MXPA02000315A - Profarmacos de pseudomicina. - Google Patents

Profarmacos de pseudomicina.

Info

Publication number: MXPA02000315A
Authority: MX; Mexico
Prior art keywords: carbon atoms; alkyl; hydrogen; c02ch3; alkoxy
Prior art date: 1999-07-15

Application number

MXPA02000315A

Other languages

English (en)

Spanish (es)

Inventor

Michael John Rodriguez

Original Assignee

Lilly Co Eli

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.)

1999-07-15

Filing date

2000-06-08

Publication date

2002-06-21

2000-06-08 Application filed by Lilly Co Eli filed Critical Lilly Co Eli

2002-06-21 Publication of MXPA02000315A publication Critical patent/MXPA02000315A/es

Links

239000000651 prodrug Substances 0.000 title claims abstract description 65
229940002612 prodrug Drugs 0.000 title claims abstract description 65
125000004432 carbon atom Chemical group C* 0.000 claims description 92
150000001875 compounds Chemical class 0.000 claims description 78
-1 -acetoacetate Chemical group 0.000 claims description 53
125000000217 alkyl group Chemical group 0.000 claims description 41
239000001257 hydrogen Substances 0.000 claims description 40
229910052739 hydrogen Inorganic materials 0.000 claims description 40
125000003545 alkoxy group Chemical group 0.000 claims description 28
125000003118 aryl group Chemical group 0.000 claims description 28
241001465754 Metazoa Species 0.000 claims description 21
238000002360 preparation method Methods 0.000 claims description 18
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 17
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 17
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 15
125000000753 cycloalkyl group Chemical group 0.000 claims description 13
239000003814 drug Substances 0.000 claims description 12
238000004519 manufacturing process Methods 0.000 claims description 12
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 12
125000003342 alkenyl group Chemical group 0.000 claims description 11
125000003282 alkyl amino group Chemical group 0.000 claims description 10
150000003839 salts Chemical class 0.000 claims description 10
239000012453 solvate Substances 0.000 claims description 10
206010017533 Fungal infection Diseases 0.000 claims description 9
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 9
208000031888 Mycoses Diseases 0.000 claims description 9
229910052799 carbon Inorganic materials 0.000 claims description 7
150000002148 esters Chemical class 0.000 claims description 7
229910052736 halogen Inorganic materials 0.000 claims description 7
150000002367 halogens Chemical class 0.000 claims description 7
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 7
150000001413 amino acids Chemical class 0.000 claims description 6
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 6
RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Substances C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims description 5
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 5
239000008194 pharmaceutical composition Substances 0.000 claims description 4
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 3
125000004183 alkoxy alkyl group Chemical group 0.000 claims description 3
125000004103 aminoalkyl group Chemical group 0.000 claims description 3
125000003710 aryl alkyl group Chemical group 0.000 claims description 3
239000003085 diluting agent Substances 0.000 claims description 3
125000004446 heteroarylalkyl group Chemical group 0.000 claims description 3
125000005113 hydroxyalkoxy group Chemical group 0.000 claims description 3
239000000546 pharmaceutical excipient Substances 0.000 claims description 3
125000004055 thiomethyl group Chemical group [H]SC([H])([H])* 0.000 claims description 3
239000000872 buffer Substances 0.000 claims description 2
239000003937 drug carrier Substances 0.000 claims description 2
