PT100997B - Processo para preparacao de composicoes farmaceuticas uteis para a reducao ou o tratamento de pereturbacoes da microcirculacao provocadas pela administracao de meios de contraste para raios x, nmr ou ultrassons por incorporacao de derivados de prostaciclinas - Google Patents
Processo para preparacao de composicoes farmaceuticas uteis para a reducao ou o tratamento de pereturbacoes da microcirculacao provocadas pela administracao de meios de contraste para raios x, nmr ou ultrassons por incorporacao de derivados de prostaciclinas Download PDFInfo
- Publication number
- PT100997B PT100997B PT100997A PT10099792A PT100997B PT 100997 B PT100997 B PT 100997B PT 100997 A PT100997 A PT 100997A PT 10099792 A PT10099792 A PT 10099792A PT 100997 B PT100997 B PT 100997B
- Authority
- PT
- Portugal
- Prior art keywords
- group
- administration
- clathrate
- contrast media
- reduction
- Prior art date
Links
- 239000002872 contrast media Substances 0.000 title claims abstract description 48
- 229940039231 contrast media Drugs 0.000 title claims abstract description 21
- 238000004519 manufacturing process Methods 0.000 title claims abstract 3
- 230000009467 reduction Effects 0.000 title claims description 16
- 230000004089 microcirculation Effects 0.000 title claims description 15
- 238000011282 treatment Methods 0.000 title claims description 13
- 239000008194 pharmaceutical composition Substances 0.000 title claims description 6
- KAQKFAOMNZTLHT-VVUHWYTRSA-N epoprostenol Chemical class O1C(=CCCCC(O)=O)C[C@@H]2[C@@H](/C=C/[C@@H](O)CCCCC)[C@H](O)C[C@@H]21 KAQKFAOMNZTLHT-VVUHWYTRSA-N 0.000 title claims description 3
- 238000010348 incorporation Methods 0.000 title 1
- 150000003815 prostacyclins Chemical class 0.000 claims abstract description 20
- 238000000034 method Methods 0.000 claims description 14
- 230000008569 process Effects 0.000 claims description 14
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 12
- 238000002604 ultrasonography Methods 0.000 claims description 12
- 239000001257 hydrogen Substances 0.000 claims description 10
- 229910052739 hydrogen Inorganic materials 0.000 claims description 10
- 125000000217 alkyl group Chemical group 0.000 claims description 8
- 238000002360 preparation method Methods 0.000 claims description 8
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 7
- 150000003839 salts Chemical class 0.000 claims description 5
- 229920000858 Cyclodextrin Polymers 0.000 claims description 4
- ARUGKOZUKWAXDS-SEWALLKFSA-N cicaprost Chemical compound C1\C(=C/COCC(O)=O)C[C@@H]2[C@@H](C#C[C@@H](O)[C@@H](C)CC#CCC)[C@H](O)C[C@@H]21 ARUGKOZUKWAXDS-SEWALLKFSA-N 0.000 claims description 4
- 229950000634 cicaprost Drugs 0.000 claims description 4
- 239000002502 liposome Substances 0.000 claims description 4
- 229920006395 saturated elastomer Polymers 0.000 claims description 4
- ZLJOKYGJNOQXDP-OZUBPDBUSA-N 3-[(z)-[(3ar,4r,5r,6as)-4-[(e,3s)-3-cyclohexyl-3-hydroxyprop-1-enyl]-5-hydroxy-3,3a,4,5,6,6a-hexahydrocyclopenta[b]furan-2-ylidene]methyl]benzoic acid Chemical group O([C@H]1C[C@@H](O)[C@@H]([C@H]1C1)/C=C/[C@@H](O)C2CCCCC2)\C1=C/C1=CC=CC(C(O)=O)=C1 ZLJOKYGJNOQXDP-OZUBPDBUSA-N 0.000 claims description 3
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 3
- 229910052731 fluorine Inorganic materials 0.000 claims description 3
- 239000011737 fluorine Substances 0.000 claims description 3
- SRVNVLSGXFMMLE-UVZUILRGSA-M sodium;(5e)-5-[(3as,4r,5r,6as)-5-hydroxy-4-[(1e,3s)-3-hydroxy-5,9-dimethyldeca-1,8-dienyl]-3,3a,4,5,6,6a-hexahydro-1h-pentalen-2-ylidene]pentanoate Chemical compound [Na+].C1\C(=C/CCCC([O-])=O)C[C@@H]2[C@@H](/C=C/[C@@H](O)CC(CCC=C(C)C)C)[C@H](O)C[C@@H]21 SRVNVLSGXFMMLE-UVZUILRGSA-M 0.000 claims description 3
- 125000004429 atom Chemical group 0.000 claims description 2
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 2
