HRP20141137T1 - Polimorfni oblici macrocikliäśkog inhibitora hcv - Google Patents
Polimorfni oblici macrocikliäśkog inhibitora hcv Download PDFInfo
- Publication number
- HRP20141137T1 HRP20141137T1 HRP20141137AT HRP20141137T HRP20141137T1 HR P20141137 T1 HRP20141137 T1 HR P20141137T1 HR P20141137A T HRP20141137A T HR P20141137AT HR P20141137 T HRP20141137 T HR P20141137T HR P20141137 T1 HRP20141137 T1 HR P20141137T1
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- Croatia
- Prior art keywords
- compound
- formula
- mixture
- saturated
- crystalline
- Prior art date
Links
- 239000003112 inhibitor Substances 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims 31
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims 18
- 239000000203 mixture Substances 0.000 claims 17
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 claims 15
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims 12
- 229920006395 saturated elastomer Polymers 0.000 claims 11
- 239000012047 saturated solution Substances 0.000 claims 11
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims 9
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 9
- 238000000034 method Methods 0.000 claims 8
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 claims 7
- ARXJGSRGQADJSQ-UHFFFAOYSA-N 1-methoxypropan-2-ol Chemical compound COCC(C)O ARXJGSRGQADJSQ-UHFFFAOYSA-N 0.000 claims 6
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims 6
- BTANRVKWQNVYAZ-UHFFFAOYSA-N butan-2-ol Chemical compound CCC(C)O BTANRVKWQNVYAZ-UHFFFAOYSA-N 0.000 claims 6
- 238000000634 powder X-ray diffraction Methods 0.000 claims 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims 6
- 238000010438 heat treatment Methods 0.000 claims 5
- 239000000243 solution Substances 0.000 claims 5
- SYBYTAAJFKOIEJ-UHFFFAOYSA-N 3-Methylbutan-2-one Chemical compound CC(C)C(C)=O SYBYTAAJFKOIEJ-UHFFFAOYSA-N 0.000 claims 4
- 238000002329 infrared spectrum Methods 0.000 claims 4
- 238000002360 preparation method Methods 0.000 claims 4
- 239000002904 solvent Substances 0.000 claims 4
- 241000711549 Hepacivirus C Species 0.000 claims 3
- 238000002156 mixing Methods 0.000 claims 3
- 239000000825 pharmaceutical preparation Substances 0.000 claims 3
- 238000010992 reflux Methods 0.000 claims 3
- 239000000725 suspension Substances 0.000 claims 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims 2
- 230000001476 alcoholic effect Effects 0.000 claims 2
- 150000001298 alcohols Chemical class 0.000 claims 2
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 claims 2
- 238000001816 cooling Methods 0.000 claims 1
- 239000013078 crystal Substances 0.000 claims 1
- 239000003814 drug Substances 0.000 claims 1
- 229940079593 drug Drugs 0.000 claims 1
- 210000002257 embryonic structure Anatomy 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 238000010899 nucleation Methods 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- 239000007787 solid Substances 0.000 claims 1
- 230000002269 spontaneous effect Effects 0.000 claims 1
- 238000003756 stirring Methods 0.000 claims 1
Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/16—Drugs for disorders of the alimentary tract or the digestive system for liver or gallbladder disorders, e.g. hepatoprotective agents, cholagogues, litholytics
-
- 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
- A61P31/12—Antivirals
-
- 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
- A61P31/12—Antivirals
- A61P31/14—Antivirals for RNA viruses
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B2200/00—Indexing scheme relating to specific properties of organic compounds
- C07B2200/13—Crystalline forms, e.g. polymorphs
Claims (29)
1. Spoj sa formulom (I):
[image]
u krutom stanju naznačen time da je u kristalnom obliku.
2. Spoj prema zahtjevu 1 naznačen time da kristalni oblik ima uzorak difrakcije X-zraka na prahu koji ima pikove na 8.5°± 0.2°, 10.7°± 0.2°, 13.7°± 0.2°, 14.8°± 0.2° i 17.1°± 0.2° dva theta (Oblik I).
3. Spoj prema zahtjevu 2 naznačen time da kristalni oblik ima uzorak IR spektra koji ima pikove na 3405 ± 1 cm-1, 3066 ± 1 cm-1, 1517 ± 1 cm-1, 1427 ± 1 cm-1, 1301 ± 1 cm-1, 1285 ± 1 cm-1, 1149 ± 1 cm-1, 1132 ± 1 cm-1, 1111 ± 1 cm-1, 975 ± 1 cm-1, 956 ± 1 cm-1, i 800 ± 1 cm-1 (Oblik I).
