CA1334576C - Compositions pharmaceutiques antivirales et procede de preparation - Google Patents

Compositions pharmaceutiques antivirales et procede de preparation

Info

Publication number: CA1334576C
Authority: CA; Canada
Prior art keywords: acid; fatty acid; amino acid; omega; derivative
Prior art date: 1988-03-09
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

CA000593270A

Other languages

English (en)

Inventor

Istvan Racz

Gyongyver Soos

Miklos Koller

Peter Literati Nagy

Maria Boros

Jeno Szilbereky

Gabor Nemeth

Alan Pinter

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.)

BIOREX KFT

Original Assignee

BIOREX KFT

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.)

1988-03-09

Filing date

1989-03-09

Publication date

1995-02-28

1989-03-09 Application filed by BIOREX KFT filed Critical BIOREX KFT

1995-02-28 Application granted granted Critical

1995-02-28 Publication of CA1334576C publication Critical patent/CA1334576C/fr

2012-02-28 Anticipated expiration legal-status Critical

Status Expired - Fee Related legal-status Critical Current

Links

230000000840 anti-viral effect Effects 0.000 title claims abstract description 15
239000008194 pharmaceutical composition Substances 0.000 title claims abstract description 14
238000004519 manufacturing process Methods 0.000 title description 3
239000000203 mixture Substances 0.000 claims abstract description 47
238000000034 method Methods 0.000 claims abstract description 28
230000008569 process Effects 0.000 claims abstract description 27
150000001413 amino acids Chemical class 0.000 claims abstract description 24
235000014113 dietary fatty acids Nutrition 0.000 claims abstract description 23
229930195729 fatty acid Natural products 0.000 claims abstract description 23
239000000194 fatty acid Substances 0.000 claims abstract description 23
150000004665 fatty acids Chemical class 0.000 claims abstract description 23
230000003308 immunostimulating effect Effects 0.000 claims abstract description 11
QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims abstract description 6
229910052783 alkali metal Inorganic materials 0.000 claims abstract description 6
150000001340 alkali metals Chemical class 0.000 claims abstract description 6
229910052784 alkaline earth metal Inorganic materials 0.000 claims abstract description 6
125000003277 amino group Chemical group 0.000 claims abstract description 6
239000003963 antioxidant agent Substances 0.000 claims abstract description 6
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims abstract description 6
150000003839 salts Chemical class 0.000 claims abstract description 6
239000000654 additive Substances 0.000 claims abstract description 5
238000002360 preparation method Methods 0.000 claims abstract description 5
125000004178 (C1-C4) alkyl group Chemical group 0.000 claims abstract 3
KDXKERNSBIXSRK-YFKPBYRVSA-N L-lysine Chemical compound NCCCC[C@H](N)C(O)=O KDXKERNSBIXSRK-YFKPBYRVSA-N 0.000 claims description 40
239000004472 Lysine Substances 0.000 claims description 23
235000001014 amino acid Nutrition 0.000 claims description 22
JAZBEHYOTPTENJ-JLNKQSITSA-N all-cis-5,8,11,14,17-icosapentaenoic acid Chemical compound CC\C=C/C\C=C/C\C=C/C\C=C/C\C=C/CCCC(O)=O JAZBEHYOTPTENJ-JLNKQSITSA-N 0.000 claims description 21
JAZBEHYOTPTENJ-UHFFFAOYSA-N eicosapentaenoic acid Natural products CCC=CCC=CCC=CCC=CCC=CCCCC(O)=O JAZBEHYOTPTENJ-UHFFFAOYSA-N 0.000 claims description 21
MBMBGCFOFBJSGT-KUBAVDMBSA-N all-cis-docosa-4,7,10,13,16,19-hexaenoic acid Chemical compound CC\C=C/C\C=C/C\C=C/C\C=C/C\C=C/C\C=C/CCC(O)=O MBMBGCFOFBJSGT-KUBAVDMBSA-N 0.000 claims description 19
