DK3055030T3 - AMPHOTERICIN B DERIVATIVES WITH IMPROVED THERAPEUTIC INDEX - Google Patents

Info

Publication number

DK3055030T3

DK3055030T3 DK14853012.4T DK14853012T DK3055030T3 DK 3055030 T3 DK3055030 T3 DK 3055030T3 DK 14853012 T DK14853012 T DK 14853012T DK 3055030 T3 DK3055030 T3 DK 3055030T3

Authority

DK

Denmark

Prior art keywords

amb

compound

synthesis

vol

derivatives

Prior art date

2013-10-07

Links

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• Global Dossier
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• APKFDSVGJQXUKY-INPOYWNPSA-N amphotericin B Chemical class O[C@H]1[C@@H](N)[C@H](O)[C@@H](C)O[C@H]1O[C@H]1/C=C/C=C/C=C/C=C/C=C/C=C/C=C/[C@H](C)[C@@H](O)[C@@H](C)[C@H](C)OC(=O)C[C@H](O)C[C@H](O)CC[C@@H](O)[C@H](O)C[C@H](O)C[C@](O)(C[C@H](O)[C@H]2C(O)=O)O[C@H]2C1 APKFDSVGJQXUKY-INPOYWNPSA-N 0.000 title abstract description 104
• 231100001274 therapeutic index Toxicity 0.000 title description 7
• APKFDSVGJQXUKY-KKGHZKTASA-N Amphotericin-B Natural products O[C@H]1[C@@H](N)[C@H](O)[C@@H](C)O[C@H]1O[C@H]1C=CC=CC=CC=CC=CC=CC=C[C@H](C)[C@@H](O)[C@@H](C)[C@H](C)OC(=O)C[C@H](O)C[C@H](O)CC[C@@H](O)[C@H](O)C[C@H](O)C[C@](O)(C[C@H](O)[C@H]2C(O)=O)O[C@H]2C1 APKFDSVGJQXUKY-KKGHZKTASA-N 0.000 claims abstract description 95
• 229960003942 amphotericin b Drugs 0.000 claims abstract description 95
• 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 25
• 238000000034 method Methods 0.000 claims abstract description 18
• 150000003672 ureas Chemical class 0.000 claims abstract description 15
• 150000001875 compounds Chemical class 0.000 claims description 85
• 150000003839 salts Chemical class 0.000 claims description 47
• 206010017533 Fungal infection Diseases 0.000 claims description 23
• 238000004519 manufacturing process Methods 0.000 claims description 17
• 241000233866 Fungi Species 0.000 claims description 16
• 208000031888 Mycoses Diseases 0.000 claims description 15
• 239000001257 hydrogen Substances 0.000 claims description 14
• 229910052739 hydrogen Inorganic materials 0.000 claims description 14
• 230000002401 inhibitory effect Effects 0.000 claims description 11
• 235000013877 carbamide Nutrition 0.000 claims description 9
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 8
• 239000003937 drug carrier Substances 0.000 claims description 7
• 238000011282 treatment Methods 0.000 claims description 7
• 230000012010 growth Effects 0.000 claims description 6
• 230000009466 transformation Effects 0.000 claims description 6
• 229940125904 compound 1 Drugs 0.000 claims description 4
• 239000006186 oral dosage form Substances 0.000 claims description 4
• 239000006207 intravenous dosage form Substances 0.000 claims description 3
• 230000000843 anti-fungal effect Effects 0.000 abstract description 10
• 231100000419 toxicity Toxicity 0.000 abstract description 8
• 230000001988 toxicity Effects 0.000 abstract description 8
• 230000002829 reductive effect Effects 0.000 abstract description 6
• DTSSDPFTHGBSDX-KVTDHHQDSA-N mycosamine Chemical compound C[C@@H](O)[C@@H](O)[C@H](N)[C@H](O)C=O DTSSDPFTHGBSDX-KVTDHHQDSA-N 0.000 abstract description 5
• 230000004048 modification Effects 0.000 abstract description 4
• 238000012986 modification Methods 0.000 abstract description 4
• 230000000717 retained effect Effects 0.000 abstract 1
• 230000015572 biosynthetic process Effects 0.000 description 87
• 238000003786 synthesis reaction Methods 0.000 description 73
• -1 amino AmB derivatives Chemical class 0.000 description 59
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• 238000009472 formulation Methods 0.000 description 41
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 38
• 239000003814 drug Substances 0.000 description 37
• HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 33
• ZADPBFCGQRWHPN-UHFFFAOYSA-N boronic acid Chemical compound OBO ZADPBFCGQRWHPN-UHFFFAOYSA-N 0.000 description 30
• 240000004808 Saccharomyces cerevisiae Species 0.000 description 27
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• 241001139947 Mida Species 0.000 description 24
• 230000009467 reduction Effects 0.000 description 23
• 238000006722 reduction reaction Methods 0.000 description 23
• WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 21
• 238000010511 deprotection reaction Methods 0.000 description 21