CBOIHMRHGLHBPB-UHFFFAOYSA-N hydroxymethyl Chemical compound O[CH2] CBOIHMRHGLHBPB-UHFFFAOYSA-N 0.000 claims description 2
150000002431 hydrogen Chemical class 0.000 claims 16
125000005599 alkyl carboxylate group Chemical group 0.000 claims 4
125000005907 alkyl ester group Chemical group 0.000 claims 2
ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims 2
125000002768 hydroxyalkyl group Chemical group 0.000 claims 2
235000010290 biphenyl Nutrition 0.000 claims 1
239000004305 biphenyl Substances 0.000 claims 1
230000009897 systematic effect Effects 0.000 claims 1
230000000843 anti-fungal effect Effects 0.000 abstract description 11
230000002411 adverse Effects 0.000 abstract description 7
230000000694 effects Effects 0.000 abstract description 7
238000000034 method Methods 0.000 description 40
239000000203 mixture Substances 0.000 description 32
241000589615 Pseudomonas syringae Species 0.000 description 29
238000006243 chemical reaction Methods 0.000 description 27
NYRWZRIVFVWNTD-SGRJACMKSA-N (2s)-2-[(3s,6s,9z,12s,15s,18s,21s,24r,27s)-18-(4-aminobutyl)-15,24-bis(2-aminoethyl)-21-(carboxymethyl)-3-[(1s)-2-chloro-1-hydroxyethyl]-9-ethylidene-12-[(1s)-1-hydroxyethyl]-27-[[(3r)-3-hydroxytetradecanoyl]amino]-2,5,8,11,14,17,20,23,26-nonaoxo-1-oxa-4, Chemical compound CCCCCCCCCCC[C@@H](O)CC(=O)N[C@H]1COC(=O)[C@H]([C@H](O)CCl)NC(=O)[C@H]([C@H](O)C(O)=O)NC(=O)\C(=C\C)NC(=O)[C@H]([C@H](C)O)NC(=O)[C@H](CCN)NC(=O)[C@H](CCCCN)NC(=O)[C@H](CC(O)=O)NC(=O)[C@@H](CCN)NC1=O NYRWZRIVFVWNTD-SGRJACMKSA-N 0.000 description 24
239000000243 solution Substances 0.000 description 24
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 23
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 22
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 21
108010033821 pseudomycin B Proteins 0.000 description 21
239000002253 acid Substances 0.000 description 20
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 19
239000000047 product Substances 0.000 description 18
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 17
KZSKIDBMTSZKLE-NDWYDANWSA-N (2s)-2-[(3s,6s,9e,12s,15r,18s,21s,24r,27s)-18-(4-aminobutyl)-15,24-bis(2-aminoethyl)-21-(carboxymethyl)-3-[(1s)-2-chloro-1-hydroxyethyl]-9-ethylidene-12-[(1s)-1-hydroxyethyl]-27-[[(3r)-3-hydroxyhexadecanoyl]amino]-2,5,8,11,14,17,20,23,26-nonaoxo-1-oxa-4,7 Chemical compound CCCCCCCCCCCCC[C@@H](O)CC(=O)N[C@H]1COC(=O)[C@H]([C@H](O)CCl)NC(=O)[C@H]([C@H](O)C(O)=O)NC(=O)\C(=C/C)NC(=O)[C@H]([C@H](C)O)NC(=O)[C@@H](CCN)NC(=O)[C@H](CCCCN)NC(=O)[C@H](CC(O)=O)NC(=O)[C@@H](CCN)NC1=O KZSKIDBMTSZKLE-NDWYDANWSA-N 0.000 description 16
230000015572 biosynthetic process Effects 0.000 description 16
210000003462 vein Anatomy 0.000 description 15
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 14
DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 12
239000002904 solvent Substances 0.000 description 12
241000222122 Candida albicans Species 0.000 description 11
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 11
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 10
125000006239 protecting group Chemical group 0.000 description 10
238000003756 stirring Methods 0.000 description 10
238000003786 synthesis reaction Methods 0.000 description 10
231100000419 toxicity Toxicity 0.000 description 10
230000001988 toxicity Effects 0.000 description 10
238000001727 in vivo Methods 0.000 description 9
125000003277 amino group Chemical group 0.000 description 8
235000019439 ethyl acetate Nutrition 0.000 description 8
239000002609 medium Substances 0.000 description 8
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 7
230000007794 irritation Effects 0.000 description 7
125000001424 substituent group Chemical group 0.000 description 7
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 6
238000005917 acylation reaction Methods 0.000 description 6
125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 6