235000019766 L-Lysine Nutrition 0.000 claims description 17
OUYCCCASQSFEME-UHFFFAOYSA-N tyrosine Chemical compound OC(=O)C(N)CC1=CC=C(O)C=C1 OUYCCCASQSFEME-UHFFFAOYSA-N 0.000 claims description 3
230000001131 transforming effect Effects 0.000 claims description 2
239000003937 drug carrier Substances 0.000 claims 2
235000021323 fish oil Nutrition 0.000 claims 2
239000004480 active ingredient Substances 0.000 abstract description 6
125000000217 alkyl group Chemical group 0.000 abstract description 5
150000001875 compounds Chemical class 0.000 abstract description 5
239000000969 carrier Substances 0.000 abstract description 3
150000004677 hydrates Chemical class 0.000 abstract description 2
229960001438 immunostimulant agent Drugs 0.000 abstract description 2
239000003022 immunostimulating agent Substances 0.000 abstract description 2
229960003646 lysine Drugs 0.000 description 21
229960005135 eicosapentaenoic acid Drugs 0.000 description 18
235000020673 eicosapentaenoic acid Nutrition 0.000 description 17
241000700605 Viruses Species 0.000 description 12
229940024606 amino acid Drugs 0.000 description 12
235000020777 polyunsaturated fatty acids Nutrition 0.000 description 12
239000000243 solution Substances 0.000 description 12
238000012360 testing method Methods 0.000 description 11
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 description 8
AHLPHDHHMVZTML-BYPYZUCNSA-N L-Ornithine Chemical compound NCCC[C@H](N)C(O)=O AHLPHDHHMVZTML-BYPYZUCNSA-N 0.000 description 8
235000020669 docosahexaenoic acid Nutrition 0.000 description 8
230000012010 growth Effects 0.000 description 8
229940090949 docosahexaenoic acid Drugs 0.000 description 7
OUYCCCASQSFEME-QMMMGPOBSA-N L-tyrosine Chemical compound OC(=O)[C@@H](N)CC1=CC=C(O)C=C1 OUYCCCASQSFEME-QMMMGPOBSA-N 0.000 description 6
KDXKERNSBIXSRK-UHFFFAOYSA-N Lysine Natural products NCCCCC(N)C(O)=O KDXKERNSBIXSRK-UHFFFAOYSA-N 0.000 description 6
230000000694 effects Effects 0.000 description 6
235000018977 lysine Nutrition 0.000 description 6
HZRUTVAFDWTKGD-JEDNCBNOSA-N (2s)-2,6-diaminohexanoic acid;hydrate Chemical compound O.NCCCC[C@H](N)C(O)=O HZRUTVAFDWTKGD-JEDNCBNOSA-N 0.000 description 5
AHLPHDHHMVZTML-UHFFFAOYSA-N Orn-delta-NH2 Natural products NCCCC(N)C(O)=O AHLPHDHHMVZTML-UHFFFAOYSA-N 0.000 description 5
210000004027 cell Anatomy 0.000 description 5
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108010062580 Concanavalin A Proteins 0.000 description 4
HNDVDQJCIGZPNO-YFKPBYRVSA-N L-histidine Chemical compound OC(=O)[C@@H](N)CC1=CN=CN1 HNDVDQJCIGZPNO-YFKPBYRVSA-N 0.000 description 4
229930003427 Vitamin E Natural products 0.000 description 4
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 description 4
HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 4
230000029812 viral genome replication Effects 0.000 description 4
235000019165 vitamin E Nutrition 0.000 description 4
239000011709 vitamin E Substances 0.000 description 4
229940046009 vitamin E Drugs 0.000 description 4
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
230000009471 action Effects 0.000 description 3
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235000021122 unsaturated fatty acids Nutrition 0.000 description 3
150000004670 unsaturated fatty acids Chemical class 0.000 description 3
MTCFGRXMJLQNBG-REOHCLBHSA-N (2S)-2-Amino-3-hydroxypropansäure Chemical compound OC[C@H](N)C(O)=O MTCFGRXMJLQNBG-REOHCLBHSA-N 0.000 description 2
241000251468 Actinopterygii Species 0.000 description 2
CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
238000012404 In vitro experiment Methods 0.000 description 2