4. Spoj prema zahtjevu 1 naznačen time da kristalni oblik ima uzorak difrakcije X-zraka na prahu koji ima pikove na 4.6°± 0.2°, 6.5°± 0.2°, 10.2°± 0.2°, 12.9°± 0.2° i 14.4°± 0.2 dva theta (Oblik II).
5. Spoj prema zahtjevu 4 naznačen time da kristalni oblik ima uzorak IR spektra koji ima pikove na 1592 cm-1 ± 1 cm-1 (Oblik II).
6. Spoj prema zahtjevu 1 naznačen time da kristalni oblik ima uzorak difrakcije X-zraka na prahu koji ima pikove na 6.5°± 0.2°, 9.8°± 0.2° i 17.8°± 0.2° dva theta (Oblik III).
7. Spoj prema zahtjevu 6 naznačen time da kristalni oblik ima uzorak IR spektra koji ima pikove na 3120 ±1 cm-1, 2870 ±1 cm-1, i 1063 cm-1 ±1 cm-1 (Oblik III).
8. Spoj prema zahtjevu 1 naznačen time da kristalni oblik ima uzorak difrakcije X-zraka na prahu koji ima pikove na 5.6°± 0.2°, 9.6°± 0.2°, 11.8°± 0.2°, 15.9°± 0.2° i 17.1°± 0.2° dva theta (Oblik IV).
9. Spoj prema zahtjevu 8 naznačen time da kristalni oblik ima uzorak IR spektra koji ima pikove na 1369 ±1 cm-1 i 846 ±1 cm-1 (Oblik IV).
10. Spoj prema zahtjevu 1 naznačen time da kristalni oblik ima uzorak difrakcije X-zraka na prahu koji ima pikove na 9.6° ± 0.2° i 19.0° ± 0.2° dva theta (Oblik V).
11. Spoj prema zahtjevu 1 naznačen time da kristalni oblik ima uzorak difrakcije X-zraka na prahu koji ima pikove na 4.4° ± 0.2°, 6.5° ± 0.2°, 9.9° ± 0.2°, 10.5° ± 0.2° i 12.9° ± 0.2° dva theta (Oblik VI).
12. Smjesa dva ili više kristalnih oblika spoja formule (I), naznačena time da su kristalni oblici odabrani od Oblika I prema zahtjevima 2-3, Oblika II prema zahtjevima 4-5, Oblika III prema zahtjevima 6-7, Oblika IV prema zahtjevima 8-9, Oblika V prema zahtjevu 10, te Oblika VI prema zahtjevu 11.
13. Smjesa prema zahtjevu 12, naznačena time da smjesa sadrži Oblik II i Oblik I spoja sa formulom (I).
14. Smjesa prema zahtjevu 12, naznačena time da smjesa sadrži Oblik III i Oblik II spoja sa formulom (I).
15. Smjesa jednog ili više kristalnih oblika spoja formule (I) i amorfnog oblika spoja formule (I), naznačena time da su kristalni oblici odabrani od Oblika I prema zahtjevima 2-3, Oblika II prema zahtjevima 4-5, Oblika III prema zahtjevima 6-7, Oblika IV prema zahtjevima 8-9, Oblika V prema zahtjevu 10, te Oblika VI prema zahtjevu 11.
16. Smjesa prema zahtjevu 15, naznačena time da smjesa sadrži Oblik II prema zahtjevima 4-5 i amorfni oblik spoja formule (I).
17. Postupak za dobivanje kristalnog oblika prema bilo kojem od patentnih zahtjeva 2-3 (Oblik I) naznačen time da sadrži:
a) otapanje spoja formule (I) u 1-butanolu ili 2-propanolu uz zagrijavanje na temperaturi refluksa otapala; te
b) omogućavanje spontanog hlađenja.
