HRP20191525T1 - Inhibitori replikacije virusa influence - Google Patents
Inhibitori replikacije virusa influence Download PDFInfo
- Publication number
- HRP20191525T1 HRP20191525T1 HRP20191525T HRP20191525T1 HR P20191525 T1 HRP20191525 T1 HR P20191525T1 HR P20191525 T HRP20191525 T HR P20191525T HR P20191525 T1 HRP20191525 T1 HR P20191525T1
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- Croatia
- Prior art keywords
- polymorphic form
- methyl
- acetate
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- compound
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- 241000712461 unidentified influenza virus Species 0.000 title claims 3
- 230000010076 replication Effects 0.000 title claims 2
- 239000003112 inhibitor Substances 0.000 title 1
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims 12
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims 10
- 238000000034 method Methods 0.000 claims 9
- 150000001875 compounds Chemical class 0.000 claims 8
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 claims 8
- 239000002904 solvent Substances 0.000 claims 7
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 claims 6
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims 6
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 claims 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims 6
- BTANRVKWQNVYAZ-UHFFFAOYSA-N butan-2-ol Chemical compound CCC(C)O BTANRVKWQNVYAZ-UHFFFAOYSA-N 0.000 claims 6
- 239000003960 organic solvent Substances 0.000 claims 5
- AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical compound CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 claims 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims 4
- 229940022682 acetone Drugs 0.000 claims 4
- 206010022000 influenza Diseases 0.000 claims 4
- PHTQWCKDNZKARW-UHFFFAOYSA-N isoamylol Chemical compound CC(C)CCO PHTQWCKDNZKARW-UHFFFAOYSA-N 0.000 claims 4
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 claims 4
- 229960004592 isopropanol Drugs 0.000 claims 4
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims 3
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 claims 3
- 239000003443 antiviral agent Substances 0.000 claims 3
- GJRQTCIYDGXPES-UHFFFAOYSA-N iso-butyl acetate Natural products CC(C)COC(C)=O GJRQTCIYDGXPES-UHFFFAOYSA-N 0.000 claims 3
- FGKJLKRYENPLQH-UHFFFAOYSA-M isocaproate Chemical compound CC(C)CCC([O-])=O FGKJLKRYENPLQH-UHFFFAOYSA-M 0.000 claims 3
- OQAGVSWESNCJJT-UHFFFAOYSA-N isovaleric acid methyl ester Natural products COC(=O)CC(C)C OQAGVSWESNCJJT-UHFFFAOYSA-N 0.000 claims 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims 3
- 238000000634 powder X-ray diffraction Methods 0.000 claims 3
- 150000003839 salts Chemical class 0.000 claims 3
- CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical compound C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 claims 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims 3
- 229940044613 1-propanol Drugs 0.000 claims 2
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 claims 2
- QQZOPKMRPOGIEB-UHFFFAOYSA-N 2-Oxohexane Chemical compound CCCCC(C)=O QQZOPKMRPOGIEB-UHFFFAOYSA-N 0.000 claims 2
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 claims 2
- 229940093475 2-ethoxyethanol Drugs 0.000 claims 2
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 claims 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims 2
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 claims 2
- ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 claims 2
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 claims 2
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 claims 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 claims 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 claims 2
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 claims 2
- KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 claims 2
- RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 claims 2
- 239000007864 aqueous solution Substances 0.000 claims 2
- 229940043232 butyl acetate Drugs 0.000 claims 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 claims 2
- RWGFKTVRMDUZSP-UHFFFAOYSA-N cumene Chemical compound CC(C)C1=CC=CC=C1 RWGFKTVRMDUZSP-UHFFFAOYSA-N 0.000 claims 2
- 239000003814 drug Substances 0.000 claims 2
- 230000000694 effects Effects 0.000 claims 2
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 claims 2
- JMMWKPVZQRWMSS-UHFFFAOYSA-N isopropanol acetate Natural products CC(C)OC(C)=O JMMWKPVZQRWMSS-UHFFFAOYSA-N 0.000 claims 2
- 229940011051 isopropyl acetate Drugs 0.000 claims 2
- GWYFCOCPABKNJV-UHFFFAOYSA-N isovaleric acid Chemical compound CC(C)CC(O)=O GWYFCOCPABKNJV-UHFFFAOYSA-N 0.000 claims 2
- 229940043265 methyl isobutyl ketone Drugs 0.000 claims 2
- UAEPNZWRGJTJPN-UHFFFAOYSA-N methylcyclohexane Chemical compound CC1CCCCC1 UAEPNZWRGJTJPN-UHFFFAOYSA-N 0.000 claims 2
- 229940032007 methylethyl ketone Drugs 0.000 claims 2
- YKYONYBAUNKHLG-UHFFFAOYSA-N n-Propyl acetate Natural products CCCOC(C)=O YKYONYBAUNKHLG-UHFFFAOYSA-N 0.000 claims 2
- 229940090181 propyl acetate Drugs 0.000 claims 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims 2
- 238000000371 solid-state nuclear magnetic resonance spectroscopy Methods 0.000 claims 2
- 238000001228 spectrum Methods 0.000 claims 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims 2
- 229940124597 therapeutic agent Drugs 0.000 claims 2