AYFVYJQAPQTCCC-GBXIJSLDSA-N L-threonine Chemical compound C[C@@H](O)[C@H](N)C(O)=O AYFVYJQAPQTCCC-GBXIJSLDSA-N 0.000 description 2
GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 2
UTJLXEIPEHZYQJ-UHFFFAOYSA-N Ornithine Natural products OC(=O)C(C)CCCN UTJLXEIPEHZYQJ-UHFFFAOYSA-N 0.000 description 2
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
229920002472 Starch Polymers 0.000 description 2
MKUXAQIIEYXACX-UHFFFAOYSA-N aciclovir Chemical compound N1C(N)=NC(=O)C2=C1N(COCCO)C=N2 MKUXAQIIEYXACX-UHFFFAOYSA-N 0.000 description 2
229960004150 aciclovir Drugs 0.000 description 2
239000003443 antiviral agent Substances 0.000 description 2
239000002775 capsule Substances 0.000 description 2
235000005911 diet Nutrition 0.000 description 2
230000037213 diet Effects 0.000 description 2
235000020776 essential amino acid Nutrition 0.000 description 2
239000003797 essential amino acid Substances 0.000 description 2
238000002474 experimental method Methods 0.000 description 2
235000019688 fish Nutrition 0.000 description 2
RWSXRVCMGQZWBV-WDSKDSINSA-N glutathione Chemical compound OC(=O)[C@@H](N)CCC(=O)N[C@@H](CS)C(=O)NCC(O)=O RWSXRVCMGQZWBV-WDSKDSINSA-N 0.000 description 2
HNDVDQJCIGZPNO-UHFFFAOYSA-N histidine Natural products OC(=O)C(N)CC1=CN=CN1 HNDVDQJCIGZPNO-UHFFFAOYSA-N 0.000 description 2
210000000987 immune system Anatomy 0.000 description 2
238000000338 in vitro Methods 0.000 description 2
208000015181 infectious disease Diseases 0.000 description 2
238000011835 investigation Methods 0.000 description 2
239000008101 lactose Substances 0.000 description 2
235000019359 magnesium stearate Nutrition 0.000 description 2
230000010076 replication Effects 0.000 description 2
FSYKKLYZXJSNPZ-UHFFFAOYSA-N sarcosine Chemical compound C[NH2+]CC([O-])=O FSYKKLYZXJSNPZ-UHFFFAOYSA-N 0.000 description 2
239000008107 starch Substances 0.000 description 2
235000019698 starch Nutrition 0.000 description 2
239000011550 stock solution Substances 0.000 description 2
XOAAWQZATWQOTB-UHFFFAOYSA-N taurine Chemical compound NCCS(O)(=O)=O XOAAWQZATWQOTB-UHFFFAOYSA-N 0.000 description 2
229960005486 vaccine Drugs 0.000 description 2
230000009385 viral infection Effects 0.000 description 2
DVSZKTAMJJTWFG-SKCDLICFSA-N (2e,4e,6e,8e,10e,12e)-docosa-2,4,6,8,10,12-hexaenoic acid Chemical compound CCCCCCCCC\C=C\C=C\C=C\C=C\C=C\C=C\C(O)=O DVSZKTAMJJTWFG-SKCDLICFSA-N 0.000 description 1
UKAUYVFTDYCKQA-UHFFFAOYSA-N -2-Amino-4-hydroxybutanoic acid Natural products OC(=O)C(N)CCO UKAUYVFTDYCKQA-UHFFFAOYSA-N 0.000 description 1
KWTQSFXGGICVPE-UHFFFAOYSA-N 2-amino-5-(diaminomethylideneamino)pentanoic acid;hydron;chloride Chemical compound Cl.OC(=O)C(N)CCCN=C(N)N KWTQSFXGGICVPE-UHFFFAOYSA-N 0.000 description 1
GZJLLYHBALOKEX-UHFFFAOYSA-N 6-Ketone, O18-Me-Ussuriedine Natural products CC=CCC=CCC=CCC=CCC=CCC=CCCCC(O)=O GZJLLYHBALOKEX-UHFFFAOYSA-N 0.000 description 1
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206010003210 Arteriosclerosis Diseases 0.000 description 1
241000972773 Aulopiformes Species 0.000 description 1
NLZUEZXRPGMBCV-UHFFFAOYSA-N Butylhydroxytoluene Chemical compound CC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 NLZUEZXRPGMBCV-UHFFFAOYSA-N 0.000 description 1
241000700198 Cavia Species 0.000 description 1
DYDCUQKUCUHJBH-UWTATZPHSA-N D-Cycloserine Chemical compound N[C@@H]1CONC1=O DYDCUQKUCUHJBH-UWTATZPHSA-N 0.000 description 1
DYDCUQKUCUHJBH-UHFFFAOYSA-N D-Cycloserine Natural products NC1CONC1=O DYDCUQKUCUHJBH-UHFFFAOYSA-N 0.000 description 1
CKLJMWTZIZZHCS-UHFFFAOYSA-N D-OH-Asp Natural products OC(=O)C(N)CC(O)=O CKLJMWTZIZZHCS-UHFFFAOYSA-N 0.000 description 1
-1 EPA and OHA Chemical class 0.000 description 1
