HRP20110194T1 - Ciklopropil fuzionirani indolobenzazepini kao inhibitori hcv ns5b - Google Patents
Ciklopropil fuzionirani indolobenzazepini kao inhibitori hcv ns5b Download PDFInfo
- Publication number
- HRP20110194T1 HRP20110194T1 HR20110194T HRP20110194T HRP20110194T1 HR P20110194 T1 HRP20110194 T1 HR P20110194T1 HR 20110194 T HR20110194 T HR 20110194T HR P20110194 T HRP20110194 T HR P20110194T HR P20110194 T1 HRP20110194 T1 HR P20110194T1
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- Croatia
- Prior art keywords
- alkyl
- hcv
- image
- inhibitors
- hydrogen
- Prior art date
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- 239000003112 inhibitor Substances 0.000 title claims 7
- JYGUARFTLQSWDG-UHFFFAOYSA-N 3,12-diazatetracyclo[9.7.0.02,8.013,18]octadeca-1,3,5,7,9,11,13,15,17-nonaene Chemical compound C1=CC=NC2=C3C4=CC=CC=C4N=C3C=CC2=C1 JYGUARFTLQSWDG-UHFFFAOYSA-N 0.000 title 1
- 101710112514 Host translation inhibitor 5b Proteins 0.000 title 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 title 1
- 125000000217 alkyl group Chemical group 0.000 claims abstract 26
- 150000001875 compounds Chemical class 0.000 claims abstract 23
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract 17
- 239000001257 hydrogen Substances 0.000 claims abstract 17
- 125000000753 cycloalkyl group Chemical group 0.000 claims abstract 12
- -1 hydroxy, benzyloxy Chemical group 0.000 claims abstract 9
- 150000003839 salts Chemical class 0.000 claims abstract 9
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims abstract 6
- 125000000547 substituted alkyl group Chemical group 0.000 claims abstract 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract 5
- 125000003342 alkenyl group Chemical group 0.000 claims abstract 5
- 125000003545 alkoxy group Chemical group 0.000 claims abstract 5
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims abstract 4
- 125000004438 haloalkoxy group Chemical group 0.000 claims abstract 4
- 125000004193 piperazinyl group Chemical group 0.000 claims abstract 4
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims abstract 3
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims abstract 3
- 125000002393 azetidinyl group Chemical group 0.000 claims abstract 3
- 125000001475 halogen functional group Chemical group 0.000 claims abstract 3
- 125000002757 morpholinyl group Chemical group 0.000 claims abstract 3
- 125000003386 piperidinyl group Chemical group 0.000 claims abstract 3
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims abstract 3
- 125000004568 thiomorpholinyl group Chemical group 0.000 claims abstract 3
- 125000003282 alkyl amino group Chemical group 0.000 claims abstract 2
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims abstract 2
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract 2
- 125000006254 cycloalkyl carbonyl group Chemical group 0.000 claims abstract 2
- 125000001188 haloalkyl group Chemical group 0.000 claims abstract 2
- 125000004692 haloalkylcarbonyl group Chemical group 0.000 claims abstract 2
- 150000002431 hydrogen Chemical class 0.000 claims 6
- 239000012268 protein inhibitor Substances 0.000 claims 5
- 229940121649 protein inhibitor Drugs 0.000 claims 5
- 239000000203 mixture Substances 0.000 claims 4
- 108010036941 Cyclosporins Proteins 0.000 claims 2
- 229940122750 HCV entry inhibitor Drugs 0.000 claims 2
- 229940124683 HCV polymerase inhibitor Drugs 0.000 claims 2
- 102000014150 Interferons Human genes 0.000 claims 2
- 108010050904 Interferons Proteins 0.000 claims 2