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 claims 2
- 239000008096 xylene Substances 0.000 claims 2
- KFUSEUYYWQURPO-UHFFFAOYSA-N 1,2-dichloroethene Chemical compound ClC=CCl KFUSEUYYWQURPO-UHFFFAOYSA-N 0.000 claims 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 claims 1
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 claims 1
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 claims 1
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 claims 1
- 229940123424 Neuraminidase inhibitor Drugs 0.000 claims 1
- 229940123066 Polymerase inhibitor Drugs 0.000 claims 1
- XSTXAVWGXDQKEL-UHFFFAOYSA-N Trichloroethylene Chemical compound ClC=C(Cl)Cl XSTXAVWGXDQKEL-UHFFFAOYSA-N 0.000 claims 1
- 241000700605 Viruses Species 0.000 claims 1
- 229960000583 acetic acid Drugs 0.000 claims 1
- 239000012472 biological sample Substances 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- WBJINCZRORDGAQ-UHFFFAOYSA-N formic acid ethyl ester Natural products CCOC=O WBJINCZRORDGAQ-UHFFFAOYSA-N 0.000 claims 1
- 238000000338 in vitro Methods 0.000 claims 1
- 208000015181 infectious disease Diseases 0.000 claims 1
- 230000002401 inhibitory effect Effects 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 claims 1
- GYNNXHKOJHMOHS-UHFFFAOYSA-N methyl-cycloheptane Natural products CC1CCCCCC1 GYNNXHKOJHMOHS-UHFFFAOYSA-N 0.000 claims 1
- LYGJENNIWJXYER-UHFFFAOYSA-N nitromethane Chemical compound C[N+]([O-])=O LYGJENNIWJXYER-UHFFFAOYSA-N 0.000 claims 1
- VSZGPKBBMSAYNT-RRFJBIMHSA-N oseltamivir Chemical compound CCOC(=O)C1=C[C@@H](OC(CC)CC)[C@H](NC(C)=O)[C@@H](N)C1 VSZGPKBBMSAYNT-RRFJBIMHSA-N 0.000 claims 1
- 229960003752 oseltamivir Drugs 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- 239000000825 pharmaceutical preparation Substances 0.000 claims 1
- 239000000523 sample Substances 0.000 claims 1
- 239000002911 sialidase inhibitor Substances 0.000 claims 1
- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 claims 1
- 229940074411 xylene Drugs 0.000 claims 1
- 229960001028 zanamivir Drugs 0.000 claims 1
- ARAIBEBZBOPLMB-UFGQHTETSA-N zanamivir Chemical compound CC(=O)N[C@@H]1[C@@H](N=C(N)N)C=C(C(O)=O)O[C@H]1[C@H](O)[C@H](O)CO ARAIBEBZBOPLMB-UFGQHTETSA-N 0.000 claims 1
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- A61K31/21—Esters, e.g. nitroglycerine, selenocyanates
- A61K31/215—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids
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- A61K31/33—Heterocyclic compounds
- A61K31/335—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin
- A61K31/35—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having six-membered rings with one oxygen as the only ring hetero atom
- A61K31/351—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having six-membered rings with one oxygen as the only ring hetero atom not condensed with another ring
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- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/4353—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom ortho- or peri-condensed with heterocyclic ring systems
- A61K31/437—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom ortho- or peri-condensed with heterocyclic ring systems the heterocyclic ring system containing a five-membered ring having nitrogen as a ring hetero atom, e.g. indolizine, beta-carboline
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- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
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- A61K31/505—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
- A61K31/506—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim not condensed and containing further heterocyclic rings
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- A61K45/00—Medicinal preparations containing active ingredients not provided for in groups A61K31/00 - A61K41/00
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C309/00—Sulfonic acids; Halides, esters, or anhydrides thereof
- C07C309/01—Sulfonic acids
- C07C309/28—Sulfonic acids having sulfo groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
- C07C309/29—Sulfonic acids having sulfo groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton of non-condensed six-membered aromatic rings
- C07C309/30—Sulfonic acids having sulfo groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton of non-condensed six-membered aromatic rings of six-membered aromatic rings substituted by alkyl groups
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- C07—ORGANIC CHEMISTRY
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- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
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- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
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- Nitrogen Condensed Heterocyclic Rings (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
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Claims (24)
1. Polimorfni oblik Spoja (1), gdje Spoj (1) prikazuje sljedeća strukturna formula:
,
te gdje je polimorfni oblik kristalna sol s HCl hemihidrata Spoja (1), gdje je navedeni polimorfni oblik dodatno naznačen time što ima jedan ili više maksimuma koji odgovaraju vrijednostima 2θ izmjerenim u stupnjevima od 10,5 ± 0,2, 5,2 ± 0,2, 7,4 ± 0,2, te 18,9 ± 0,2 u uzorku difrakcije rendgenskih zraka na prahu.