229910052757 nitrogen Inorganic materials 0.000 description 6
KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 6
238000004007 reversed phase HPLC Methods 0.000 description 6
230000009885 systemic effect Effects 0.000 description 6
XDPWWEOIDYYUDN-HCEIJDMSSA-N 2-[(9z)-18-(4-aminobutyl)-15,24-bis(2-aminoethyl)-21-(carboxymethyl)-3-(2-chloro-1-hydroxyethyl)-27-(3,4-dihydroxytetradecanoylamino)-9-ethylidene-12-(1-hydroxyethyl)-2,5,8,11,14,17,20,23,26-nonaoxo-1-oxa-4,7,10,13,16,19,22,25-octazacyclooctacos-6-yl]-2-h Chemical compound CCCCCCCCCCC(O)C(O)CC(=O)NC1COC(=O)C(C(O)CCl)NC(=O)C(C(O)C(O)=O)NC(=O)\C(=C\C)NC(=O)C(C(C)O)NC(=O)C(CCN)NC(=O)C(CCCCN)NC(=O)C(CC(O)=O)NC(=O)C(CCN)NC1=O XDPWWEOIDYYUDN-HCEIJDMSSA-N 0.000 description 5
206010007134 Candida infections Diseases 0.000 description 5
241000233866 Fungi Species 0.000 description 5
CKLJMWTZIZZHCS-REOHCLBHSA-N L-aspartic acid Chemical compound OC(=O)[C@@H](N)CC(O)=O CKLJMWTZIZZHCS-REOHCLBHSA-N 0.000 description 5
241001529936 Murinae Species 0.000 description 5
241000699670 Mus sp. Species 0.000 description 5
230000010933 acylation Effects 0.000 description 5
235000001014 amino acid Nutrition 0.000 description 5
229940024606 amino acid Drugs 0.000 description 5
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 5
239000012267 brine Substances 0.000 description 5
201000003984 candidiasis Diseases 0.000 description 5
229940079593 drug Drugs 0.000 description 5
238000004108 freeze drying Methods 0.000 description 5
238000004128 high performance liquid chromatography Methods 0.000 description 5
239000000463 material Substances 0.000 description 5
239000012044 organic layer Substances 0.000 description 5
239000001301 oxygen Substances 0.000 description 5
229910052760 oxygen Inorganic materials 0.000 description 5
108090000765 processed proteins & peptides Proteins 0.000 description 5
108010033876 pseudomycin A Proteins 0.000 description 5
238000000746 purification Methods 0.000 description 5
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 5
238000005160 1H NMR spectroscopy Methods 0.000 description 4
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 4
DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 description 4
239000012317 TBTU Substances 0.000 description 4
CLZISMQKJZCZDN-UHFFFAOYSA-N [benzotriazol-1-yloxy(dimethylamino)methylidene]-dimethylazanium Chemical compound C1=CC=C2N(OC(N(C)C)=[N+](C)C)N=NC2=C1 CLZISMQKJZCZDN-UHFFFAOYSA-N 0.000 description 4
239000004480 active ingredient Substances 0.000 description 4
125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 description 4
125000002843 carboxylic acid group Chemical group 0.000 description 4
239000003795 chemical substances by application Substances 0.000 description 4
239000007822 coupling agent Substances 0.000 description 4
230000020176 deacylation Effects 0.000 description 4
238000005947 deacylation reaction Methods 0.000 description 4
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 4
238000009472 formulation Methods 0.000 description 4
238000005984 hydrogenation reaction Methods 0.000 description 4
208000015181 infectious disease Diseases 0.000 description 4
230000002401 inhibitory effect Effects 0.000 description 4
229930014626 natural product Natural products 0.000 description 4
239000003921 oil Substances 0.000 description 4
239000011541 reaction mixture Substances 0.000 description 4
238000010898 silica gel chromatography Methods 0.000 description 4
238000012360 testing method Methods 0.000 description 4
VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 4
241001225321 Aspergillus fumigatus Species 0.000 description 3
241000221204 Cryptococcus neoformans Species 0.000 description 3
241000196324 Embryophyta Species 0.000 description 3
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 3
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