- 102000015696 Interleukins Human genes 0.000 claims 2
- 108010063738 Interleukins Proteins 0.000 claims 2
- 108060004795 Methyltransferase Proteins 0.000 claims 2
- 101800001019 Non-structural protein 4B Proteins 0.000 claims 2
- 101800001014 Non-structural protein 5A Proteins 0.000 claims 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 2
- 125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 claims 2
- 229930182912 cyclosporin Natural products 0.000 claims 2
- 239000003966 growth inhibitor Substances 0.000 claims 2
- 108700008776 hepatitis C virus NS-5 Proteins 0.000 claims 2
- 229940047124 interferons Drugs 0.000 claims 2
- 229940047122 interleukins Drugs 0.000 claims 2
- 239000003475 metalloproteinase inhibitor Substances 0.000 claims 2
- UYWQUFXKFGHYNT-UHFFFAOYSA-N phenylmethyl ester of formic acid Natural products O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 0.000 claims 2
- 125000004076 pyridyl group Chemical group 0.000 claims 2
- 230000010076 replication Effects 0.000 claims 2
- 239000003001 serine protease inhibitor Substances 0.000 claims 2
- 230000001225 therapeutic effect Effects 0.000 claims 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical group Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims 1
- 125000004663 dialkyl amino group Chemical group 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 208000010710 hepatitis C virus infection Diseases 0.000 claims 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 claims 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 claims 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D519/00—Heterocyclic compounds containing more than one system of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring system not provided for in groups C07D453/00 or C07D455/00
-
- 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
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/55—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having seven-membered rings, e.g. azelastine, pentylenetetrazole
-
- 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
-
- 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
Abstract
Spoj formule Igdje: R1 je CO2R5 ili CONR6R7;R2 jeili R3 je vodik, halo, alkil, alkenil, hidroksi, benziloksi, alkoksi ili haloalkoksi; R4 je cikloalkil; R5 je vodik ili alkil; R6 je vodik, alkil, alkilSO2, cikloalkilSO2, haloalkilSO2, (R9)2NSO2 ili (R10)SO2;R7 je vodik ili alkil; R8 je vodik, alkil, cikloalkil, (cikloalkil)alkil, alkilkarbonil, cikloalkilkarbonil, haloalkilkarbonil, alkoksikarbonil, alkilSO2, cikloalkilSO2, haloalkilSO2, aminokarbonil, (alkilamino)karbonil, (dialkilamino)karbonil, benzil, benziloksikarbonil ili piridinil; R9 je vodik, alkil ili cikloalkil; iR10 je azetidinil, pirolidinil, piperidinil, piperazinil, morfolinil, tiomorfolinil, homopiperidinil ili homomorfolinil i supstituiran s 0-3 alkil supstituentima; pri čemu alkil predstavlja ravnu ili razgranatu alkilnu skupinu sastavljenu od 1 do 6 ugljika; alkenil predstavlja ravnu ili razgranatu alkilnu skupinu sastavljenu od 2 do 6 ugljika s barem jednom dvostrukom vezom; cikloalkil predstavlja sustav monocikličkog prstena sastavljenog od 3 do 7 ugljika; alkoksi i drugi pojmovi sa supstituiranom alkilnom skupinom obuhvaćaju ravne i razgranate izomere sastavljene od 1 do 6 atoma ugljika za alkilnu skupinu; haloalkil i haloalkoksi obuhvaćaju sve halogenirane izomere monohalo supstituiranog alkila do perhalo supstituiranog alkila; ili njegova farmaceutski prihvatljiva sol. Patent sadrži još 18 patentnih zahtjeva.