2. Polimorfni oblik u skladu s patentnim zahtjevom 1, gdje je polimorfni oblik dodatno naznačen time što ima jedan ili više maksimuma koji odgovaraju vrijednostima 2θ izmjerenim u stupnjevima od 25,2 ± 0,2, 16,5 ± 0,2, 18,1 ± 0,2, te 23,0 ± 0,2 u uzorku difrakcije rendgenskih zraka na prahu.
3. Polimorfni oblik u skladu s patentnim zahtjevom 1 ili 2, gdje je polimorfni oblik dodatno naznačen time što ima jedan ili više maksimuma koji odgovaraju 29,2 ± 0,3 ppm, 107,0 ± 0,3 ppm, 114,0 ± 0,3 ppm, te 150,7 ± 0,3 ppm u C13 SSNMR spektru.
4. Polimorfni oblik u skladu s patentnim zahtjevom 3, gdje je polimorfni oblik dodatno naznačen time što ima jedan ili više maksimuma koji odgovaraju 22,1 ± 0,3 ppm, 24,6 ± 0,3 ppm, 47,7 ± 0,3 ppm, te 54,8 ± 0,3 ppm u C13 SSNMR spektru.
5. Farmaceutski pripravak, naznačen time što sadrži polimorfni oblik u skladu s patentnim zahtjevom 1 i najmanje jedan farmaceutski prihvatljivi nosač ili pomoćnu tvar.
6. Postupak smanjivanja količine ili inhibiranja replikacije virusa influence u biološkom uzorku in vitro, što uključuje primjenu na uzorku djelotvorne količine polimorfnog oblika Spoja (1) u skladu s bilo kojim od patentnih zahtjeva 1-4.
7. Postupak u skladu s patentnim zahtjevom 6, naznačen time što dodatno uključuje suprimjenu jednog ili više dodatnih terapijskih sredstava.
8. Postupak u skladu s patentnim zahtjevom 7, naznačen time što dodatna terapijska sredstva uključuju protuvirusni lijek.
9. Postupak u skladu s patentnim zahtjevom 8, naznačen time što je protuvirusni lijek inhibitor neuraminidaze kojeg se bira između oseltamivira ili zanamivira.
10. Postupak u skladu s patentnim zahtjevom 8, naznačen time što je protuvirusni lijek inhibitor polimeraze kojeg se bira od flavipiravira.
11. Postupak u skladu s bilo kojim od patentnih zahtjeva 6-10, naznačen time što su virusi influence virusi influence tip A.
12. Postupak priprave kristalne soli s HCl hemihidrata Spoja (1), gdje je navedena sol dodatno naznačena time što ima jedan ili više maksimuma koji odgovaraju vrijednostima 2θ izmjerenim u stupnjevima od 10,5 ± 0,2, 5,2 ± 0,2, 7,4 ± 0,2, te 18,9 ± 0,2 u uzorku difrakcije rendgenskih zraka na prahu, gdje Spoj (1) prikazuje sljedeća strukturna formula:
,
koji se sastoji u:
miješanju HCl sa Spojem (1) u sustavu otapala koji sadrži vodu i jedno ili više organskih otapala, gdje sustav otapala ima aktivitet vode od 0,05-0,85.