150000007513 acids Chemical class 0.000 description 3
125000001931 aliphatic group Chemical group 0.000 description 3
150000001408 amides Chemical class 0.000 description 3
235000003704 aspartic acid Nutrition 0.000 description 3
OQFSQFPPLPISGP-UHFFFAOYSA-N beta-carboxyaspartic acid Natural products OC(=O)C(N)C(C(O)=O)C(O)=O OQFSQFPPLPISGP-UHFFFAOYSA-N 0.000 description 3
229940095731 candida albicans Drugs 0.000 description 3
239000003054 catalyst Substances 0.000 description 3
125000004122 cyclic group Chemical group 0.000 description 3
230000007613 environmental effect Effects 0.000 description 3
230000032050 esterification Effects 0.000 description 3
238000005886 esterification reaction Methods 0.000 description 3
230000002538 fungal effect Effects 0.000 description 3
239000001963 growth medium Substances 0.000 description 3
230000005764 inhibitory process Effects 0.000 description 3
KDXKERNSBIXSRK-UHFFFAOYSA-N lysine Chemical compound NCCCCC(N)C(O)=O KDXKERNSBIXSRK-UHFFFAOYSA-N 0.000 description 3
231100000350 mutagenesis Toxicity 0.000 description 3
238000002703 mutagenesis Methods 0.000 description 3
239000003471 mutagenic agent Substances 0.000 description 3
UYWQUFXKFGHYNT-UHFFFAOYSA-N phenylmethyl ester of formic acid Natural products O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 0.000 description 3
239000000843 powder Substances 0.000 description 3
229910052938 sodium sulfate Inorganic materials 0.000 description 3
235000011152 sodium sulphate Nutrition 0.000 description 3
239000007787 solid Substances 0.000 description 3
241000894007 species Species 0.000 description 3
LMDZBCPBFSXMTL-UHFFFAOYSA-N 1-Ethyl-3-(3-dimethylaminopropyl)carbodiimide Substances CCN=C=NCCCN(C)C LMDZBCPBFSXMTL-UHFFFAOYSA-N 0.000 description 2
OGNSCSPNOLGXSM-UHFFFAOYSA-N 2,4-diaminobutyric acid Chemical compound NCCC(N)C(O)=O OGNSCSPNOLGXSM-UHFFFAOYSA-N 0.000 description 2
AAPRNHKWNGDTOT-DVRVPOOOSA-N 2-[(3s)-3-(aminomethyl)piperidine-1-carbonyl]-n-[1-(cyclononen-1-ylmethyl)piperidin-4-yl]-9h-xanthene-9-carboxamide Chemical compound C1[C@H](CN)CCCN1C(=O)C1=CC=C(OC=2C(=CC=CC=2)C2C(=O)NC3CCN(CC=4CCCCCCCC=4)CC3)C2=C1 AAPRNHKWNGDTOT-DVRVPOOOSA-N 0.000 description 2
FPQQSJJWHUJYPU-UHFFFAOYSA-N 3-(dimethylamino)propyliminomethylidene-ethylazanium;chloride Chemical compound Cl.CCN=C=NCCCN(C)C FPQQSJJWHUJYPU-UHFFFAOYSA-N 0.000 description 2
XVMSFILGAMDHEY-UHFFFAOYSA-N 6-(4-aminophenyl)sulfonylpyridin-3-amine Chemical compound C1=CC(N)=CC=C1S(=O)(=O)C1=CC=C(N)C=N1 XVMSFILGAMDHEY-UHFFFAOYSA-N 0.000 description 2
VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 2
241000894006 Bacteria Species 0.000 description 2
241000283690 Bos taurus Species 0.000 description 2
WSNMPAVSZJSIMT-UHFFFAOYSA-N COc1c(C)c2COC(=O)c2c(O)c1CC(O)C1(C)CCC(=O)O1 Chemical compound COc1c(C)c2COC(=O)c2c(O)c1CC(O)C1(C)CCC(=O)O1 WSNMPAVSZJSIMT-UHFFFAOYSA-N 0.000 description 2
241000222120 Candida <Saccharomycetales> Species 0.000 description 2
241000282472 Canis lupus familiaris Species 0.000 description 2
KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 description 2
239000004215 Carbon black (E152) Substances 0.000 description 2
108010069514 Cyclic Peptides Proteins 0.000 description 2
102000001189 Cyclic Peptides Human genes 0.000 description 2
HTJDQJBWANPRPF-UHFFFAOYSA-N Cyclopropylamine Chemical compound NC1CC1 HTJDQJBWANPRPF-UHFFFAOYSA-N 0.000 description 2
241000283086 Equidae Species 0.000 description 2
PLUBXMRUUVWRLT-UHFFFAOYSA-N Ethyl methanesulfonate Chemical compound CCOS(C)(=O)=O PLUBXMRUUVWRLT-UHFFFAOYSA-N 0.000 description 2
241000282326 Felis catus Species 0.000 description 2
239000004471 Glycine Substances 0.000 description 2
229910004373 HOAc Inorganic materials 0.000 description 2
125000002842 L-seryl group Chemical group O=C([*])[C@](N([H])[H])([H])C([H])([H])O[H] 0.000 description 2
