MXPA01008326A

MXPA01008326A -

Info

Publication number: MXPA01008326A
Authority: MX; Mexico
Prior art keywords: group; liposomal preparation; pharmaceutically acceptable; pipecolic acid; hydrogen atom
Prior art date: 2001-08-16

Application number

MXPA/A/2001/008326A

Other languages

English (en)

Spanish (es)

Filing date

2001-08-16

Publication date

2002-05-09

2001-08-16 Application filed filed Critical

2002-05-09 Publication of MXPA01008326A publication Critical patent/MXPA01008326A/xx

Links

-1 4-hydroxy-3-methoxycyclohexyl Chemical group 0.000 claims description 65
238000002360 preparation method Methods 0.000 claims description 59
150000001875 compounds Chemical class 0.000 claims description 44
HXEACLLIILLPRG-UHFFFAOYSA-N Pipecolic acid Chemical class OC(=O)C1CCCCN1 HXEACLLIILLPRG-UHFFFAOYSA-N 0.000 claims description 37
125000000217 alkyl group Chemical group 0.000 claims description 33
125000004432 carbon atoms Chemical group C* 0.000 claims description 31
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 31
239000002502 liposome Substances 0.000 claims description 25
125000004435 hydrogen atoms Chemical group [H]* 0.000 claims description 23
239000011780 sodium chloride Substances 0.000 claims description 18
HVYWMOMLDIMFJA-DPAQBDIFSA-N (3β)-Cholest-5-en-3-ol 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 claims description 17
GUBGYTABKSRVRQ-YOLKTULGSA-N Maltose Natural products O([C@@H]1[C@H](O)[C@@H](O)[C@H](O)O[C@H]1CO)[C@@H]1[C@H](O)[C@@H](O)[C@@H](O)[C@@H](CO)O1 GUBGYTABKSRVRQ-YOLKTULGSA-N 0.000 claims description 16
239000000787 lecithin Substances 0.000 claims description 15
235000010445 lecithin Nutrition 0.000 claims description 15
150000003839 salts Chemical class 0.000 claims description 15
125000003545 alkoxy group Chemical group 0.000 claims description 14
JLPULHDHAOZNQI-ZTIMHPMXSA-N 1-hexadecanoyl-2-(9Z,12Z-octadecadienoyl)-sn-glycero-3-phosphocholine Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCCCCCC\C=C/C\C=C/CCCCC JLPULHDHAOZNQI-ZTIMHPMXSA-N 0.000 claims description 13
229940067606 Lecithin Drugs 0.000 claims description 13
125000004043 oxo group Chemical group O=* 0.000 claims description 13
239000003120 macrolide antibiotic agent Substances 0.000 claims description 12
229910052799 carbon Inorganic materials 0.000 claims description 10
235000012000 cholesterol Nutrition 0.000 claims description 10
239000007924 injection Substances 0.000 claims description 10
150000002632 lipids Chemical class 0.000 claims description 10
125000003118 aryl group Chemical group 0.000 claims description 8
238000002347 injection Methods 0.000 claims description 8
229940107161 Cholesterol Drugs 0.000 claims description 7
150000001720 carbohydrates Chemical class 0.000 claims description 7
239000007787 solid Substances 0.000 claims description 7
125000003342 alkenyl group Chemical group 0.000 claims description 6
125000000623 heterocyclic group Chemical group 0.000 claims description 6
125000004430 oxygen atoms Chemical group O* 0.000 claims description 5
GUBGYTABKSRVRQ-UUNJERMWSA-N Lactose Natural products O([C@@H]1[C@H](O)[C@H](O)[C@H](O)O[C@@H]1CO)[C@H]1[C@@H](O)[C@@H](O)[C@H](O)[C@H](CO)O1 GUBGYTABKSRVRQ-UUNJERMWSA-N 0.000 claims description 4
230000015572 biosynthetic process Effects 0.000 claims description 4
239000012153 distilled water Substances 0.000 claims description 4
238000005755 formation reaction Methods 0.000 claims description 4
239000008101 lactose Substances 0.000 claims description 4
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 4
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 3
125000005842 heteroatoms Chemical group 0.000 claims description 3