Claims (19)
1. Spoj formule I
[image]
gdje:
R1 je CO2R5 ili CONR6R7;
R2 je
[image]
ili
[image]
R3 je vodik, halo, alkil, alkenil, hidroksi, benziloksi, alkoksi ili haloalkoksi;
R4 je cikloalkil;
R5 je vodik ili alkil;
R6 je vodik, alkil, alkilSO2, cikloalkilSO2, haloalkilSO2, (R9)2NSO2 ili (R10)SO2;
R7 je vodik ili alkil;
R8 je vodik, alkil, cikloalkil, (cikloalkil)alkil, alkilkarbonil, cikloalkilkarbonil, haloalkilkarbonil, alkoksikarbonil, alkilSO2, cikloalkilSO2, haloalkilSO2, aminokarbonil, (alkilamino)karbonil, (dialkilamino)karbonil, benzil, benziloksikarbonil ili piridinil;
R9 je vodik, alkil ili cikloalkil; i
R10 je azetidinil, pirolidinil, piperidinil, piperazinil, morfolinil, tiomorfolinil, homopiperidinil ili homomorfolinil i supstituiran s 0-3 alkil supstituentima;
pri čemu alkil predstavlja ravnu ili razgranatu alkilnu skupinu sastavljenu od 1 do 6 ugljika; alkenil predstavlja ravnu ili razgranatu alkilnu skupinu sastavljenu od 2 do 6 ugljika s barem jednom dvostrukom vezom; cikloalkil predstavlja sustav monocikličkog prstena sastavljenog od 3 do 7 ugljika; alkoksi i drugi pojmovi sa supstituiranom alkilnom skupinom obuhvaćaju ravne i razgranate izomere sastavljene od 1 do 6 atoma ugljika za alkilnu skupinu; haloalkil i haloalkoksi obuhvaćaju sve halogenirane izomere monohalo supstituiranog alkila do perhalo supstituiranog alkila;
ili njegova farmaceutski prihvatljiva sol.
2. Spoj prema zahtjevu 1, naznačen time što:
R3 je vodik, halo, alkil, alkenil, hidroksi, benziloksi ili alkoksi;
R8 je vodik, alkil, cikloalkil, (cikloalkil)alkil, alkilkarbonil, alkoksikarbonil, benzil, benziloksikarbonil ili piridinil;
R9 je vodik ili alkil; i
R10 je azetidinil, pirolidinil, piperidinil, piperazinil, N-(alkil)piperazinil, morfolinil, tiomorfolinil, homopiperidinil ili homomorfolinil.
3. Spoj prema zahtjevu 1, naznačen time što R1 je CONR6R7; R6 je alkilSO2, cikloalkilSO2, haloalkilSO2, (R9)2NSO2 ili (R10)SO2; i R7 je vodik.
4. Spoj prema zahtjevu 1, naznačen time što R3 je vodik.
5. Spoj prema zahtjevu 1, naznačen time što R3 je metoksi.
6. Spoj prema zahtjevu 1, naznačen time što R4 je cikloheksil.
7. Spoj prema zahtjevu 1, naznačen time što R6 je alkilSO2, (R9)2NSO2 ili (R10)SO2.
8. Spoj prema zahtjevu 1, naznačen time što ima sljedeću stereokemiju.
[image]
9. Spoj prema zahtjevu 1, naznačen time što ima sljedeću stereokemiju.
[image]
10. Spoj prema zahtjevu 1, naznačen time što se izabire iz skupine koja obuhvaća
[image]
[image]
[image]
[image]
[image]
[image]
[image]
[image]
[image]
i
[image]
ili njegova farmaceutski prihvatljiva sol.
11. Spoj prema zahtjevu 1
[image]
ili njegova farmaceutski prihvatljiva sol.
12. Spoj prema zahtjevu 11, naznačen time što je sol klorovodik.
13. Spoj prema zahtjevu 1
[image]
ili njegova farmaceutski prihvatljiva sol.
14. Smjesa koja sadrži spoj formule 1, ili njegovu farmaceutski prihvatljivu sol, i farmaceutski prihvatljivi nosač.
15. Smjesa prema zahtjevu 14, naznačena time što dalje sadrži barem jedan dodatni spoj koji ima terapijske koristi za HCV, pri čemu se spoj odabire iz skupine koja obuhvaća interferone, ciklosporine, interleukine, inhibitore metaloproteaze HCV-a, inhibitore serin proteaze HCV-a, inhibitore polimeraze HCV-a, inhibitore helikaze HCV-a, inhibitore NS4B proteina HCV-a, inhibitore ulaska HCV-a, inhibitore razvoja HCV-a, inhibitore izlaska HCV-a, inhibitore NS5A proteina HCV-a, inhibitore NS5B proteina HCV-a i inhibitore replikacije HCV-a.