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239000001828 Gelatine Substances 0.000 description 1
108010024636 Glutathione Proteins 0.000 description 1
208000029433 Herpesviridae infectious disease Diseases 0.000 description 1
241000598436 Human T-cell lymphotropic virus Species 0.000 description 1
LCWXJXMHJVIJFK-UHFFFAOYSA-N Hydroxylysine Natural products NCC(O)CC(N)CC(O)=O LCWXJXMHJVIJFK-UHFFFAOYSA-N 0.000 description 1
PMMYEEVYMWASQN-DMTCNVIQSA-N Hydroxyproline Chemical compound O[C@H]1CN[C@H](C(O)=O)C1 PMMYEEVYMWASQN-DMTCNVIQSA-N 0.000 description 1
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
206010021460 Immunodeficiency syndromes Diseases 0.000 description 1
CKLJMWTZIZZHCS-UWTATZPHSA-N L-Aspartic acid Natural products OC(=O)[C@H](N)CC(O)=O CKLJMWTZIZZHCS-UWTATZPHSA-N 0.000 description 1
CKLJMWTZIZZHCS-REOHCLBHSA-N L-aspartic acid Chemical compound OC(=O)[C@@H](N)CC(O)=O CKLJMWTZIZZHCS-REOHCLBHSA-N 0.000 description 1
FSBIGDSBMBYOPN-VKHMYHEASA-N L-canavanine Chemical compound OC(=O)[C@@H](N)CCONC(N)=N FSBIGDSBMBYOPN-VKHMYHEASA-N 0.000 description 1
ZDXPYRJPNDTMRX-VKHMYHEASA-N L-glutamine Chemical compound OC(=O)[C@@H](N)CCC(N)=O ZDXPYRJPNDTMRX-VKHMYHEASA-N 0.000 description 1
229930182816 L-glutamine Natural products 0.000 description 1
FFFHZYDWPBMWHY-VKHMYHEASA-N L-homocysteine Chemical compound OC(=O)[C@@H](N)CCS FFFHZYDWPBMWHY-VKHMYHEASA-N 0.000 description 1
UKAUYVFTDYCKQA-VKHMYHEASA-N L-homoserine Chemical compound OC(=O)[C@@H](N)CCO UKAUYVFTDYCKQA-VKHMYHEASA-N 0.000 description 1
241001465754 Metazoa Species 0.000 description 1
241000699670 Mus sp. Species 0.000 description 1
FSBIGDSBMBYOPN-UHFFFAOYSA-N O-guanidino-DL-homoserine Natural products OC(=O)C(N)CCON=C(N)N FSBIGDSBMBYOPN-UHFFFAOYSA-N 0.000 description 1
108010058846 Ovalbumin Proteins 0.000 description 1
208000037273 Pathologic Processes Diseases 0.000 description 1
NPYPAHLBTDXSSS-UHFFFAOYSA-N Potassium ion Chemical compound [K+] NPYPAHLBTDXSSS-UHFFFAOYSA-N 0.000 description 1
108010077895 Sarcosine Proteins 0.000 description 1
241001125046 Sardina pilchardus Species 0.000 description 1
241000700584 Simplexvirus Species 0.000 description 1
239000004473 Threonine Substances 0.000 description 1
IQFYYKKMVGJFEH-XLPZGREQSA-N Thymidine Chemical compound O=C1NC(=O)C(C)=CN1[C@@H]1O[C@H](CO)[C@@H](O)C1 IQFYYKKMVGJFEH-XLPZGREQSA-N 0.000 description 1
230000004913 activation Effects 0.000 description 1
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230000032683 aging Effects 0.000 description 1
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230000005875 antibody response Effects 0.000 description 1
239000004599 antimicrobial Substances 0.000 description 1
YZXBAPSDXZZRGB-DOFZRALJSA-N arachidonic acid Chemical class CCCCC\C=C/C\C=C/C\C=C/C\C=C/CCCC(O)=O YZXBAPSDXZZRGB-DOFZRALJSA-N 0.000 description 1
208000011775 arteriosclerosis disease Diseases 0.000 description 1
229960005261 aspartic acid Drugs 0.000 description 1
230000001363 autoimmune Effects 0.000 description 1
230000031018 biological processes and functions Effects 0.000 description 1
229910002092 carbon dioxide Inorganic materials 0.000 description 1
239000001569 carbon dioxide Substances 0.000 description 1
229960003077 cycloserine Drugs 0.000 description 1
230000003247 decreasing effect Effects 0.000 description 1
230000007812 deficiency Effects 0.000 description 1
YSMODUONRAFBET-UHFFFAOYSA-N delta-DL-hydroxylysine Natural products NCC(O)CCC(N)C(O)=O YSMODUONRAFBET-UHFFFAOYSA-N 0.000 description 1
238000011161 development Methods 0.000 description 1
230000018109 developmental process Effects 0.000 description 1
239000012895 dilution Substances 0.000 description 1