- 230000004048 modification Effects 0.000 claims 3
- 238000012986 modification Methods 0.000 claims 3
- DKLGLHQHLFISGJ-YLBFUXKPSA-N (5e)-5-[(3as,4r,5r,6as)-4-[(e,3s)-3-cyclopentyl-3-hydroxyprop-1-enyl]-5-hydroxy-3,3a,4,5,6,6a-hexahydro-1h-pentalen-2-ylidene]pentanoic acid Chemical compound C1([C@@H](\C=C\[C@@H]2[C@H]3CC(/C[C@H]3C[C@H]2O)=C/CCCC(O)=O)O)CCCC1 DKLGLHQHLFISGJ-YLBFUXKPSA-N 0.000 claims 2
- COTOHBYFKOEMEU-PDWIHATRSA-N (5e)-5-[(3as,4s,5r,6as)-5-hydroxy-4-[(3s)-3-hydroxynon-1-ynyl]-3,3a,4,5,6,6a-hexahydro-1h-pentalen-2-ylidene]pentanoic acid Chemical compound C1\C(=C/CCCC(O)=O)C[C@@H]2[C@@H](C#C[C@@H](O)CCCCCC)[C@H](O)C[C@@H]21 COTOHBYFKOEMEU-PDWIHATRSA-N 0.000 claims 2
- MAUUNYHAXGTMMQ-AMXXQSRZSA-N 4-[(2e)-2-[(3as,4s,5r,6as)-5-hydroxy-4-[(3s,4s)-3-hydroxy-4-methylnona-1,6-diynyl]-3,3a,4,5,6,6a-hexahydro-1h-pentalen-2-ylidene]ethoxy]butanoic acid Chemical compound C1\C(=C/COCCCC(O)=O)C[C@@H]2[C@@H](C#C[C@@H](O)[C@@H](C)CC#CCC)[C@H](O)C[C@@H]21 MAUUNYHAXGTMMQ-AMXXQSRZSA-N 0.000 claims 2
- VKPYUUBEDXIQIB-QBPWRKFFSA-N Ciprostene Chemical group C1\C(=C/CCCC(O)=O)C[C@@H]2[C@@H](/C=C/[C@@H](O)CCCCC)[C@H](O)C[C@@]21C VKPYUUBEDXIQIB-QBPWRKFFSA-N 0.000 claims 2
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 claims 2
- 239000004480 active ingredient Substances 0.000 claims 2
- 229950001358 ataprost Drugs 0.000 claims 2
- 229960002890 beraprost Drugs 0.000 claims 2
- CTPOHARTNNSRSR-APJZLKAGSA-N beraprost Chemical compound O([C@H]1C[C@@H](O)[C@@H]([C@@H]21)/C=C/[C@@H](O)C(C)CC#CC)C1=C2C=CC=C1CCCC(O)=O CTPOHARTNNSRSR-APJZLKAGSA-N 0.000 claims 2
- 229950006293 eptaloprost Drugs 0.000 claims 2
- 150000002431 hydrogen Chemical class 0.000 claims 2
- 229960001123 epoprostenol Drugs 0.000 claims 1
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims 1
- IQKAWAUTOKVMLE-ZSESPEEFSA-M treprostinil sodium Chemical compound [Na+].C1=CC=C(OCC([O-])=O)C2=C1C[C@@H]1[C@@H](CC[C@@H](O)CCCCC)[C@H](O)C[C@@H]1C2 IQKAWAUTOKVMLE-ZSESPEEFSA-M 0.000 claims 1
- 239000008177 pharmaceutical agent Substances 0.000 abstract 1
- 229960002240 iloprost Drugs 0.000 description 23
- HIFJCPQKFCZDDL-ACWOEMLNSA-N iloprost Chemical compound C1\C(=C/CCCC(O)=O)C[C@@H]2[C@@H](/C=C/[C@@H](O)C(C)CC#CC)[C@H](O)C[C@@H]21 HIFJCPQKFCZDDL-ACWOEMLNSA-N 0.000 description 23
- 238000002347 injection Methods 0.000 description 23
- 239000007924 injection Substances 0.000 description 23
- 210000000601 blood cell Anatomy 0.000 description 19
- 241001465754 Metazoa Species 0.000 description 18
- 239000000243 solution Substances 0.000 description 17
- 230000037396 body weight Effects 0.000 description 15
- 210000003743 erythrocyte Anatomy 0.000 description 15
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 13
- 238000011835 investigation Methods 0.000 description 12
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 11
- 208000035475 disorder Diseases 0.000 description 10
- 230000010412 perfusion Effects 0.000 description 10
- 230000000699 topical effect Effects 0.000 description 9
- YVPYQUNUQOZFHG-UHFFFAOYSA-N amidotrizoic acid Chemical compound CC(=O)NC1=C(I)C(NC(C)=O)=C(I)C(C(O)=O)=C1I YVPYQUNUQOZFHG-UHFFFAOYSA-N 0.000 description 8
- 210000004027 cell Anatomy 0.000 description 8
- 210000000936 intestine Anatomy 0.000 description 8
- 238000001990 intravenous administration Methods 0.000 description 8
- 238000005259 measurement Methods 0.000 description 7
- 239000011780 sodium chloride Substances 0.000 description 7
- 238000001228 spectrum Methods 0.000 description 7
- 229960005423 diatrizoate Drugs 0.000 description 6
- 238000001361 intraarterial administration Methods 0.000 description 6
- 210000000813 small intestine Anatomy 0.000 description 6
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 5
- 150000001875 compounds Chemical class 0.000 description 5
- 230000000694 effects Effects 0.000 description 5