XEEYBQQBJWHFJM-UHFFFAOYSA-N iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 3
125000004433 nitrogen atoms Chemical group N* 0.000 claims description 3
125000004434 sulfur atoms Chemical group 0.000 claims description 3
CFZGEMKIQUVTCC-UHFFFAOYSA-N octacos-18-ene-2,3,10,16-tetrone Chemical compound CCCCCCCCCC=CCC(=O)CCCCCC(=O)CCCCCCC(=O)C(C)=O CFZGEMKIQUVTCC-UHFFFAOYSA-N 0.000 claims description 2
125000002088 tosyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C([H])([H])[H])S(*)(=O)=O 0.000 claims description 2
KLGZELKXQMTEMM-UHFFFAOYSA-N hydride Chemical compound [H-] KLGZELKXQMTEMM-UHFFFAOYSA-N 0.000 claims 1
GUBGYTABKSRVRQ-QKKXKWKRSA-N lactose group Chemical group OC1[C@H](O)[C@@H](O)[C@H](O[C@H]2[C@H](O)[C@@H](O)[C@@H](O)[C@H](O2)CO)[C@H](O1)CO GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 claims 1
201000010099 disease Diseases 0.000 description 24
QJJXYPPXXYFBGM-LFZNUXCKSA-N Tacrolimus Chemical compound C1C[C@@H](O)[C@H](OC)C[C@@H]1\C=C(/C)[C@@H]1[C@H](C)[C@@H](O)CC(=O)[C@H](CC=C)/C=C(C)/C[C@H](C)C[C@H](OC)[C@H]([C@H](C[C@H]2C)OC)O[C@@]2(O)C(=O)C(=O)N2CCCC[C@H]2C(=O)O1 QJJXYPPXXYFBGM-LFZNUXCKSA-N 0.000 description 18
229960001967 Tacrolimus Drugs 0.000 description 17
125000002252 acyl group Chemical group 0.000 description 15
230000000694 effects Effects 0.000 description 12
239000006185 dispersion Substances 0.000 description 11
LFQSCWFLJHTTHZ-UHFFFAOYSA-N ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 11
210000004556 Brain Anatomy 0.000 description 10
239000003814 drug Substances 0.000 description 10
229940079593 drugs Drugs 0.000 description 10
125000001424 substituent group Chemical group 0.000 description 10
210000004369 Blood Anatomy 0.000 description 9
239000008280 blood Substances 0.000 description 9
208000006673 Asthma Diseases 0.000 description 8
210000002969 Egg Yolk Anatomy 0.000 description 8
235000013345 egg yolk Nutrition 0.000 description 8
230000000302 ischemic Effects 0.000 description 8
206010008118 Cerebral infarction Diseases 0.000 description 7
239000004480 active ingredient Substances 0.000 description 7
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 7
238000005516 engineering process Methods 0.000 description 7
RZVAJINKPMORJF-UHFFFAOYSA-N p-acetaminophenol Chemical compound CC(=O)NC1=CC=C(O)C=C1 RZVAJINKPMORJF-UHFFFAOYSA-N 0.000 description 7
150000003904 phospholipids Chemical class 0.000 description 7
239000000243 solution Substances 0.000 description 7
239000003381 stabilizer Substances 0.000 description 7
239000008215 water for injection Substances 0.000 description 7
125000001931 aliphatic group Chemical group 0.000 description 6
229940067631 Phospholipids Drugs 0.000 description 5
QFJCIRLUMZQUOT-HPLJOQBZSA-N Sirolimus Chemical compound C1C[C@@H](O)[C@H](OC)C[C@@H]1C[C@@H](C)[C@H]1OC(=O)[C@@H]2CCCCN2C(=O)C(=O)[C@](O)(O2)[C@H](C)CC[C@H]2C[C@H](OC)/C(C)=C/C=C/C=C/[C@@H](C)C[C@@H](C)C(=O)[C@H](OC)[C@H](O)/C(C)=C/[C@@H](C)C(=O)C1 QFJCIRLUMZQUOT-HPLJOQBZSA-N 0.000 description 5
238000006243 chemical reaction Methods 0.000 description 5
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 5
239000000203 mixture Substances 0.000 description 5
210000000056 organs Anatomy 0.000 description 5
239000002245 particle Substances 0.000 description 5
230000002265 prevention Effects 0.000 description 5
229960002930 sirolimus Drugs 0.000 description 5
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 description 5
206010003816 Autoimmune disease Diseases 0.000 description 4
206010023332 Keratitis Diseases 0.000 description 4
210000004185 Liver Anatomy 0.000 description 4
239000002253 acid Substances 0.000 description 4
201000004624 dermatitis Diseases 0.000 description 4
201000009910 diseases by infectious agent Diseases 0.000 description 4