238000010790 dilution Methods 0.000 description 1
LOKCTEFSRHRXRJ-UHFFFAOYSA-I dipotassium trisodium dihydrogen phosphate hydrogen phosphate dichloride Chemical compound P(=O)(O)(O)[O-].[K+].P(=O)(O)([O-])[O-].[Na+].[Na+].[Cl-].[K+].[Cl-].[Na+] LOKCTEFSRHRXRJ-UHFFFAOYSA-I 0.000 description 1
201000010099 disease Diseases 0.000 description 1
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
PMMYEEVYMWASQN-UHFFFAOYSA-N dl-hydroxyproline Natural products OC1C[NH2+]C(C([O-])=O)C1 PMMYEEVYMWASQN-UHFFFAOYSA-N 0.000 description 1
MBMBGCFOFBJSGT-SFGLVEFQSA-N docosa-4,7,10,13,16,19-hexaenoic acid Chemical compound CC\C=C\C\C=C\C\C=C\C\C=C\C\C=C\C\C=C\CCC(O)=O MBMBGCFOFBJSGT-SFGLVEFQSA-N 0.000 description 1
KAUVQQXNCKESLC-UHFFFAOYSA-N docosahexaenoic acid (DHA) Natural products COC(=O)C(C)NOCC1=CC=CC=C1 KAUVQQXNCKESLC-UHFFFAOYSA-N 0.000 description 1
239000008298 dragée Substances 0.000 description 1
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YSMODUONRAFBET-UHNVWZDZSA-N erythro-5-hydroxy-L-lysine Chemical compound NC[C@H](O)CC[C@H](N)C(O)=O YSMODUONRAFBET-UHNVWZDZSA-N 0.000 description 1
239000013505 freshwater Substances 0.000 description 1
BTCSSZJGUNDROE-UHFFFAOYSA-N gamma-aminobutyric acid Chemical compound NCCCC(O)=O BTCSSZJGUNDROE-UHFFFAOYSA-N 0.000 description 1
229920000159 gelatin Polymers 0.000 description 1
235000019322 gelatine Nutrition 0.000 description 1
210000004392 genitalia Anatomy 0.000 description 1
239000011521 glass Substances 0.000 description 1
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239000008240 homogeneous mixture Substances 0.000 description 1
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230000028996 humoral immune response Effects 0.000 description 1
QJHBJHUKURJDLG-UHFFFAOYSA-N hydroxy-L-lysine Natural products NCCCCC(NO)C(O)=O QJHBJHUKURJDLG-UHFFFAOYSA-N 0.000 description 1
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239000003226 mitogen Substances 0.000 description 1
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235000019515 salmon Nutrition 0.000 description 1
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235000019512 sardine Nutrition 0.000 description 1
229960001153 serine Drugs 0.000 description 1
239000011734 sodium Substances 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
239000011780 sodium chloride Substances 0.000 description 1
RPACBEVZENYWOL-XFULWGLBSA-M sodium;(2r)-2-[6-(4-chlorophenoxy)hexyl]oxirane-2-carboxylate Chemical compound [Na+].C=1C=C(Cl)C=CC=1OCCCCCC[C@]1(C(=O)[O-])CO1 RPACBEVZENYWOL-XFULWGLBSA-M 0.000 description 1
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230000001988 toxicity Effects 0.000 description 1
231100000419 toxicity Toxicity 0.000 description 1
FGMPLJWBKKVCDB-UHFFFAOYSA-N trans-L-hydroxy-proline Natural products ON1CCCC1C(O)=O FGMPLJWBKKVCDB-UHFFFAOYSA-N 0.000 description 1
230000009466 transformation Effects 0.000 description 1
210000004881 tumor cell Anatomy 0.000 description 1
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241001515965 unidentified phage Species 0.000 description 1
241001430294 unidentified retrovirus Species 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
- A61K31/185—Acids; Anhydrides, halides or salts thereof, e.g. sulfur acids, imidic, hydrazonic or hydroximic acids
- A61K31/19—Carboxylic acids, e.g. valproic acid
- A61K31/20—Carboxylic acids, e.g. valproic acid having a carboxyl group bound to a chain of seven or more carbon atoms, e.g. stearic, palmitic, arachidic acids
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/12—Antivirals
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/02—Immunomodulators
- A61P37/04—Immunostimulants