- -1 hydroxymethylene group Chemical class 0.000 description 5
- 210000000713 mesentery Anatomy 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- 210000004877 mucosa Anatomy 0.000 description 5
- 238000011160 research Methods 0.000 description 5
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 4
- 241000700159 Rattus Species 0.000 description 4
- 208000007536 Thrombosis Diseases 0.000 description 4
- 230000009471 action Effects 0.000 description 4
- 230000036760 body temperature Effects 0.000 description 4
- 230000007423 decrease Effects 0.000 description 4
- 230000005764 inhibitory process Effects 0.000 description 4
- 210000003462 vein Anatomy 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 239000003708 ampul Substances 0.000 description 3
- 210000000709 aorta Anatomy 0.000 description 3
- 239000006185 dispersion Substances 0.000 description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- 244000144993 groups of animals Species 0.000 description 3
- 238000012771 intravital microscopy Methods 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- 239000002245 particle Substances 0.000 description 3
- 210000001519 tissue Anatomy 0.000 description 3
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 230000001464 adherent effect Effects 0.000 description 2
- 239000002671 adjuvant Substances 0.000 description 2
- 230000002776 aggregation Effects 0.000 description 2
- 238000004220 aggregation Methods 0.000 description 2
- 230000004872 arterial blood pressure Effects 0.000 description 2
- 210000001772 blood platelet Anatomy 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 210000001168 carotid artery common Anatomy 0.000 description 2
- 230000004087 circulation Effects 0.000 description 2
- 238000013480 data collection Methods 0.000 description 2
- 210000003038 endothelium Anatomy 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 210000003191 femoral vein Anatomy 0.000 description 2
- 229930182830 galactose Natural products 0.000 description 2
- 210000000609 ganglia Anatomy 0.000 description 2
- 238000001727 in vivo Methods 0.000 description 2
- 239000000644 isotonic solution Substances 0.000 description 2
- 210000003734 kidney Anatomy 0.000 description 2
- 210000000265 leukocyte Anatomy 0.000 description 2
- 238000012423 maintenance Methods 0.000 description 2
- 239000004005 microsphere Substances 0.000 description 2
- 210000004088 microvessel Anatomy 0.000 description 2
- 230000003533 narcotic effect Effects 0.000 description 2
- 210000000056 organ Anatomy 0.000 description 2
- 229940021222 peritoneal dialysis isotonic solution Drugs 0.000 description 2
- 230000000144 pharmacologic effect Effects 0.000 description 2
- 238000011321 prophylaxis Methods 0.000 description 2
- 210000002784 stomach Anatomy 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 238000002560 therapeutic procedure Methods 0.000 description 2
- KZYHGCLDUQBASN-UHFFFAOYSA-N 1-n,1-n,3-n,3-n,5-n,5-n-hexakis(2-hydroxyethyl)-2,4,6-triiodobenzene-1,3,5-tricarboxamide Chemical compound OCCN(CCO)C(=O)C1=C(I)C(C(=O)N(CCO)CCO)=C(I)C(C(=O)N(CCO)CCO)=C1I KZYHGCLDUQBASN-UHFFFAOYSA-N 0.000 description 1
- HXYJZJOQRLOUPP-UHFFFAOYSA-N 2-(hydroxymethyl)propane-1,2,3-triol Chemical compound OCC(O)(CO)CO HXYJZJOQRLOUPP-UHFFFAOYSA-N 0.000 description 1
- 125000004813 2-ethylethylene group Chemical group [H]C([H])([H])C([H])([H])C([H])([*:2])C([H])([H])[*:1] 0.000 description 1
- 102000009027 Albumins Human genes 0.000 description 1
- 108010088751 Albumins Proteins 0.000 description 1
- 206010003210 Arteriosclerosis Diseases 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- 206010011091 Coronary artery thrombosis Diseases 0.000 description 1
- 229920001651 Cyanoacrylate Polymers 0.000 description 1
- 229920001353 Dextrin Polymers 0.000 description 1
- 239000004375 Dextrin Substances 0.000 description 1