230000001264 neutralization Effects 0.000 description 4
239000000047 product Substances 0.000 description 4
239000000126 substance Substances 0.000 description 4
239000010409 thin film Substances 0.000 description 4
125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 3
ZDQSOHOQTUFQEM-NURRSENYSA-N ASCOMYCIN Chemical compound C/C([C@H]1OC(=O)[C@@H]2CCCCN2C(=O)C(=O)[C@]2(O)O[C@@H]([C@H](C[C@H]2C)OC)[C@@H](OC)C[C@@H](C)C/C(C)=C/[C@H](C(C[C@H](O)[C@H]1C)=O)CC)=C\[C@@H]1CC[C@@H](O)[C@H](OC)C1 ZDQSOHOQTUFQEM-NURRSENYSA-N 0.000 description 3
229960001375 Lactose Drugs 0.000 description 3
241000700159 Rattus Species 0.000 description 3
ZDQSOHOQTUFQEM-XZQJPUKSSA-N ascomycin Chemical compound C/C([C@H]1OC(=O)[C@@H]2CCCCN2C(=O)C(=O)[C@]2(O)O[C@@H]([C@H](C[C@H]2C)OC)[C@@H](OC)C[C@@H](C)CC(C)=C[C@H](C(C[C@H](O)[C@H]1C)=O)CC)=C\[C@@H]1CC[C@@H](O)[C@H](OC)C1 ZDQSOHOQTUFQEM-XZQJPUKSSA-N 0.000 description 3
125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 3
125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 3
230000002490 cerebral Effects 0.000 description 3
150000001841 cholesterols Chemical class 0.000 description 3
230000001684 chronic Effects 0.000 description 3
231100000406 dermatitis Toxicity 0.000 description 3
RNPXCFINMKSQPQ-UHFFFAOYSA-N dicetyl hydrogen phosphate Chemical compound CCCCCCCCCCCCCCCCOP(O)(=O)OCCCCCCCCCCCCCCCC RNPXCFINMKSQPQ-UHFFFAOYSA-N 0.000 description 3
229940093541 dicetylphosphate Drugs 0.000 description 3
PEDCQBHIVMGVHV-UHFFFAOYSA-N glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
125000005553 heteroaryloxy group Chemical group 0.000 description 3
230000001506 immunosuppresive Effects 0.000 description 3
230000000968 intestinal Effects 0.000 description 3
GUBGYTABKSRVRQ-XLOQQCSPSA-N lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 description 3
230000001404 mediated Effects 0.000 description 3
230000000144 pharmacologic effect Effects 0.000 description 3
150000008103 phosphatidic acids Chemical class 0.000 description 3
229920000515 polycarbonate Polymers 0.000 description 3
239000004417 polycarbonate Substances 0.000 description 3
JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 3
210000001519 tissues Anatomy 0.000 description 3
230000000699 topical Effects 0.000 description 3
238000002054 transplantation Methods 0.000 description 3
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
ZAKBPRIDLSBYQQ-VHSXEESVSA-N 1,2-diacyl-sn-glycero-3-phospho-(1'-sn-glycerol) Chemical compound CC(=O)OC[C@@H](OC(C)=O)COP(O)(=O)OC[C@@H](O)CO ZAKBPRIDLSBYQQ-VHSXEESVSA-N 0.000 description 2
125000002373 5 membered heterocyclic group Chemical group 0.000 description 2
125000004070 6 membered heterocyclic group Chemical group 0.000 description 2
206010002026 Amyotrophic lateral sclerosis Diseases 0.000 description 2
206010003210 Arteriosclerosis Diseases 0.000 description 2
206010003246 Arthritis Diseases 0.000 description 2
210000000988 Bone and Bones Anatomy 0.000 description 2
208000000594 Bullous Pemphigoid Diseases 0.000 description 2
206010010744 Conjunctivitis allergic Diseases 0.000 description 2
206010060742 Endocrine ophthalmopathy Diseases 0.000 description 2
108090000790 Enzymes Proteins 0.000 description 2
102000004190 Enzymes Human genes 0.000 description 2
108060002921 FKBP2 Proteins 0.000 description 2
108060002918 FKBP6 Proteins 0.000 description 2
102100000319 FKBP9 Human genes 0.000 description 2
108060002920 FPR1 Proteins 0.000 description 2
210000001035 Gastrointestinal Tract Anatomy 0.000 description 2
206010018651 Graft versus host disease Diseases 0.000 description 2
210000002216 Heart Anatomy 0.000 description 2
206010003820 Hepatic autoimmune disease Diseases 0.000 description 2