18. Postupak za dobivanje kristalnog oblika prema bilo kojem od patentnih zahtjeva 2-3 (Oblik I) naznačen time da sadrži:
- pripravu guste otopine Oblika II u alkoholnom otapalu odabranom od 2-propanola, etanola, 1-butanola, metanola, smjesi alkohola (kao što su metanol, etanol, propanol, izopropanol, 1-butanol, ili 2-butanol) i diklorometanu ili vodi, ili njihovoj smjesi, kod temperature refluksa alkoholnog otapala; ili
- pripravu guste otopine smjese Oblika I i Oblika II u otapalu odabranom od 2-propanola, metil izopropilketona (MIK), THF, acetonitrila, etanola, acetona, 1-metoksipropan-2-ola (1-M-2-P), metil etilketona (MEK), diklorometana, 1-butanol, metanola, smjese alkohola (kao što su metanol, etanol, propanol, izopropanol, 1-butanol, ili 2-butanol) i diklorometanu ili vodi, ili njihovoj smjesi, kod temperature od najmanje oko 30°C.
19. Postupak za dobivanje kristalnog oblika prema bilo kojem od patentnih zahtjeva 4-5 (Oblik II) naznačen time da sadrži:
pripravu suspenzije amorfnog oblika spoja formule (I) u izopropanolu;
miješanje suspenzije kod sobne temperature; i
zametanje suspenzije sa zametcima kristala Oblika II ili Oblika I.
20. Postupak za dobivanje kristalnog oblika prema bilo kojem od patentnih zahtjeva 4-5 (Oblik II) naznačen time da sadrži:
otapanje spoja formule (I) u 2-propanolu; te
držanje otopine iz koraka a) kod sobne temperature tijekom barem 1 dan, ili kod oko 0°C tijekom najmanje 4 sata.
21. Postupak za dobivanje kristalnog oblika prema bilo kojem od patentnih zahtjeva 6-7 (Oblik III) naznačen time da sadrži:
pripremanje zasićene ili gotovo zasićene otopine spoja formule (I) u acetonitrilu, te zasićene ili gotovo zasićene otopine spoja formule (I) u vodi;
zagrijavanje dviju zasićenih ili gotovo zasićenih otopina iz koraka a) najmanje na 40°C;
miješanje dviju zasićenih ili gotovo zasićenih otopina iz koraka b) uz volumni omjer 50/50.
22. Postupak za dobivanje kristalnog oblika prema bilo kojem od patentnih zahtjeva 8-9 (Oblik IV) naznačen time da sadrži:
pripremanje zasićene ili gotovo zasićene otopine spoja formule (I) u 1-metoksi-2-propanolu;
zagrijavanje zasićene ili gotovo zasićene otopine na temperaturi refluksa 1-metoksi-2-propanola;
miješanje zasićene ili gotovo zasićene otopine iz koraka b) s vodom uz volumni omjer 4/10.
23. Postupak za dobivanje kristalnog oblika prema zahtjevu 10 (Oblik V) naznačen time da sadrži:
pripremanje zasićene ili gotovo zasićene otopine spoja formule (I) u 2-butanonu, te zasićene ili gotovo zasićene otopine spoja formule (I) u vodi;
zagrijavanje dviju zasićenih ili gotovo zasićenih otopina iz koraka a) najmanje na 40°C;
miješanje dviju zasićenih ili gotovo zasićenih otopina iz koraka b) uz volumni omjer 50/50.
24. Postupak za dobivanje kristalnog oblika prema zahtjevu 11 (Oblik VI) naznačen time da sadrži:
pripravu guste otopine spoja formule (I) u vodi;
zagrijavanje guste otopine iz koraka a) najmanje kod sobne temperature tijekom barem 4 dana.
25. Farmaceutski pripravak naznačen time da sadrži kristalni oblik spoja formule (I), smjesu dva ili više kristalnih oblika spoja formule (I), te farmaceutski prihvatljivu pomoćnu tvar.
26. Farmaceutski pripravak prema zahtjevu 25 naznačen time da je oblik odabran od Oblika I, II, III, IV, V, i VI.
27. Spoj prema bilo kojem od patentnih zahtjeva 1-11 ili smjesa prema bilo kojem od patentnih zahtjeva 12-16 naznačen time da je za uporabu kao farmaceutski pripravak.
28. Spoj prema bilo kojem od patentnih zahtjeva 1-11 ili smjesa prema bilo kojem od patentnih zahtjeva 12-16 naznačen time da je za uporabu kod liječenja virusa hepatitisa C (HCV).