- 241000282324 Felis Species 0.000 description 1
- 229910052688 Gadolinium Inorganic materials 0.000 description 1
- HTTJABKRGRZYRN-UHFFFAOYSA-N Heparin Chemical compound OC1C(NC(=O)C)C(O)OC(COS(O)(=O)=O)C1OC1C(OS(O)(=O)=O)C(O)C(OC2C(C(OS(O)(=O)=O)C(OC3C(C(O)C(O)C(O3)C(O)=O)OS(O)(=O)=O)C(CO)O2)NS(O)(=O)=O)C(C(O)=O)O1 HTTJABKRGRZYRN-UHFFFAOYSA-N 0.000 description 1
- PWHULOQIROXLJO-UHFFFAOYSA-N Manganese Chemical compound [Mn] PWHULOQIROXLJO-UHFFFAOYSA-N 0.000 description 1
- MWCLLHOVUTZFKS-UHFFFAOYSA-N Methyl cyanoacrylate Chemical compound COC(=O)C(=C)C#N MWCLLHOVUTZFKS-UHFFFAOYSA-N 0.000 description 1
- BAQCROVBDNBEEB-UBYUBLNFSA-N Metrizamide Chemical compound CC(=O)N(C)C1=C(I)C(NC(C)=O)=C(I)C(C(=O)N[C@@H]2[C@H]([C@H](O)[C@@H](CO)OC2O)O)=C1I BAQCROVBDNBEEB-UBYUBLNFSA-N 0.000 description 1
- QPCDCPDFJACHGM-UHFFFAOYSA-N N,N-bis{2-[bis(carboxymethyl)amino]ethyl}glycine Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(=O)O)CCN(CC(O)=O)CC(O)=O QPCDCPDFJACHGM-UHFFFAOYSA-N 0.000 description 1
- 208000002193 Pain Diseases 0.000 description 1
- 208000010513 Stupor Diseases 0.000 description 1
- WDLRUFUQRNWCPK-UHFFFAOYSA-N Tetraxetan Chemical compound OC(=O)CN1CCN(CC(O)=O)CCN(CC(O)=O)CCN(CC(O)=O)CC1 WDLRUFUQRNWCPK-UHFFFAOYSA-N 0.000 description 1
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 1
- LPQOADBMXVRBNX-UHFFFAOYSA-N ac1ldcw0 Chemical compound Cl.C1CN(C)CCN1C1=C(F)C=C2C(=O)C(C(O)=O)=CN3CCSC1=C32 LPQOADBMXVRBNX-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Substances CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 1
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
- 230000009858 acid secretion Effects 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 229910001854 alkali hydroxide Inorganic materials 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 125000002947 alkylene group Chemical group 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 238000010171 animal model Methods 0.000 description 1
- 239000005557 antagonist Substances 0.000 description 1
- 230000003266 anti-allergic effect Effects 0.000 description 1
- 210000002565 arteriole Anatomy 0.000 description 1
- 208000011775 arteriosclerosis disease Diseases 0.000 description 1
- 210000001367 artery Anatomy 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 210000004369 blood Anatomy 0.000 description 1
- 239000008280 blood Substances 0.000 description 1
- 230000008499 blood brain barrier function Effects 0.000 description 1
- 230000017531 blood circulation Effects 0.000 description 1
- 230000023555 blood coagulation Effects 0.000 description 1
- 230000036772 blood pressure Effects 0.000 description 1
- 210000004204 blood vessel Anatomy 0.000 description 1
- 210000001218 blood-brain barrier Anatomy 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000004063 butyryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 230000002425 cardiocirculatory effect Effects 0.000 description 1
- 230000002490 cerebral effect Effects 0.000 description 1
- 238000012512 characterization method Methods 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 230000035606 childbirth Effects 0.000 description 1
- 229950009941 chloralose Drugs 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 208000029078 coronary artery disease Diseases 0.000 description 1
- 208000002528 coronary thrombosis Diseases 0.000 description 1
- 210000004351 coronary vessel Anatomy 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 235000019425 dextrin Nutrition 0.000 description 1
- 238000003745 diagnosis Methods 0.000 description 1
- 238000000502 dialysis Methods 0.000 description 1
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 1
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 239000002934 diuretic Substances 0.000 description 1
