CA2013809C - Agent pour la prophylaxie de l'atopie, methode de preparation et d'utilisation - Google Patents

Agent pour la prophylaxie de l'atopie, methode de preparation et d'utilisation

Info

Publication number: CA2013809C
Authority: CA; Canada
Prior art keywords: gamma; linolenic acid; dihomo; atopy; pge1
Prior art date: 1989-04-04
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.): Expired - Fee Related

Application number

CA002013809A

Other languages

English (en)

Other versions

CA2013809A1 (fr

Inventor

Bodo Melnik

Gerd Plewig

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.)

Beiersdorf AG

Original Assignee

Beiersdorf AG

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.)

1989-04-04

Filing date

1990-04-04

Publication date

1996-12-17

1989-04-04 Priority claimed from DE3910761A external-priority patent/DE3910761A1/de

1989-04-04 Priority claimed from DE3910760A external-priority patent/DE3910760A1/de

1990-04-04 Application filed by Beiersdorf AG filed Critical Beiersdorf AG

1990-10-04 Publication of CA2013809A1 publication Critical patent/CA2013809A1/fr

1996-12-17 Application granted granted Critical

1996-12-17 Publication of CA2013809C publication Critical patent/CA2013809C/fr

2010-04-04 Anticipated expiration legal-status Critical

Status Expired - Fee Related legal-status Critical Current

Links

206010003645 Atopy Diseases 0.000 title claims abstract description 67
238000011321 prophylaxis Methods 0.000 title claims abstract description 35
238000000034 method Methods 0.000 title claims abstract description 20
229960002733 gamolenic acid Drugs 0.000 claims abstract description 58
VZCCETWTMQHEPK-UHFFFAOYSA-N gamma-Linolensaeure Natural products CCCCCC=CCC=CCC=CCCCCC(O)=O VZCCETWTMQHEPK-UHFFFAOYSA-N 0.000 claims abstract description 57
235000020664 gamma-linolenic acid Nutrition 0.000 claims abstract description 57
VZCCETWTMQHEPK-QNEBEIHSSA-N gamma-linolenic acid Chemical compound CCCCC\C=C/C\C=C/C\C=C/CCCCC(O)=O VZCCETWTMQHEPK-QNEBEIHSSA-N 0.000 claims abstract description 57
235000021298 Dihomo-γ-linolenic acid Nutrition 0.000 claims abstract description 47
HOBAELRKJCKHQD-UHFFFAOYSA-N (8Z,11Z,14Z)-8,11,14-eicosatrienoic acid Natural products CCCCCC=CCC=CCC=CCCCCCCC(O)=O HOBAELRKJCKHQD-UHFFFAOYSA-N 0.000 claims abstract description 46
HOBAELRKJCKHQD-QNEBEIHSSA-N dihomo-γ-linolenic acid Chemical compound CCCCC\C=C/C\C=C/C\C=C/CCCCCCC(O)=O HOBAELRKJCKHQD-QNEBEIHSSA-N 0.000 claims abstract description 46
239000000126 substance Substances 0.000 claims abstract description 41
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239000003795 chemical substances by application Substances 0.000 claims abstract description 38
150000001408 amides Chemical class 0.000 claims abstract description 33
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GMVPRGQOIOIIMI-DWKJAMRDSA-N prostaglandin E1 Chemical compound CCCCC[C@H](O)\C=C\[C@H]1[C@H](O)CC(=O)[C@@H]1CCCCCCC(O)=O GMVPRGQOIOIIMI-DWKJAMRDSA-N 0.000 claims abstract description 13
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XEYBRNLFEZDVAW-UHFFFAOYSA-N prostaglandin E2 Natural products CCCCCC(O)C=CC1C(O)CC(=O)C1CC=CCCCC(O)=O XEYBRNLFEZDVAW-UHFFFAOYSA-N 0.000 claims abstract description 8
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IUKXMNDGTWTNTP-RHDCIPCHSA-N 15-HETrE Chemical compound CCCCCC(O)\C=C\C=C/C\C=C/CCCCCCC(O)=O IUKXMNDGTWTNTP-RHDCIPCHSA-N 0.000 claims abstract description 4
CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 claims description 14
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GVJHHUAWPYXKBD-IEOSBIPESA-N α-tocopherol Chemical compound OC1=C(C)C(C)=C2O[C@@](CCC[C@H](C)CCC[C@H](C)CCCC(C)C)(C)CCC2=C1C GVJHHUAWPYXKBD-IEOSBIPESA-N 0.000 claims description 8
OYHQOLUKZRVURQ-HZJYTTRNSA-N Linoleic acid Chemical compound CCCCC\C=C/C\C=C/CCCCCCCC(O)=O OYHQOLUKZRVURQ-HZJYTTRNSA-N 0.000 claims description 7
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OYHQOLUKZRVURQ-IXWMQOLASA-N linoleic acid Natural products CCCCC\C=C/C\C=C\CCCCCCCC(O)=O OYHQOLUKZRVURQ-IXWMQOLASA-N 0.000 claims description 5
GVJHHUAWPYXKBD-UHFFFAOYSA-N (±)-α-Tocopherol Chemical compound OC1=C(C)C(C)=C2OC(CCCC(C)CCCC(C)CCCC(C)C)(C)CCC2=C1C GVJHHUAWPYXKBD-UHFFFAOYSA-N 0.000 claims description 4
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XEYBRNLFEZDVAW-ARSRFYASSA-N dinoprostone Chemical compound CCCCC[C@H](O)\C=C\[C@H]1[C@H](O)CC(=O)[C@@H]1C\C=C/CCCC(O)=O XEYBRNLFEZDVAW-ARSRFYASSA-N 0.000 claims description 2
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WIGCFUFOHFEKBI-UHFFFAOYSA-N gamma-tocopherol Natural products CC(C)CCCC(C)CCCC(C)CCCC1CCC2C(C)C(O)C(C)C(C)C2O1 WIGCFUFOHFEKBI-UHFFFAOYSA-N 0.000 claims description 2