Landscapes

Health & Medical Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
Veterinary Medicine (AREA)
Pharmacology & Pharmacy (AREA)
Chemical & Material Sciences (AREA)
Public Health (AREA)
General Health & Medical Sciences (AREA)
Medicinal Chemistry (AREA)
Animal Behavior & Ethology (AREA)
Immunology (AREA)
General Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Chemical Kinetics & Catalysis (AREA)
Epidemiology (AREA)
Communicable Diseases (AREA)
Virology (AREA)
Oncology (AREA)
Engineering & Computer Science (AREA)
Bioinformatics & Cheminformatics (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)

CA000593270A 1988-03-09 1989-03-09 Compositions pharmaceutiques antivirales et procede de preparation Expired - Fee Related CA1334576C (fr)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
HU1132/88		1988-03-09
HU881132A HU209973B (en)	1988-03-09	1988-03-09	Process for production of antiviral and immunstimular pharmaceutical composition

Publications (1)

Publication Number	Publication Date
CA1334576C true CA1334576C (fr)	1995-02-28

Family

ID=10952974

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA000593270A Expired - Fee Related CA1334576C (fr)	1988-03-09	1989-03-09	Compositions pharmaceutiques antivirales et procede de preparation

Country Status (14)

Country	Link
JP (1)	JPH01316316A (fr)
KR (1)	KR890014103A (fr)
BE (1)	BE1002890A3 (fr)
CA (1)	CA1334576C (fr)
CH (1)	CH678918A5 (fr)
DE (1)	DE3907649C2 (fr)
FI (1)	FI94591C (fr)
FR (1)	FR2628324B1 (fr)
GB (1)	GB2216418B (fr)
HU (1)	HU209973B (fr)
IT (1)	IT1229562B (fr)
LU (1)	LU87471A1 (fr)
NL (1)	NL8900574A (fr)
SE (1)	SE8900828L (fr)