16. Smjesa prema zahtjevu 14, naznačena time što je spoj prema zahtjevu 1
[image]
ili njegova farmaceutski prihvatljiva sol.
17. Smjesa prema zahtjevu 15, naznačena time što je spoj prema zahtjevu 1
[image]
ili njegova farmaceutski prihvatljiva sol.
18. Spoj prema bilo kojem od zahtjeva 1 do 13, naznačen time što se koristi u postupku liječenja zaraze virusom hepatitisa C.
19. Spoj prema zahtjevu 18, naznačen time što dalje obuhvaća uporabu barem jednog dodatnog spoja koji ima terapijske koristi za HCV, pri čemu se spoj odabire iz skupine koja obuhvaća interferone, ciklosporine, interleukine, inhibitore metaloproteaze HCV-a, inhibitore serin proteaze HCV-a, inhibitore polimeraze HCV-a, inhibitore helikaze HCV-a, inhibitore NS4B proteina HCV-a, inhibitore ulaska HCV-a, inhibitore razvoja HCV-a, inhibitore izlaska HCV-a, inhibitore NS5A proteina HCV-a, inhibitore NS5B proteina HCV-a i inhibitore replikacije HCV-a
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US80112506P | 2006-05-17 | 2006-05-17 | |
| US80200506P | 2006-05-19 | 2006-05-19 | |
| US85208406P | 2006-10-16 | 2006-10-16 | |
| US89475707P | 2007-03-14 | 2007-03-14 | |
| PCT/US2007/068209 WO2007136982A1 (en) | 2006-05-17 | 2007-05-04 | Cyclopropyl fused indolobenzazepine hcv ns5b inhibitors |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| HRP20110194T1 true HRP20110194T1 (hr) | 2011-04-30 |
Family
ID=38512732
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HR20110194T HRP20110194T1 (hr) | 2006-05-17 | 2011-03-16 | Ciklopropil fuzionirani indolobenzazepini kao inhibitori hcv ns5b |
Country Status (25)
| Country | Link |
|---|---|
| US (1) | US7456166B2 (hr) |
| EP (1) | EP2024375B1 (hr) |
| JP (1) | JP5284952B2 (hr) |
| KR (1) | KR101417145B1 (hr) |
| AR (1) | AR061008A1 (hr) |
| AT (1) | ATE501156T1 (hr) |
| AU (1) | AU2007253998B2 (hr) |
| BR (1) | BRPI0711821A2 (hr) |
| CA (1) | CA2651690C (hr) |
| CY (1) | CY1111526T1 (hr) |
| DE (1) | DE602007013036D1 (hr) |
| DK (1) | DK2024375T3 (hr) |
| EA (1) | EA015286B1 (hr) |
| HK (1) | HK1122814A1 (hr) |
| HR (1) | HRP20110194T1 (hr) |
| IL (1) | IL195025A (hr) |
| MX (1) | MX2008014435A (hr) |
| NO (1) | NO341663B1 (hr) |
| NZ (1) | NZ572555A (hr) |
| PE (1) | PE20080070A1 (hr) |
| PL (1) | PL2024375T3 (hr) |
| SI (1) | SI2024375T1 (hr) |
| TW (1) | TWI401244B (hr) |
| WO (1) | WO2007136982A1 (hr) |
| ZA (1) | ZA200809548B (hr) |
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| PT1719773E (pt) | 2004-02-24 | 2009-06-03 | Japan Tobacco Inc | Compostos heterotetracíclicos fundidos e a sua utilização como inibidores da polimerase do hcv |
| US7348425B2 (en) * | 2004-08-09 | 2008-03-25 | Bristol-Myers Squibb Company | Inhibitors of HCV replication |
| US7153848B2 (en) * | 2004-08-09 | 2006-12-26 | Bristol-Myers Squibb Company | Inhibitors of HCV replication |