239000004472 Lysine Substances 0.000 description 2
IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 description 2
238000005481 NMR spectroscopy Methods 0.000 description 2
UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
241001494479 Pecora Species 0.000 description 2
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical class OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
241000282887 Suidae Species 0.000 description 2
LSNNMFCWUKXFEE-UHFFFAOYSA-N Sulfurous acid Chemical class OS(O)=O LSNNMFCWUKXFEE-UHFFFAOYSA-N 0.000 description 2
DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 2
230000009471 action Effects 0.000 description 2
230000003213 activating effect Effects 0.000 description 2
125000002252 acyl group Chemical group 0.000 description 2
230000009435 amidation Effects 0.000 description 2
238000007112 amidation reaction Methods 0.000 description 2
125000003368 amide group Chemical group 0.000 description 2
239000000908 ammonium hydroxide Substances 0.000 description 2
MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 2
230000001857 anti-mycotic effect Effects 0.000 description 2
229940121375 antifungal agent Drugs 0.000 description 2
239000003429 antifungal agent Substances 0.000 description 2
239000002543 antimycotic Substances 0.000 description 2
239000003125 aqueous solvent Substances 0.000 description 2
125000004104 aryloxy group Chemical group 0.000 description 2
229940091771 aspergillus fumigatus Drugs 0.000 description 2
WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 description 2
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
229950005499 carbon tetrachloride Drugs 0.000 description 2
239000010779 crude oil Substances 0.000 description 2
239000012043 crude product Substances 0.000 description 2
125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 2
HGCIXCUEYOPUTN-UHFFFAOYSA-N cyclohexene Chemical compound C1CCC=CC1 HGCIXCUEYOPUTN-UHFFFAOYSA-N 0.000 description 2
125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 2
125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 2
230000006378 damage Effects 0.000 description 2
238000010511 deprotection reaction Methods 0.000 description 2
238000011161 development Methods 0.000 description 2
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239000000706 filtrate Substances 0.000 description 2
238000001914 filtration Methods 0.000 description 2
235000013305 food Nutrition 0.000 description 2
239000007789 gas Substances 0.000 description 2
239000008103 glucose Substances 0.000 description 2
150000004820 halides Chemical class 0.000 description 2
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NPZTUJOABDZTLV-UHFFFAOYSA-N hydroxybenzotriazole Substances O=C1C=CC=C2NNN=C12 NPZTUJOABDZTLV-UHFFFAOYSA-N 0.000 description 2
239000007924 injection Substances 0.000 description 2
238000002347 injection Methods 0.000 description 2
239000013067 intermediate product Substances 0.000 description 2
125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 2
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
125000005647 linker group Chemical group 0.000 description 2
150000002632 lipids Chemical class 0.000 description 2
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- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K7/00—Peptides having 5 to 20 amino acids in a fully defined sequence; Derivatives thereof
- C07K7/04—Linear peptides containing only normal peptide links
- C07K7/06—Linear peptides containing only normal peptide links having 5 to 11 amino acids
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
- 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
- A61P31/04—Antibacterial agents
- 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
- A61P31/10—Antimycotics
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K38/00—Medicinal preparations containing peptides