13. Postupak u skladu s patentnim zahtjevom 12, naznačen time što sustav otapala sadrži jedno ili više organskih otapala koja se bira između klorbenzena, cikloheksana, 1,2-dikloretena, diklormetana, 1,2-dimetoksietana, N,N-dimetilacetamida, N,N-dimetilformamida, 1,4-dioksana, 2-etoksietanola, formamida, heksana, 2-metoksietanola, metil-butil-ketona, metilcikloheksana, N-metilpirolidona, nitrometana, piridina, sulfolana, tetrahidrofurana (THF), tetralina, toluena, 1,1,2-trikloretena i ksilena, octene kiseline, acetona, anisola, 1-butanola, 2-butanola, butil-acetata, tert-butilmetil-etera, kumena, heptana, izobutil-acetata, izopropil-acetata, metil-acetata, 3-metil-1-butanola, metil-etil-ketona, metil-izobutil-ketona, 2-metil-1-propanola, etil-acetata, etil-etera, etil-formijata, pentana, 1-pentanola, 1-propanola, 2-propanola, propil-acetata, ili bilo koje njihove kombinacije; ili gdje sustav otapala sadrži jedno ili više organskih otapala koja se bira između 2-etoksietanola, etilen-glikola, metanola, 2-metoksietanola, 1-butanola, 2-butanola, 3-metil-1-butanola, 2-metil-1-propanola, etanola, 1-pentanola, 1-propanola, 2-propanola, metil-butil-ketona, acetona, metil-etil-ketona, metil-izobutil-ketona, butil-acetata, izobutil-acetata, izopropil-acetata, metil-acetata, etil-acetata, propil-acetata, piridina, toluena, ksilena, ili bilo koje njihove kombinacije; ili gdje sustav otapala sadrži jedno ili više organskih otapala koja se bira između acetona, n-propanola, izopropanola, iso-butil-acetata, octene kiseline, ili bilo koje njihove kombinacije; ili gdje sustav otapala sadrži jedno ili više organskih otapala koja se bira između acetona ili izopropanola.
14. Postupak u skladu s patentnim zahtjevom 13, naznačen time što sustav otapala ima vrijednost aktiviteta vode od 0,4 do 0,6.
15. Postupak u skladu s patentnim zahtjevom 13, naznačen time što se HCl dodaje kao vodenu otopinu s 30%, težinski, do 40%, težinski, HCl prema težini vodene otopine.
16. Polimorfni oblik Spoja (1) u skladu s patentnim zahtjevom 1, kojeg prikazuje sljedeća strukturna formula
,
naznačen time što je namijenjen upotrebi u liječenju infekcije influencom, gdje se navedeni polimorfni oblik primjenjuje na subjektu u količini doze od 100 mg do 1600 mg, te gdje se količinu doze primjenjuje jednom, dva puta ili tri puta dnevno.
17. Polimorfni oblik namijenjen upotrebi u skladu s patentnim zahtjevom 16, naznačen time što je količina doze 300 mg do 1600 mg.
18. Polimorfni oblik namijenjen upotrebi u skladu s patentnim zahtjevom 17, naznačen time što je količina doze 600 mg do 1200 mg.
19. Polimorfni oblik namijenjen upotrebi u skladu s patentnim zahtjevom 18, naznačen time što se dozu primjenjuje jednom dnevno.
20. Polimorfni oblik namijenjen upotrebi u skladu s patentnim zahtjevom 17, naznačen time što je količina doze 300 mg do 900 mg.
21. Polimorfni oblik namijenjen upotrebi u skladu s patentnim zahtjevom 20, naznačen time što se dozu primjenjuje dva puta dnevno.
22. Polimorfni oblik namijenjen upotrebi u skladu s bilo kojim od patentnih zahtjeva 16-21, naznačen time što je trajanje liječenja 3 dana do 14 dana.
23. Polimorfni oblik namijenjen upotrebi u skladu s bilo kojim od patentnih zahtjeva 16-22, naznačen time što se početnu količinu doze od 600 mg do 1600 mg primjenjuje na subjektu 1. dana, a količinu doze od 400 mg do 1200 mg se primjenjuje na subjektu tijekom ostatka trajanja liječenja.
24. Polimorfni oblik namijenjen upotrebi u skladu s bilo kojim od patentnih zahtjeva 16-23, naznačen time što je infekcija influencom infekcija influencom tip A.
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