- 229940030606 diuretics Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 210000002889 endothelial cell Anatomy 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 238000006266 etherification reaction Methods 0.000 description 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
- 230000003480 fibrinolytic effect Effects 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- 230000004927 fusion Effects 0.000 description 1
- HZHFFEYYPYZMNU-UHFFFAOYSA-K gadodiamide Chemical compound [Gd+3].CNC(=O)CN(CC([O-])=O)CCN(CC([O-])=O)CCN(CC([O-])=O)CC(=O)NC HZHFFEYYPYZMNU-UHFFFAOYSA-K 0.000 description 1
- UIWYJDYFSGRHKR-UHFFFAOYSA-N gadolinium atom Chemical compound [Gd] UIWYJDYFSGRHKR-UHFFFAOYSA-N 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 238000002615 hemofiltration Methods 0.000 description 1
- 230000023597 hemostasis Effects 0.000 description 1
- 229960002897 heparin Drugs 0.000 description 1
- 229920000669 heparin Polymers 0.000 description 1
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- 150000004679 hydroxides Chemical class 0.000 description 1
- 230000001771 impaired effect Effects 0.000 description 1
- 201000006747 infectious mononucleosis Diseases 0.000 description 1
- 150000007529 inorganic bases Chemical class 0.000 description 1
- 230000000968 intestinal effect Effects 0.000 description 1
- 238000007912 intraperitoneal administration Methods 0.000 description 1
- 238000010253 intravenous injection Methods 0.000 description 1
- 229940029355 iodipamide Drugs 0.000 description 1
- NTHXOOBQLCIOLC-UHFFFAOYSA-N iohexol Chemical compound OCC(O)CN(C(=O)C)C1=C(I)C(C(=O)NCC(O)CO)=C(I)C(C(=O)NCC(O)CO)=C1I NTHXOOBQLCIOLC-UHFFFAOYSA-N 0.000 description 1
- 229960001025 iohexol Drugs 0.000 description 1
- DGAIEPBNLOQYER-UHFFFAOYSA-N iopromide Chemical compound COCC(=O)NC1=C(I)C(C(=O)NCC(O)CO)=C(I)C(C(=O)N(C)CC(O)CO)=C1I DGAIEPBNLOQYER-UHFFFAOYSA-N 0.000 description 1
- 229960002603 iopromide Drugs 0.000 description 1
- 229950011065 iosimide Drugs 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 230000000302 ischemic effect Effects 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 230000003902 lesion Effects 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 210000004185 liver Anatomy 0.000 description 1
- 229910052748 manganese Inorganic materials 0.000 description 1
- 239000011572 manganese Substances 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 1
- 229960000554 metrizamide Drugs 0.000 description 1
- 208000010125 myocardial infarction Diseases 0.000 description 1
- 210000004165 myocardium Anatomy 0.000 description 1
- LHMRRSXZHHQVCE-UHFFFAOYSA-N n-hydroxy-n-propylprop-2-enamide Chemical compound CCCN(O)C(=O)C=C LHMRRSXZHHQVCE-UHFFFAOYSA-N 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 210000002220 organoid Anatomy 0.000 description 1
- 230000001151 other effect Effects 0.000 description 1
- 230000036407 pain Effects 0.000 description 1
- 210000000496 pancreas Anatomy 0.000 description 1
- 230000001717 pathogenic effect Effects 0.000 description 1
- 230000001575 pathological effect Effects 0.000 description 1
- 229940014569 pentam Drugs 0.000 description 1
- YBVNFKZSMZGRAD-UHFFFAOYSA-N pentamidine isethionate Chemical compound OCCS(O)(=O)=O.OCCS(O)(=O)=O.C1=CC(C(=N)N)=CC=C1OCCCCCOC1=CC=C(C(N)=N)C=C1 YBVNFKZSMZGRAD-UHFFFAOYSA-N 0.000 description 1
- 208000030613 peripheral artery disease Diseases 0.000 description 1
- 230000002093 peripheral effect Effects 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 210000002381 plasma Anatomy 0.000 description 1
- 230000035935 pregnancy Effects 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 150000003180 prostaglandins Chemical class 0.000 description 1
- 230000002685 pulmonary effect Effects 0.000 description 1
- 230000036593 pulmonary vascular resistance Effects 0.000 description 1
- 230000010349 pulsation Effects 0.000 description 1
- 238000002633 shock therapy Methods 0.000 description 1