Families Citing this family (21)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
HU210122B (en) *	1988-03-23	1995-02-28	Biorex Kutato Fejlesztoe Kft	Process for production of composition against thromboembolytic conditions of circulating system and heart
JPH04279523A (ja) *	1991-01-11	1992-10-05	Nisshin Flour Milling Co Ltd	免疫賦活油脂加工品
GB9304746D0 (en) *	1993-03-09	1993-04-28	Scotia Holdings Plc	Treatment of viral infections
CA2159116A1 (fr) *	1993-03-26	1994-10-13	Constantin Romulus Dinu	Composition pharmaceutique servant a la lutte contre certains virus et a la lutte contre des maladies auto-immunes, et methode d'obtention
GB9318611D0 (en) *	1993-09-08	1993-10-27	Sandoz Nutrition Ltd	Improvements in or relating to organic compounds
US5767156A (en) *	1993-10-06	1998-06-16	Peptide Technology Limited	Polyunsaturated fatty acids and uses thereof
IT1264987B1 (it) *	1993-12-14	1996-10-17	Prospa Bv	Sali di un acido grasso poliinsaturo e formulazioni farmaceutiche che li contengono
AUPM906594A0 (en) *	1994-10-26	1994-11-17	Peptide Technology Limited	Synthetic polyunsaturated fatty acid analogues
DE19503993A1 (de) *	1995-02-08	1996-08-14	Johann Friedrich Dr Med Desaga	Verwendung eines Produktes zur enteralen Versorgung mit Lebensmittelinhaltsstoffen oder Arzneimittelinhaltsstoffen
US5639858A (en) *	1995-03-22	1997-06-17	Tularik, Inc.	Human signal transducer and binding assays
WO1996030381A1 (fr) *	1995-03-28	1996-10-03	Novo Nordisk A/S	Agents immunodepresseurs
HU227588B1 (hu)	2004-12-03	2011-09-28	Sinnex Mueszaki Fejlesztoe Es Tanacsado Kft	Többszörösen telítetlen zsírsavak észtereit tartalmazó vírusellenes és immunstimuláns gyógyászati készítmény
BRPI0820802A2 (pt) *	2007-12-17	2015-06-16	Univ Florida	Materiais e métodos para tratamento de proliferação vascular ocular patológica
FR3031451B1 (fr) *	2015-01-13	2018-03-23	Greentech	Sel d'un triglyceride, preparation et utilisations
PL3463310T3 (pl) *	2016-05-25	2023-12-04	Evonik Operations Gmbh	Tabletki o wysokiej zawartości składników aktywnych soli aminokwasowych kwasów tłuszczowych omega-3
EP3248467A1 (fr) *	2016-05-25	2017-11-29	Evonik Technochemie GmbH	Procede de production d'une composition contenant des sels lysine-l-acides gras-omega 3
WO2019008101A1 (fr)	2017-07-06	2019-01-10	Evonik Technochemie Gmbh	Forme posologique solide à enrobage entérique comprenant des sels d'acides aminés d'acides gras oméga-3
KR102628351B1 (ko)	2017-08-15	2024-01-25	에보니크 오퍼레이션즈 게엠베하	오메가-3 지방산 아미노산 염의 높은 활성 성분 함량을 갖는 정제
KR102977459B1 (ko)	2019-08-08	2026-06-16	에보니크 오퍼레이션즈 게엠베하	다중불포화 지방산 염의 제조를 위한 다운스트림 공정
US20220287345A1 (en)	2019-08-08	2022-09-15	Evonik Operations Gmbh	Solubility enhancement of poorly soluble actives
DE102022003441A1 (de)	2022-09-17	2024-03-28	Jutta Ibrahim	Nahrungsergänzungsmittel Omega3 und essentielle Aminosäure(n)

Family Cites Families (10)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
GB1256162A (en) *	1968-08-16	1971-12-08	Braun Fa B	Improvements in and relating to liquid products for intravenous administration
FR2215212B1 (fr) *	1973-01-18	1976-03-05	Seperic Ch
FR2508797B1 (fr) *	1981-07-03	1986-03-14	Charles Chany	Medicament comprenant le produit de la reaction d'un acide carboxylique en c1 a c6 sur un amino-acide basique
GB2118437B (en) *	1982-03-01	1984-12-12	Efamol Ltd	Composition for treating alcoholism
US4513008A (en) *	1982-07-30	1985-04-23	The Vinoxen Company, Inc.	Virucidal compositions and therapy
DE3229956A1 (de) *	1982-08-12	1984-02-16	Erichsen, Friedrich Karl, Dr., 2351 Schillsdorf	Arzneimittel mit cytostatischer wirkung
DE3514328C1 (de) *	1985-04-19	1986-09-11	Deutsches Krebsforschungszentrum Stiftung des öffentlichen Rechts, 6900 Heidelberg	Verwendung von L-Ornithin bei der selektiven Hemmung von cytotoxischen T-Lymphozyten-Effektorzellen
AU596880B2 (en) *	1986-09-17	1990-05-17	Clintec Nutrition Company	Liquid nutritional compositions
WO1988006035A1 (fr) *	1987-02-20	1988-08-25	Shriners Hospitals For Crippled Children	Acides gras omega-3 utilises dans le traitement de blessures traumatiques
DE3726299A1 (de) *	1987-06-26	1989-02-23	Dietl Hans	Fettemulsion zur intravenoesen anwendung