Landscapes

Health & Medical Sciences (AREA)
Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
General Health & Medical Sciences (AREA)
Medicinal Chemistry (AREA)
Life Sciences & Earth Sciences (AREA)
Veterinary Medicine (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Pharmacology & Pharmacy (AREA)
General Chemical & Material Sciences (AREA)
Animal Behavior & Ethology (AREA)
Public Health (AREA)
Chemical Kinetics & Catalysis (AREA)
Oncology (AREA)
Communicable Diseases (AREA)
Biochemistry (AREA)
Biophysics (AREA)
Genetics & Genomics (AREA)
Molecular Biology (AREA)
Proteomics, Peptides & Aminoacids (AREA)
Engineering & Computer Science (AREA)
Bioinformatics & Cheminformatics (AREA)
Dermatology (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Peptides Or Proteins (AREA)

MXPA02000315A 1999-07-15 2000-06-08 Profarmacos de pseudomicina. MXPA02000315A (es)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US14384099P	1999-07-15	1999-07-15
PCT/US2000/015016 WO2001005813A1 (en)	1999-07-15	2000-06-08	Pseudomycin prodrugs

Publications (1)

Publication Number	Publication Date
MXPA02000315A true MXPA02000315A (es)	2002-06-21

Family

ID=22505903

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
MXPA02000315A MXPA02000315A (es)	1999-07-15	2000-06-08	Profarmacos de pseudomicina.

Country Status (11)

Country	Link
EP (1)	EP1198470A1 (no)
JP (1)	JP2003505396A (no)
CN (1)	CN1373770A (no)
AU (1)	AU5310500A (no)
BR (1)	BR0013153A (no)
CA (1)	CA2379058A1 (no)
EA (1)	EA200200161A1 (no)
HU (1)	HUP0202223A3 (no)
MX (1)	MXPA02000315A (no)
NO (1)	NO20020192L (no)
WO (1)	WO2001005813A1 (no)

Families Citing this family (10)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US6818787B2 (en)	2001-06-11	2004-11-16	Xenoport, Inc.	Prodrugs of GABA analogs, compositions and uses thereof
US8048917B2 (en)	2005-04-06	2011-11-01	Xenoport, Inc.	Prodrugs of GABA analogs, compositions and uses thereof
US7186855B2 (en)	2001-06-11	2007-03-06	Xenoport, Inc.	Prodrugs of GABA analogs, compositions and uses thereof
US7232924B2 (en)	2001-06-11	2007-06-19	Xenoport, Inc.	Methods for synthesis of acyloxyalkyl derivatives of GABA analogs
WO2005019163A2 (en) *	2003-08-20	2005-03-03	Xenoport, Inc.	Acyloxyalkyl carbamate prodrugs, methods of synthesis and use
CN102702065A (zh)	2003-12-30	2012-10-03	什诺波特有限公司	酰氧基烃基氨基甲酸酯前药及其中间体的合成
CN101486668B (zh) *	2003-12-30	2014-07-02	什诺波特有限公司	酰氧基烃基氨基甲酸酯前药及其中间体的合成
ATE469880T1 (de)	2005-06-20	2010-06-15	Xenoport Inc	Acyloxyalkylcarbamat-prodrugs von tranexansäure und anwendung
TW200820963A (en)	2006-07-28	2008-05-16	Xenoport Inc	Acyloxyalkyl carbamate prodrugs of α-amino acids, methods of synthesis and use
US7989641B2 (en)	2008-08-07	2011-08-02	Xenoport, Inc.	Methods of synthesizing N-hydroxysuccinimidyl carbonates