- 230000003595 spectral effect Effects 0.000 description 1
- 230000000638 stimulation Effects 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 230000009885 systemic effect Effects 0.000 description 1
- 229950002177 taprostene Drugs 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 125000001412 tetrahydropyranyl group Chemical group 0.000 description 1
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 1
- 230000009424 thromboembolic effect Effects 0.000 description 1
- 230000001732 thrombotic effect Effects 0.000 description 1
- RZWIIPASKMUIAC-VQTJNVASSA-N thromboxane Chemical compound CCCCCCCC[C@H]1OCCC[C@@H]1CCCCCCC RZWIIPASKMUIAC-VQTJNVASSA-N 0.000 description 1
- 238000002054 transplantation Methods 0.000 description 1
- 125000003258 trimethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])[*:1] 0.000 description 1
- 230000002792 vascular Effects 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B82—NANOTECHNOLOGY
- B82Y—SPECIFIC USES OR APPLICATIONS OF NANOSTRUCTURES; MEASUREMENT OR ANALYSIS OF NANOSTRUCTURES; MANUFACTURE OR TREATMENT OF NANOSTRUCTURES
- B82Y5/00—Nanobiotechnology or nanomedicine, e.g. protein engineering or drug delivery
-
- 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
- A61K31/557—Eicosanoids, e.g. leukotrienes or prostaglandins
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
- A61K47/50—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates
- A61K47/69—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the conjugate being characterised by physical or galenical forms, e.g. emulsion, particle, inclusion complex, stent or kit
- A61K47/6949—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the conjugate being characterised by physical or galenical forms, e.g. emulsion, particle, inclusion complex, stent or kit inclusion complexes, e.g. clathrates, cavitates or fullerenes
- A61K47/6951—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the conjugate being characterised by physical or galenical forms, e.g. emulsion, particle, inclusion complex, stent or kit inclusion complexes, e.g. clathrates, cavitates or fullerenes using cyclodextrin
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K49/00—Preparations for testing in vivo
- A61K49/0002—General or multifunctional contrast agents, e.g. chelated agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/10—Dispersions; Emulsions
- A61K9/127—Synthetic bilayered vehicles, e.g. liposomes or liposomes with cholesterol as the only non-phosphatidyl surfactant
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- Engineering & Computer Science (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Epidemiology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Nanotechnology (AREA)
- Medical Informatics (AREA)
- Biotechnology (AREA)
- General Engineering & Computer Science (AREA)
- Biophysics (AREA)
- Molecular Biology (AREA)
- Crystallography & Structural Chemistry (AREA)
- Dispersion Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Heart & Thoracic Surgery (AREA)
- Cardiology (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicinal Preparation (AREA)
- Medicines Containing Antibodies Or Antigens For Use As Internal Diagnostic Agents (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Furan Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE4135193A DE4135193C1 (https=) | 1991-10-22 | 1991-10-22 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| PT100997A PT100997A (pt) | 1994-01-31 |
| PT100997B true PT100997B (pt) | 1999-10-29 |
Family
ID=6443371
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PT100997A PT100997B (pt) | 1991-10-22 | 1992-10-22 | Processo para preparacao de composicoes farmaceuticas uteis para a reducao ou o tratamento de pereturbacoes da microcirculacao provocadas pela administracao de meios de contraste para raios x, nmr ou ultrassons por incorporacao de derivados de prostaciclinas |