1988
- 1988-03-09 HU HU881132A patent/HU209973B/hu unknown
1989
- 1989-03-06 CH CH819/89A patent/CH678918A5/de not_active IP Right Cessation
- 1989-03-09 KR KR1019890002920A patent/KR890014103A/ko not_active Withdrawn
- 1989-03-09 SE SE8900828A patent/SE8900828L/xx not_active Application Discontinuation
- 1989-03-09 LU LU87471A patent/LU87471A1/fr unknown
- 1989-03-09 JP JP1055242A patent/JPH01316316A/ja active Pending
- 1989-03-09 DE DE3907649A patent/DE3907649C2/de not_active Expired - Fee Related
- 1989-03-09 NL NL8900574A patent/NL8900574A/nl not_active Application Discontinuation
- 1989-03-09 FR FR8903085A patent/FR2628324B1/fr not_active Expired - Fee Related
- 1989-03-09 IT IT8919704A patent/IT1229562B/it active
- 1989-03-09 CA CA000593270A patent/CA1334576C/fr not_active Expired - Fee Related
- 1989-03-09 BE BE8900254A patent/BE1002890A3/fr not_active IP Right Cessation
- 1989-03-09 GB GB8905385A patent/GB2216418B/en not_active Expired - Fee Related
- 1989-03-09 FI FI891145A patent/FI94591C/fi not_active IP Right Cessation

Also Published As

Publication number	Publication date
FR2628324B1 (fr)	1994-05-27
IT8919704A0 (it)	1989-03-09
FI891145L (fi)	1989-09-10
DE3907649C2 (de)	1996-07-11
GB2216418A (en)	1989-10-11
FI94591B (fi)	1995-06-30
FR2628324A1 (fr)	1989-09-15
IT1229562B (it)	1991-09-04
GB8905385D0 (en)	1989-04-19
DE3907649A1 (de)	1989-09-28
SE8900828L (sv)	1989-09-10
JPH01316316A (ja)	1989-12-21
BE1002890A3 (fr)	1991-07-16
FI94591C (fi)	1995-10-10
HUT60432A (en)	1992-09-28
LU87471A1 (fr)	1990-10-02
KR890014103A (ko)	1989-10-21
GB2216418B (en)	1991-12-11
SE8900828D0 (sv)	1989-03-09
NL8900574A (nl)	1989-10-02
FI891145A0 (fi)	1989-03-09
HU209973B (en)	1995-01-30
CH678918A5 (fr)	1991-11-29

Legal Events

Date	Code	Title	Description
2000-02-28	MKLA	Lapsed

Publication	Publication Date	Title
GB2216418A (en)	1989-10-11	Antiviral and immunostimulating compositions comprising amino acids and polyunsaturated higher fatty acids.
CA1339147C (fr)	1997-07-29	Composes de type sel; compositions pharmaceutiques a base de ces composes et methode pour les preparer
IL82459A (en)	1994-07-31	Stabilized pharmaceutical preparations containing polyunsaturated fatty acids and stimulating the synthesis of prostaglandins and hydroxy- and fatty acids in B systems
DE3684514D1 (de)	1992-04-30	Verwendung von penicillamin zur behandlung von immunmangelkrankheiten.
SE8406555D0 (sv)	1984-12-21	A process for obtaining ready-for-fertilization sexual products from sexually mature fish
JP4976307B2 (ja)	2012-07-18	新規な抗ウイルス性および免疫刺激性の医薬組成物
AU566974B2 (en)	1987-11-05	Pharmaceutical preparations containing a phospholipidan an oxicam derivative
Chen et al.	1977	Some immunological effects of penicillamine
EP0301474A3 (en)	1989-10-04	New cysteine derivatives having expectorant activity
US4845130A (en)	1989-07-04	Antihyperlipidemic amines
DE3627759A1 (de)	1987-03-19	Pharmazeutische zusammensetzung zum inaktivieren bakterieller endotoxine
MX174421B (es)	1994-05-16	Procedimiento para la preparacion de 4-arilcarbonil-1-[(4-morfolinil)-alquilo-inferior]-1h-indoles y producto obtenido
JPS58208225A (ja)	1983-12-03	抗腫瘍剤
PT86422A (fr)	1988-01-01	Procede de preparation de derives d:acide dibenzo]be"-oxepine-acetique et de compositions pharmaceutiques les contenant