29. Uporaba spoja prema bilo kojem od patentnih zahtjeva 1-11 ili smjese prema bilo kojem od patentnih zahtjeva 12-16 naznačena time da je za proizvodnju lijeka za liječenje HCV.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP07101563 | 2007-02-01 | ||
| PCT/EP2008/051268 WO2008092954A2 (en) | 2007-02-01 | 2008-02-01 | Polymorphic forms of a macrocyclic inhibitor of hcv |
| EP08708575.9A EP2118098B1 (en) | 2007-02-01 | 2008-02-01 | Polymorphic forms of a macrocyclic inhibitor of hcv |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| HRP20141137T1 true HRP20141137T1 (hr) | 2015-01-30 |
Family
ID=38229348
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HRP20141137AT HRP20141137T1 (hr) | 2007-02-01 | 2014-11-24 | Polimorfni oblici macrocikliäśkog inhibitora hcv |
Country Status (25)
| Country | Link |
|---|---|
| US (1) | US8143402B2 (hr) |
| EP (1) | EP2118098B1 (hr) |
| JP (1) | JP5523110B2 (hr) |
| KR (1) | KR101580226B1 (hr) |
| CN (3) | CN105037347B (hr) |
| AR (2) | AR065136A1 (hr) |
| AU (1) | AU2008209696B2 (hr) |
| BR (1) | BRPI0806945A2 (hr) |
| CA (1) | CA2677170C (hr) |
| CL (1) | CL2008000321A1 (hr) |
| CY (1) | CY1116339T1 (hr) |
| DK (1) | DK2118098T3 (hr) |
| ES (1) | ES2524784T3 (hr) |
| HK (2) | HK1137438A1 (hr) |
| HR (1) | HRP20141137T1 (hr) |
| IL (1) | IL199215A (hr) |
| MX (1) | MX2009008275A (hr) |
| NZ (1) | NZ577568A (hr) |
| PL (1) | PL2118098T3 (hr) |
| PT (1) | PT2118098E (hr) |
| RU (1) | RU2533830C2 (hr) |
| SI (1) | SI2118098T1 (hr) |
| TW (1) | TWI423968B (hr) |
| WO (1) | WO2008092954A2 (hr) |
| ZA (1) | ZA200905377B (hr) |
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| MY140680A (en) | 2002-05-20 | 2010-01-15 | Bristol Myers Squibb Co | Hepatitis c virus inhibitors |
| PE20070211A1 (es) | 2005-07-29 | 2007-05-12 | Medivir Ab | Compuestos macrociclicos como inhibidores del virus de hepatitis c |
| US8207341B2 (en) | 2008-09-04 | 2012-06-26 | Bristol-Myers Squibb Company | Process or synthesizing substituted isoquinolines |
| UY32099A (es) | 2008-09-11 | 2010-04-30 | Enanta Pharm Inc | Inhibidores macrocíclicos de serina proteasas de hepatitis c |
| SG173772A1 (en) * | 2009-02-27 | 2011-09-29 | Ortho Mcneil Janssen Pharm | Amorphous salt of a macrocyclic inhibitor of hcv |
| TW201040181A (en) | 2009-04-08 | 2010-11-16 | Idenix Pharmaceuticals Inc | Macrocyclic serine protease inhibitors |
| WO2011017389A1 (en) | 2009-08-05 | 2011-02-10 | Idenix Pharmaceuticals, Inc. | Macrocyclic serine protease inhibitors useful against viral infections, particularly hcv |
| JP5833022B2 (ja) | 2010-01-27 | 2015-12-16 | エービー・ファーマ・リミテッド | Ｃ型肝炎ウィルス阻害剤としてのポリ複素環式化合物 |
| EP2658858A4 (en) | 2010-12-30 | 2014-06-25 | Enanta Pharm Inc | MACROCYCLIC INHIBITORS OF HEPATITIS C SERINE PROTEASE PHENANTHRIDINE |
| WO2012092409A2 (en) | 2010-12-30 | 2012-07-05 | Enanta Phararmaceuticals, Inc | Macrocyclic hepatitis c serine protease inhibitors |
| WO2012109398A1 (en) | 2011-02-10 | 2012-08-16 | Idenix Pharmaceuticals, Inc. | Macrocyclic serine protease inhibitors, pharmaceutical compositions thereof, and their use for treating hcv infections |