Country Status (11)
| Country | Link |
|---|---|
| US (1) | US5814301A (https=) |
| EP (1) | EP0609336B1 (https=) |
| JP (1) | JPH07500585A (https=) |
| AT (1) | ATE162718T1 (https=) |
| CA (1) | CA2121838A1 (https=) |
| DE (2) | DE4135193C1 (https=) |
| DK (1) | DK0609336T3 (https=) |
| ES (1) | ES2114570T3 (https=) |
| GR (1) | GR3026324T3 (https=) |
| PT (1) | PT100997B (https=) |
| WO (1) | WO1993007875A1 (https=) |
Families Citing this family (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE4446694A1 (de) * | 1994-12-09 | 1996-06-13 | Schering Ag | Verwendung von Zusätzen zu Kontrastmitteln zur Verbesserung der Bildgebung |
| US6774278B1 (en) | 1995-06-07 | 2004-08-10 | Cook Incorporated | Coated implantable medical device |
| SK101398A3 (en) * | 1996-01-25 | 1998-12-02 | Schering Ag | Improved concentrated injection and infusion solutions for intravenous administration |
| KR100638684B1 (ko) * | 1997-11-14 | 2006-10-27 | 유나이티드 세러퓨틱스 코오포레이션 | 말초 혈관 질환의 치료를 위한 9-데옥시-2',9-알파-메타노-3-옥사-4,5,6-트리노르-3,7-(1',3'-인터페닐렌)-13,14-디하이드로-프로스타글란딘 에프1의 용도 |
| WO2000076496A1 (en) * | 1999-06-14 | 2000-12-21 | Toray Industries, Inc. | Tumor tissue accumulation enhancers for drugs |
| US20020147223A1 (en) * | 1999-06-14 | 2002-10-10 | Hiroshi Maeda | Agent for enhancing accumulation of drugs in tumor tissues |
| DE10115740A1 (de) * | 2001-03-26 | 2002-10-02 | Ulrich Speck | Zubereitung für die Restenoseprophylaxe |
| DE10244847A1 (de) | 2002-09-20 | 2004-04-01 | Ulrich Prof. Dr. Speck | Medizinische Vorrichtung zur Arzneimittelabgabe |
| ES2622471T5 (es) | 2003-05-22 | 2020-07-23 | United Therapeutics Corp | Compuestos y procedimientos para la administración de análogos de prostaciclina |
| WO2005099680A2 (en) * | 2004-04-12 | 2005-10-27 | United Therapeutics, Inc. | Use of treprostinil to treat neuropathic diabetic foot ulcers |
| JP2016517410A (ja) | 2013-03-14 | 2016-06-16 | ユナイテッド セラピューティクス コーポレイション | トレプロスチニルの固体形態 |
| AU2019339401B9 (en) * | 2018-09-14 | 2022-11-03 | Pharmosa Biopharm Inc. | Pharmaceutical composition for controlled release of weak acid drugs and uses thereof |
Family Cites Families (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2845770A1 (de) * | 1978-10-19 | 1980-04-30 | Schering Ag | Neue prostacyclin-derivate und verfahren zu ihrer herstellung |
| DE3204443A1 (de) * | 1982-02-08 | 1983-08-18 | Schering Ag, 1000 Berlin Und 4619 Bergkamen | Neue carbacycline, verfahren zu ihrer herstellung und ihre verwendung als arzneimittel |
| DE3448257C2 (en) * | 1984-07-25 | 1988-08-18 | Schering Ag, 1000 Berlin Und 4709 Bergkamen, De | Cytoprotective action of prostacyclin derivatives on the kidney |
| US4820732A (en) * | 1985-10-04 | 1989-04-11 | The Upjohn Company | Method and compositions for reducing dysfunction in angioplasty procedures |
| DE3608088C2 (de) * | 1986-03-07 | 1995-11-16 | Schering Ag | Pharmazeutische Präparate, enthaltend Cyclodextrinclathrate von Carbacyclinderivaten |
| US4955878A (en) * | 1986-04-04 | 1990-09-11 | Biotechnology, Inc. | Kit for preventing or treating arterial dysfunction resulting from angioplasty procedures |
| SE459806B (sv) * | 1987-11-23 | 1989-08-07 | Nils Enar Nilsson | Anordning foer foerflyttning av en foersta del relativt en andra del |
| DE3740838A1 (de) * | 1987-11-27 | 1989-06-08 | Schering Ag | Cyclodextrinclathrate von 5-cyano-prostacyclinderivaten und ihre verwendung als arzneimittel |
| CA2010511A1 (en) * | 1989-03-01 | 1990-09-01 | Roberto L. Ceriani | Method of enhancing cancer therapy by administration of unsaturated fatty acids |
| JPH0669966B2 (ja) * | 1989-07-05 | 1994-09-07 | 株式会社ミドリ十字 | 血管造影補助剤 |
-
1991
- 1991-10-22 DE DE4135193A patent/DE4135193C1/de not_active Expired - Fee Related
-
1992