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US5576298A (en) *	1992-11-30	1996-11-19	Research And Development Institute, Inc. At Montana State University	Peptides from pseudomonas syringae possessing broad-spectrum antibiotic activity

2000
- 2000-06-08 CN CN00810331A patent/CN1373770A/zh active Pending
- 2000-06-08 EA EA200200161A patent/EA200200161A1/ru unknown
- 2000-06-08 CA CA002379058A patent/CA2379058A1/en not_active Abandoned
- 2000-06-08 AU AU53105/00A patent/AU5310500A/en not_active Abandoned
- 2000-06-08 BR BR0013153-9A patent/BR0013153A/pt not_active Application Discontinuation
- 2000-06-08 WO PCT/US2000/015016 patent/WO2001005813A1/en not_active Ceased
- 2000-06-08 HU HU0202223A patent/HUP0202223A3/hu unknown
- 2000-06-08 EP EP00938005A patent/EP1198470A1/en not_active Withdrawn
- 2000-06-08 JP JP2001511470A patent/JP2003505396A/ja not_active Withdrawn
- 2000-06-08 MX MXPA02000315A patent/MXPA02000315A/es unknown
2002
- 2002-01-14 NO NO20020192A patent/NO20020192L/no not_active Application Discontinuation

Also Published As

Publication number	Publication date
JP2003505396A (ja)	2003-02-12
CA2379058A1 (en)	2001-01-25
AU5310500A (en)	2001-02-05
HUP0202223A2 (en)	2002-10-28
EP1198470A1 (en)	2002-04-24
NO20020192D0 (no)	2002-01-14
HUP0202223A3 (en)	2002-11-28
CN1373770A (zh)	2002-10-09
EA200200161A1 (ru)	2002-06-27
NO20020192L (no)	2002-03-14
WO2001005813A1 (en)	2001-01-25
BR0013153A (pt)	2002-04-02

Publication	Publication Date	Title
KR20110119699A (ko)	2011-11-02	데옥시악타가르딘 유도체
MXPA02000315A (es)	2002-06-21	Profarmacos de pseudomicina.
CN101522705B (zh)	2013-10-02	来自actinomadura namibiensis的抗菌和抗病毒肽
US7098186B2 (en)	2006-08-29	Depsipeptide compound
CA2379851A1 (en)	2001-01-25	Pseudomycin n-acyl side-chain analogs
MXPA02005791A (es)	2002-09-30	Profarmacos de fosfato de pseudomicina.
DE102004051023A1 (de)	2006-05-04	Desoxo-Nonadepsipeptide
JP2004524318A (ja)	2004-08-12	エチノカンジン誘導体およびその医薬組成物および医薬としての用途
US20030008814A1 (en)	2003-01-09	Pseudomycin phosphate prodrugs
US6331521B1 (en)	2001-12-18	Echinocandine derivatives with antimicrobial activity
MXPA02000458A (es)	2002-07-02	Proceso para la desacilacion de lipodepsipeptidos.
MXPA02000320A (es)	2002-06-21	Compuestos de pseudomicina modificados en los grupos amina.
MXPA02000312A (es)	2002-06-21	Analogos de amida y ester de pseudomicina.
US6399567B1 (en)	2002-06-04	Cyclic hexapeptides having antibiotic activity
WO1998004584A1 (en)	1998-02-05	Cyclic decapeptide antibiotics
ES2304954T3 (es)	2008-11-01	Analogos de pseudomicina.
HK1135708B (en)	2014-06-27	Antibacterial and antiviral peptides from actinomadura namibiensis