| US20140058116A1 (en) * | 2011-05-04 | 2014-02-27 | Ji Xie | Process for preparing inhibitors of the hepatitis c virus |
| US8957203B2 (en) | 2011-05-05 | 2015-02-17 | Bristol-Myers Squibb Company | Hepatitis C virus inhibitors |
| US10201584B1 (en) | 2011-05-17 | 2019-02-12 | Abbvie Inc. | Compositions and methods for treating HCV |
| US8691757B2 (en) | 2011-06-15 | 2014-04-08 | Bristol-Myers Squibb Company | Hepatitis C virus inhibitors |
| CA2857705A1 (en) | 2011-06-16 | 2012-12-20 | AB Pharma Ltd. | Macrocyclic heterocyclic compounds for inhibiting hepatitis c virus and preparation and use thereof |
| PE20142083A1 (es) * | 2011-09-16 | 2014-12-30 | Fovea Pharmaceuticals | Derivados de anilina, su preparacion y su aplicacion terapeutica |
| GB2515942A (en) | 2011-10-21 | 2015-01-07 | Abbvie Inc | Combination treatment (e.g. with ABT-072 or ABT-333) of DAAs for use in treating HCV |
| US8853176B2 (en) | 2011-10-21 | 2014-10-07 | Abbvie Inc. | Methods for treating HCV |
| US8466159B2 (en) | 2011-10-21 | 2013-06-18 | Abbvie Inc. | Methods for treating HCV |
| US8492386B2 (en) | 2011-10-21 | 2013-07-23 | Abbvie Inc. | Methods for treating HCV |
| PT2909205T (pt) | 2012-10-19 | 2017-02-06 | Bristol Myers Squibb Co | Derivados de carbamato de hexadecahidrociclopropa(e)pirrolo(1,2- a)(1,4)diazaciclopentadecinilo substituídos com 9-metilo como inibidores da protease não estrutural 3 (ns3) para o tratamento de infeções por vírus da hepatite c |
| US9643999B2 (en) | 2012-11-02 | 2017-05-09 | Bristol-Myers Squibb Company | Hepatitis C virus inhibitors |
| US9334279B2 (en) | 2012-11-02 | 2016-05-10 | Bristol-Myers Squibb Company | Hepatitis C virus inhibitors |
| US9598433B2 (en) | 2012-11-02 | 2017-03-21 | Bristol-Myers Squibb Company | Hepatitis C virus inhibitors |
| US9409943B2 (en) | 2012-11-05 | 2016-08-09 | Bristol-Myers Squibb Company | Hepatitis C virus inhibitors |
| JP6342922B2 (ja) | 2013-03-07 | 2018-06-13 | ブリストル−マイヤーズ スクイブ カンパニーＢｒｉｓｔｏｌ−Ｍｙｅｒｓ Ｓｑｕｉｂｂ Ｃｏｍｐａｎｙ | Ｃ型肝炎ウイルス阻害剤 |
| WO2015103490A1 (en) | 2014-01-03 | 2015-07-09 | Abbvie, Inc. | Solid antiviral dosage forms |
| WO2015109925A1 (zh) * | 2014-01-21 | 2015-07-30 | 杭州普晒医药科技有限公司 | 丙型肝炎药物的晶型及其制备方法、其药物组合物和用途 |
| WO2015180253A1 (zh) * | 2014-05-29 | 2015-12-03 | 杭州普晒医药科技有限公司 | 丙型肝炎药物的晶型及其制备方法、其药物组合物和用途 |
| CZ2015220A3 (cs) * | 2015-03-27 | 2016-10-05 | Zentiva, K.S. | Amorfní sůl makrocyklického inhibitoru viru hepatitidy C |
| WO2016177625A1 (en) | 2015-05-04 | 2016-11-10 | Sandoz Ag | Amorphous simeprevir potassium |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1771050A (zh) * | 2003-02-07 | 2006-05-10 | 益安药业 | 丙型肝炎丝氨酸蛋白酶的大环抑制剂 |
| JP4525982B2 (ja) * | 2003-09-26 | 2010-08-18 | シェーリング コーポレイション | Ｃ型肝炎ウイルスのｎｓ３セリンプロテアーゼの大環状インヒビター |
| RS20060259A (en) * | 2003-10-14 | 2008-08-07 | Intermune Inc., | Macrocyclic carboxylic acids and acylsulfonamides as inhibitors of hcv replication |
| AR048401A1 (es) * | 2004-01-30 | 2006-04-26 | Medivir Ab | Inhibidores de la serina-proteasa ns3 del vhc |
| PE20070211A1 (es) * | 2005-07-29 | 2007-05-12 | Medivir Ab | Compuestos macrociclicos como inhibidores del virus de hepatitis c |
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