206010019663 Hepatic failure Diseases 0.000 description 2
208000006454 Hepatitis Diseases 0.000 description 2
210000003734 Kidney Anatomy 0.000 description 2
208000001083 Kidney Disease Diseases 0.000 description 2
208000007903 Liver Failure Diseases 0.000 description 2
210000000865 Mononuclear Phagocyte System Anatomy 0.000 description 2
JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine Chemical class CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 2
LKQLRGMMMAHREN-YJFXYUILSA-N N-stearoylsphingosine-1-phosphocholine Chemical compound CCCCCCCCCCCCCCCCCC(=O)N[C@@H](COP([O-])(=O)OCC[N+](C)(C)C)[C@H](O)\C=C\CCCCCCCCCCCCC LKQLRGMMMAHREN-YJFXYUILSA-N 0.000 description 2
206010029240 Neuritis Diseases 0.000 description 2
JOXIMZWYDAKGHI-UHFFFAOYSA-N P-Toluenesulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
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UNJJBGNPUUVVFQ-ZJUUUORDSA-N Phosphatidylserine Chemical compound CCCC(=O)O[C@H](COC(=O)CC)COP(O)(=O)OC[C@H](N)C(O)=O UNJJBGNPUUVVFQ-ZJUUUORDSA-N 0.000 description 2
JUJWROOIHBZHMG-UHFFFAOYSA-O Pyridinium Chemical compound C1=CC=[NH+]C=C1 JUJWROOIHBZHMG-UHFFFAOYSA-O 0.000 description 2
210000003491 Skin Anatomy 0.000 description 2
208000006641 Skin Disease Diseases 0.000 description 2
108060002923 TIG Proteins 0.000 description 2
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125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 2
230000001154 acute Effects 0.000 description 2
239000000654 additive Substances 0.000 description 2
125000005115 alkyl carbamoyl group Chemical group 0.000 description 2
201000004384 alopecia Diseases 0.000 description 2
231100000360 alopecia Toxicity 0.000 description 2
230000001363 autoimmune Effects 0.000 description 2
125000000852 azido group Chemical group *N=[N+]=[N-] 0.000 description 2
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
WKBOTKDWSSQWDR-UHFFFAOYSA-N bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
239000000460 chlorine Substances 0.000 description 2
229910052801 chlorine Inorganic materials 0.000 description 2
ZAMOUSCENKQFHK-UHFFFAOYSA-N chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
238000002296 dynamic light scattering Methods 0.000 description 2
238000004945 emulsification Methods 0.000 description 2
125000003700 epoxy group Chemical group 0.000 description 2
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
238000000855 fermentation Methods 0.000 description 2
230000004151 fermentation Effects 0.000 description 2
238000007710 freezing Methods 0.000 description 2
229910052736 halogen Inorganic materials 0.000 description 2
150000002367 halogens Chemical class 0.000 description 2
231100000283 hepatitis Toxicity 0.000 description 2
NTYJJOPFIAHURM-UHFFFAOYSA-N histamine Chemical compound NCCC1=CN=CN1 NTYJJOPFIAHURM-UHFFFAOYSA-N 0.000 description 2
239000001257 hydrogen Substances 0.000 description 2
229910052739 hydrogen Inorganic materials 0.000 description 2
UFHFLCQGNIYNRP-UHFFFAOYSA-N hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
239000011630 iodine Substances 0.000 description 2
PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 2
229910052740 iodine Inorganic materials 0.000 description 2
201000010666 keratoconjunctivitis Diseases 0.000 description 2
201000009673 liver disease Diseases 0.000 description 2
231100000835 liver failure Toxicity 0.000 description 2
125000004092 methylthiomethyl group Chemical group [H]C([H])([H])SC([H])([H])* 0.000 description 2
201000005962 mycosis fungoide Diseases 0.000 description 2
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 2
125000001181 organosilyl group Chemical group [SiH3]* 0.000 description 2
229910052760 oxygen Inorganic materials 0.000 description 2