| WO2006040039A1 (de) | 2004-10-13 | 2006-04-20 | Merck Patent Gmbh | Als kinaseinhibitoren geeignete derivate des n, n ´ -diphenylharnstoffs |
| CA2585113A1 (en) * | 2004-10-26 | 2006-05-04 | Istituto Di Ricerche Di Biologia Molecolare P Angeletti Spa | Tetracyclic indole derivatives as antiviral agents |
| GB0518390D0 (en) | 2005-09-09 | 2005-10-19 | Angeletti P Ist Richerche Bio | Therapeutic compounds |
| US7399758B2 (en) * | 2005-09-12 | 2008-07-15 | Meanwell Nicholas A | Cyclopropyl fused indolobenzazepine HCV NS5B inhibitors |
| US7473688B2 (en) * | 2005-09-13 | 2009-01-06 | Bristol-Myers Squibb Company | Indolobenzazepine HCV NS5B inhibitors |
| US7456165B2 (en) * | 2006-02-08 | 2008-11-25 | Bristol-Myers Squibb Company | HCV NS5B inhibitors |
| GB0608928D0 (en) * | 2006-05-08 | 2006-06-14 | Angeletti P Ist Richerche Bio | Therapeutic agents |
-
2007
- 2007-05-03 US US11/743,921 patent/US7456166B2/en not_active Expired - Fee Related
- 2007-05-04 DE DE602007013036T patent/DE602007013036D1/de active Active
- 2007-05-04 EA EA200802346A patent/EA015286B1/ru not_active IP Right Cessation
- 2007-05-04 BR BRPI0711821-0A patent/BRPI0711821A2/pt not_active IP Right Cessation
- 2007-05-04 JP JP2009511151A patent/JP5284952B2/ja active Active
- 2007-05-04 MX MX2008014435A patent/MX2008014435A/es active IP Right Grant
- 2007-05-04 PL PL07761873T patent/PL2024375T3/pl unknown
- 2007-05-04 KR KR1020087027866A patent/KR101417145B1/ko active IP Right Grant
- 2007-05-04 DK DK07761873.4T patent/DK2024375T3/da active
- 2007-05-04 WO PCT/US2007/068209 patent/WO2007136982A1/en active Application Filing
- 2007-05-04 CA CA2651690A patent/CA2651690C/en not_active Expired - Fee Related
- 2007-05-04 AT AT07761873T patent/ATE501156T1/de active
- 2007-05-04 AU AU2007253998A patent/AU2007253998B2/en not_active Ceased
- 2007-05-04 EP EP07761873A patent/EP2024375B1/en active Active
- 2007-05-04 NZ NZ572555A patent/NZ572555A/en unknown
- 2007-05-04 SI SI200730612T patent/SI2024375T1/sl unknown
- 2007-05-15 PE PE2007000585A patent/PE20080070A1/es active IP Right Grant
- 2007-05-17 AR ARP070102138A patent/AR061008A1/es active IP Right Grant
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2008
- 2008-10-30 IL IL195025A patent/IL195025A/en not_active IP Right Cessation
- 2008-11-04 NO NO20084637A patent/NO341663B1/no not_active IP Right Cessation
- 2008-11-07 ZA ZA2008/09548A patent/ZA200809548B/en unknown
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2009
- 2009-03-31 HK HK09103021.8A patent/HK1122814A1/xx not_active IP Right Cessation
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2011
- 2011-03-16 HR HR20110194T patent/HRP20110194T1/hr unknown
- 2011-06-03 CY CY20111100539T patent/CY1111526T1/el unknown
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