• HVYWMOMLDIMFJA-DPAQBDIFSA-N cholesterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2 HVYWMOMLDIMFJA-DPAQBDIFSA-N 0.000 description 20
• 239000000126 substance Substances 0.000 description 20
• 238000006257 total synthesis reaction Methods 0.000 description 20
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• 150000002576 ketones Chemical class 0.000 description 18
• 125000000217 alkyl group Chemical group 0.000 description 17
• 229910052799 carbon Inorganic materials 0.000 description 17
• KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 16
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• 230000003647 oxidation Effects 0.000 description 16
• 238000007254 oxidation reaction Methods 0.000 description 16
• YWWDBCBWQNCYNR-UHFFFAOYSA-N trimethylphosphine Chemical compound CP(C)C YWWDBCBWQNCYNR-UHFFFAOYSA-N 0.000 description 16
• OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 15
• 230000008878 coupling Effects 0.000 description 15
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• 238000005859 coupling reaction Methods 0.000 description 15
• 230000001225 therapeutic effect Effects 0.000 description 15
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 15
• 238000006161 Suzuki-Miyaura coupling reaction Methods 0.000 description 14
• 150000001299 aldehydes Chemical class 0.000 description 14
• XXROGKLTLUQVRX-UHFFFAOYSA-N allyl alcohol Chemical compound OCC=C XXROGKLTLUQVRX-UHFFFAOYSA-N 0.000 description 14
• 239000002245 particle Substances 0.000 description 14
• 125000003118 aryl group Chemical group 0.000 description 13
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• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical group CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 12
• DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 12
• 239000012634 fragment Substances 0.000 description 12
• 238000006206 glycosylation reaction Methods 0.000 description 12
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• 239000000843 powder Substances 0.000 description 12
• 125000006239 protecting group Chemical group 0.000 description 12
• LWIHDJKSTIGBAC-UHFFFAOYSA-K tripotassium phosphate Chemical compound [K+].[K+].[K+].[O-]P([O-])([O-])=O LWIHDJKSTIGBAC-UHFFFAOYSA-K 0.000 description 12
• 229920002472 Starch Polymers 0.000 description 11
• 230000000694 effects Effects 0.000 description 11
• 150000007931 macrolactones Chemical class 0.000 description 11
• 239000000463 material Substances 0.000 description 11
• GRJJQCWNZGRKAU-UHFFFAOYSA-N pyridin-1-ium;fluoride Chemical compound F.C1=CC=NC=C1 GRJJQCWNZGRKAU-UHFFFAOYSA-N 0.000 description 11
• OILXMJHPFNGGTO-UHFFFAOYSA-N (22E)-(24xi)-24-methylcholesta-5,22-dien-3beta-ol Natural products C1C=C2CC(O)CCC2(C)C2C1C1CCC(C(C)C=CC(C)C(C)C)C1(C)CC2 OILXMJHPFNGGTO-UHFFFAOYSA-N 0.000 description 10
• RQOCXCFLRBRBCS-UHFFFAOYSA-N (22E)-cholesta-5,7,22-trien-3beta-ol Natural products C1C(O)CCC2(C)C(CCC3(C(C(C)C=CCC(C)C)CCC33)C)C3=CC=C21 RQOCXCFLRBRBCS-UHFFFAOYSA-N 0.000 description 10
• OQMZNAMGEHIHNN-UHFFFAOYSA-N 7-Dehydrostigmasterol Natural products C1C(O)CCC2(C)C(CCC3(C(C(C)C=CC(CC)C(C)C)CCC33)C)C3=CC=C21 OQMZNAMGEHIHNN-UHFFFAOYSA-N 0.000 description 10
• DNVPQKQSNYMLRS-NXVQYWJNSA-N Ergosterol Natural products CC(C)[C@@H](C)C=C[C@H](C)[C@H]1CC[C@H]2C3=CC=C4C[C@@H](O)CC[C@]4(C)[C@@H]3CC[C@]12C DNVPQKQSNYMLRS-NXVQYWJNSA-N 0.000 description 10
• 108010010803 Gelatin Proteins 0.000 description 10
• NIWUMFULEUZEOT-UHFFFAOYSA-N O=P1OOO1 Chemical compound O=P1OOO1 NIWUMFULEUZEOT-UHFFFAOYSA-N 0.000 description 10
• 235000012000 cholesterol Nutrition 0.000 description 10
• 238000005828 desilylation reaction Methods 0.000 description 10
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• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 10
• DNVPQKQSNYMLRS-SOWFXMKYSA-N ergosterol Chemical compound C1[C@@H](O)CC[C@]2(C)[C@H](CC[C@]3([C@H]([C@H](C)/C=C/[C@@H](C)C(C)C)CC[C@H]33)C)C3=CC=C21 DNVPQKQSNYMLRS-SOWFXMKYSA-N 0.000 description 10
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• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 10
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• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 8
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• 241000699670 Mus sp. Species 0.000 description 8
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