu ihrer herstellung und diese enthaltende pharmazeutische zubereitungen
JPH02502543A (ja)	1990-08-16	新規６置換マイトマイシン類似体
EP0088023B1 (fr)	1987-01-14	Pyrido(3',4':4,5) furo(3,2-g) coumarines ou pyrido(3,4-h) psoralènes,obtention, applications en cosmétologie et à titre de médicaments, et compositions cosmétiques et pharmaceutiques les contenant
US4696941A (en)	1987-09-29	1,8-diacyloxy-10-acylanthrones
JP2006514064A (ja)	2006-04-27	ポルフィリン誘導体
FR2413358A1 (fr)	1979-07-27	Nouveaux derives de 2-aminomethylphenol, utiles notamment comme agents anti-inflammatoires, et leur procede de preparation
DE2632118A1 (de)	1977-01-20	Apovincaminolester und verfahren zu deren herstellung
JPS61246185A (ja)	1986-11-01	５−メトキシ−プソラレンの製造方法
IE47460B1 (en)	1984-03-21	5-methoxy-psoralen as new medicament and process for the synthesis thereof
US5306825A (en)	1994-04-26	Physostigmine derivatives with acetylcholinesterase inhibition properties, and the relative production process
WO1996031451A1 (fr)	1996-10-10	Porphycenes substitues en position 9
JPH10502088A (ja)	1998-02-24	ブレフェルジンａの新しい誘導体およびがん治療におけるそれらの有用性
JPH0517448A (ja)	1993-01-26	１４−Ｏ−ｐ−クロロベンゾイルアコニンおよび鎮痛・抗炎症剤
JPS6050785B2 (ja)	1985-11-11	ピリドキシン酸誘導体の製造方法