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102100034544 Acyl-CoA 6-desaturase Human genes 0.000 description 3
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239000010475 evening primrose oil Substances 0.000 description 3
239000000203 mixture Substances 0.000 description 3
LIFNDDBLJFPEAN-BPSSIEEOSA-N (2s)-4-amino-2-[[(2s)-2-[[2-[[2-[[(2s)-5-amino-2-[[(2s)-2-[[(2s)-6-amino-2-[[(2s)-2-[[(2s)-5-oxopyrrolidine-2-carbonyl]amino]propanoyl]amino]hexanoyl]amino]-3-hydroxypropanoyl]amino]-5-oxopentanoyl]amino]acetyl]amino]acetyl]amino]-3-hydroxypropanoyl]amino Chemical compound NC(=O)C[C@@H](C(O)=O)NC(=O)[C@H](CO)NC(=O)CNC(=O)CNC(=O)[C@H](CCC(N)=O)NC(=O)[C@H](CO)NC(=O)[C@H](CCCCN)NC(=O)[C@H](C)NC(=O)[C@@H]1CCC(=O)N1 LIFNDDBLJFPEAN-BPSSIEEOSA-N 0.000 description 2
108010003422 Circulating Thymic Factor Proteins 0.000 description 2
206010012438 Dermatitis atopic Diseases 0.000 description 2
NTYJJOPFIAHURM-UHFFFAOYSA-N Histamine Chemical compound NCCC1=CN=CN1 NTYJJOPFIAHURM-UHFFFAOYSA-N 0.000 description 2
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102100023981 Lamina-associated polypeptide 2, isoform alpha Human genes 0.000 description 2
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235000016954 Ribes hudsonianum Nutrition 0.000 description 2
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DTOSIQBPPRVQHS-PDBXOOCHSA-N alpha-linolenic acid Chemical compound CC\C=C/C\C=C/C\C=C/CCCCCCCC(O)=O DTOSIQBPPRVQHS-PDBXOOCHSA-N 0.000 description 2
YZXBAPSDXZZRGB-DOFZRALJSA-N arachidonic acid Chemical compound CCCCC\C=C/C\C=C/C\C=C/C\C=C/CCCC(O)=O YZXBAPSDXZZRGB-DOFZRALJSA-N 0.000 description 2
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230000008901 benefit Effects 0.000 description 2
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230000003750 conditioning effect Effects 0.000 description 2
239000005556 hormone Substances 0.000 description 2
229940088597 hormone Drugs 0.000 description 2
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238000011835 investigation Methods 0.000 description 2
229940094443 oxytocics prostaglandins Drugs 0.000 description 2
238000002360 preparation method Methods 0.000 description 2
QZAYGJVTTNCVMB-UHFFFAOYSA-N serotonin Chemical compound C1=C(O)C=C2C(CCN)=CNC2=C1 QZAYGJVTTNCVMB-UHFFFAOYSA-N 0.000 description 2
208000024891 symptom Diseases 0.000 description 2
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208000035285 Allergic Seasonal Rhinitis Diseases 0.000 description 1
241000428352 Amma Species 0.000 description 1
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QXZGBUJJYSLZLT-UHFFFAOYSA-N H-Arg-Pro-Pro-Gly-Phe-Ser-Pro-Phe-Arg-OH Natural products NC(N)=NCCCC(N)C(=O)N1CCCC1C(=O)N1C(C(=O)NCC(=O)NC(CC=2C=CC=CC=2)C(=O)NC(CO)C(=O)N2C(CCC2)C(=O)NC(CC=2C=CC=CC=2)C(=O)NC(CCCN=C(N)N)C(O)=O)CCC1 QXZGBUJJYSLZLT-UHFFFAOYSA-N 0.000 description 1
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YRTISBKUCLDRGF-ADVSENJOSA-N acetic acid;(3s)-3-[[(2s)-6-amino-2-[[(2s)-2-amino-5-(diaminomethylideneamino)pentanoyl]amino]hexanoyl]amino]-4-[[(2s)-1-[[(1s)-1-carboxy-2-(4-hydroxyphenyl)ethyl]amino]-3-methyl-1-oxobutan-2-yl]amino]-4-oxobutanoic acid Chemical compound CC(O)=O.NC(N)=NCCC[C@H](N)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CC(O)=O)C(=O)N[C@@H](C(C)C)C(=O)N[C@H](C(O)=O)CC1=CC=C(O)C=C1 YRTISBKUCLDRGF-ADVSENJOSA-N 0.000 description 1
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QXZGBUJJYSLZLT-FDISYFBBSA-N bradykinin Chemical compound NC(=N)NCCC[C@H](N)C(=O)N1CCC[C@H]1C(=O)N1[C@H](C(=O)NCC(=O)N[C@@H](CC=2C=CC=CC=2)C(=O)N[C@@H](CO)C(=O)N2[C@@H](CCC2)C(=O)N[C@@H](CC=2C=CC=CC=2)C(=O)N[C@@H](CCCNC(N)=N)C(O)=O)CCC1 QXZGBUJJYSLZLT-FDISYFBBSA-N 0.000 description 1
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235000015110 jellies Nutrition 0.000 description 1
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230000009862 primary prevention Effects 0.000 description 1
230000002035 prolonged effect Effects 0.000 description 1
230000000069 prophylactic effect Effects 0.000 description 1
HFHDHCJBZVLPGP-UHFFFAOYSA-N schardinger α-dextrin Chemical compound O1C(C(C2O)O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC(C(O)C2O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC2C(O)C(O)C1OC2CO HFHDHCJBZVLPGP-UHFFFAOYSA-N 0.000 description 1
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238000003786 synthesis reaction Methods 0.000 description 1
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238000002560 therapeutic procedure Methods 0.000 description 1
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Landscapes

Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Cosmetics (AREA)

CA002013809A 1989-04-04 1990-04-04 Agent pour la prophylaxie de l'atopie, methode de preparation et d'utilisation Expired - Fee Related CA2013809C (fr)

Applications Claiming Priority (6)

Application Number	Priority Date	Filing Date	Title
DEP3910761.2		1989-04-04
DEP3910760.4		1989-04-04
DE3910761A DE3910761A1 (de)	1989-04-04	1989-04-04	Mittel zur atopie-prophylaxe
DE3910760A DE3910760A1 (de)	1989-04-04	1989-04-04	Neue verwendung bekannter substanzen sowie verfahren zur herstellung von geeigneten praeparaten
DEP3930816.2		1989-09-14
DE3930816		1989-09-14

Publications (2)

Publication Number	Publication Date
CA2013809A1 CA2013809A1 (fr)	1990-10-04
CA2013809C true CA2013809C (fr)	1996-12-17

Family

ID=27199345

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA002013809A Expired - Fee Related CA2013809C (fr)	1989-04-04	1990-04-04	Agent pour la prophylaxie de l'atopie, methode de preparation et d'utilisation

Country Status (1)

Country	Link
CA (1)	CA2013809C (fr)

1990
- 1990-04-04 CA CA002013809A patent/CA2013809C/fr not_active Expired - Fee Related

Also Published As

Publication number	Publication date
CA2013809A1 (fr)	1990-10-04

Legal Events

Date	Code	Title	Description
1992-09-28	EEER	Examination request
2003-04-04	MKLA	Lapsed

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