239000001301 oxygen Substances 0.000 description 2
MYMOFIZGZYHOMD-UHFFFAOYSA-N oxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 description 2
125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 description 2
125000001095 phosphatidyl group Chemical group 0.000 description 2
150000008104 phosphatidylethanolamines Chemical class 0.000 description 2
150000003905 phosphatidylinositols Chemical class 0.000 description 2
125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 2
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
210000002345 respiratory system Anatomy 0.000 description 2
108060007134 rot Proteins 0.000 description 2
201000000306 sarcoidosis Diseases 0.000 description 2
230000035939 shock Effects 0.000 description 2
125000003808 silyl group Chemical class [H][Si]([H])([H])[*] 0.000 description 2
239000012453 solvate Substances 0.000 description 2
239000002904 solvent Substances 0.000 description 2
125000001981 tert-butyldimethylsilyl group Chemical group [H]C([H])([H])[Si]([H])(C([H])([H])[H])[*]C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
125000000037 tert-butyldiphenylsilyl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1[Si]([H])([*]C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 2
XVTUQDWPJJBEHJ-KZCWQMDCSA-N tetrastearoyl cardiolipin Chemical compound CCCCCCCCCCCCCCCCCC(=O)OC[C@@H](OC(=O)CCCCCCCCCCCCCCCCC)CO[P@@](O)(=O)OCC(O)CO[P@](O)(=O)OC[C@H](OC(=O)CCCCCCCCCCCCCCCCC)COC(=O)CCCCCCCCCCCCCCCCC XVTUQDWPJJBEHJ-KZCWQMDCSA-N 0.000 description 2
201000010875 transient cerebral ischemia Diseases 0.000 description 2
WQZGKKKJIJFFOK-VFUOTHLCSA-N β-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
WSVLPVUVIUVCRA-RJMJUYIDSA-N (2R,3R,4S,5R,6S)-2-(hydroxymethyl)-6-[(2R,3S,4R,5R)-4,5,6-trihydroxy-2-(hydroxymethyl)oxan-3-yl]oxyoxane-3,4,5-triol;hydrate Chemical compound O.O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)OC(O)[C@H](O)[C@H]1O WSVLPVUVIUVCRA-RJMJUYIDSA-N 0.000 description 1
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VYKNVAHOUNIVTQ-UHFFFAOYSA-N 1,2,2,3,3-pentamethylpiperidine Chemical class CN1CCCC(C)(C)C1(C)C VYKNVAHOUNIVTQ-UHFFFAOYSA-N 0.000 description 1
NRJAVPSFFCBXDT-HUESYALOSA-N 1,2-distearoyl-sn-glycero-3-phosphocholine Chemical compound CCCCCCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCCCCCCCCCCCCCCCC NRJAVPSFFCBXDT-HUESYALOSA-N 0.000 description 1
YAMUFBLWGFFICM-PTGWMXDISA-N 1-O-oleoyl-sn-glycero-3-phosphocholine Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OC[C@@H](O)COP([O-])(=O)OCC[N+](C)(C)C YAMUFBLWGFFICM-PTGWMXDISA-N 0.000 description 1
SLKDGVPOSSLUAI-UHFFFAOYSA-N 2-azaniumylethyl 2,3-di(hexadecanoyloxy)propyl phosphate Chemical compound CCCCCCCCCCCCCCCC(=O)OCC(COP(O)(=O)OCCN)OC(=O)CCCCCCCCCCCCCCC SLKDGVPOSSLUAI-UHFFFAOYSA-N 0.000 description 1
ISULLEUFOQSBGY-UHFFFAOYSA-N 4-Phenyl-1,2,4-triazole-3,5-dione Chemical compound O=C1N=NC(=O)N1C1=CC=CC=C1 ISULLEUFOQSBGY-UHFFFAOYSA-N 0.000 description 1
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208000007788 Acute Liver Failure Diseases 0.000 description 1
206010000804 Acute hepatic failure Diseases 0.000 description 1
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206010001897 Alzheimer's disease Diseases 0.000 description 1
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206010002091 Anaesthesia Diseases 0.000 description 1
208000009094 Anemia, Hemolytic, Autoimmune Diseases 0.000 description 1
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210000000702 Aorta, Abdominal Anatomy 0.000 description 1
206010002967 Aplastic anaemia Diseases 0.000 description 1
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MXPA/A/2001/008326A 2001-08-16 MXPA01008326A (zh)