- 1992-10-22 US US08/232,006 patent/US5814301A/en not_active Expired - Fee Related
- 1992-10-22 DE DE59209175T patent/DE59209175D1/de not_active Expired - Fee Related
- 1992-10-22 ES ES92922216T patent/ES2114570T3/es not_active Expired - Lifetime
- 1992-10-22 JP JP5507355A patent/JPH07500585A/ja active Pending
- 1992-10-22 AT AT92922216T patent/ATE162718T1/de not_active IP Right Cessation
- 1992-10-22 PT PT100997A patent/PT100997B/pt not_active IP Right Cessation
- 1992-10-22 EP EP92922216A patent/EP0609336B1/de not_active Expired - Lifetime
- 1992-10-22 CA CA002121838A patent/CA2121838A1/en not_active Abandoned
- 1992-10-22 DK DK92922216T patent/DK0609336T3/da active
- 1992-10-22 WO PCT/DE1992/000904 patent/WO1993007875A1/de not_active Ceased
-
1998
- 1998-03-11 GR GR980400515T patent/GR3026324T3/el unknown
Also Published As
| Publication number | Publication date |
|---|---|
| JPH07500585A (ja) | 1995-01-19 |
| PT100997A (pt) | 1994-01-31 |
| EP0609336A1 (de) | 1994-08-10 |
| CA2121838A1 (en) | 1993-04-29 |
| US5814301A (en) | 1998-09-29 |
| ATE162718T1 (de) | 1998-02-15 |
| EP0609336B1 (de) | 1998-01-28 |
| DE4135193C1 (https=) | 1993-03-11 |
| DK0609336T3 (da) | 1998-09-21 |
| ES2114570T3 (es) | 1998-06-01 |
| WO1993007875A1 (de) | 1993-04-29 |
| GR3026324T3 (en) | 1998-06-30 |
| DE59209175D1 (de) | 1998-03-05 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| PT100997B (pt) | Processo para preparacao de composicoes farmaceuticas uteis para a reducao ou o tratamento de pereturbacoes da microcirculacao provocadas pela administracao de meios de contraste para raios x, nmr ou ultrassons por incorporacao de derivados de prostaciclinas | |
| US5785950A (en) | Highly fluorinated, chloro-substituted organic compound-containing emulsions and methods of making and using them | |
| JP2006348301A (ja) | ６−メルカプト−シクロデキストリン誘導体：薬物誘導神経筋遮断回復薬 | |
| HRP980341A2 (en) | Pharmaceutical formulations containing voriconazole | |
| EP0153858A2 (en) | The therapeutic use of prostaglandins | |
| TWI251491B (en) | Pharmaceutical combinations | |
| JPH05504953A (ja) | 造影剤 | |
| CN104349780A (zh) | 含有吡罗昔康或其药学上可接受的盐和透明质酸或其药学上可接受的盐的稳定液体药学组合物及其制造方法 | |
| BR112015023481B1 (pt) | Projeto de perfil de liberação de fármaco de controle via composição de lipossomo em ambos os compartimentos aquosos e não-aquososreferência cruzada para requerimentos relacionados | |
| JP2020531538A5 (https=) | ||
| BR112017011258B1 (pt) | Suspensão aquosa de microvesículas enchidas com gás e kit farmacêutico | |
| JP3049366B2 (ja) | 造影剤 | |
| US5366722A (en) | Contrast media comprising a non-ionic contrast agent and sodium ions | |
| WO1999036065A1 (en) | Medicinal compositions | |
| US20030232884A1 (en) | New pharmaceutical formulation | |
| PT1515740E (pt) | Preparação líquida contendo oligopéptidos e ciclodextrina eterificada | |
| JP6048971B2 (ja) | 置換６−デオキシ−６−スルファニルシクロデキストリンを含む医薬組成物 | |
| JP2005515982A (ja) | ２−ヒドロキシプロピル−β−シクロデキストリンによるタキソールの包接錯体 | |
| BR112021014897A2 (pt) | Composto ou um sal farmaceuticamente aceitável do mesmo, e, composição farmacêutica | |
| TW201035091A (en) | 1,4-benzothiazepine-1-oxide derivatives and pharmaceutical composition using same | |
| JP2009096749A (ja) | コレステロール誘導体、リポソーム及びｘ線用造影剤 | |
| JPH02502379A (ja) | ５‐シアノ‐プロスタサイクリン誘導体のシクロデキストリンクラスレート化合物、および薬剤としてのその使用 | |
| PT1519756E (pt) | Utilização de complexos metálicos contendo perfluoroalquilo como agentes de contraste na imagiologia por ressonância magnética para a visualização de trombos intravasculares | |
| JP2002543175A (ja) | 造影剤 | |
| JPWO2007102562A1 (ja) | 新規抗血栓薬 |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| BB1A | Laying open of patent application |
Effective date: 19930701 |
|
| FG3A | Patent granted, date of granting |
Effective date: 19990730 |
|
| MM3A | Annulment or lapse |
Free format text: LAPSE DUE TO NON-PAYMENT OF FEES Effective date: 20010131 |