HRP20100553T1 - Inhibitori replikacije virusa humane imunodeficijencije - Google Patents
Inhibitori replikacije virusa humane imunodeficijencije Download PDFInfo
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- HRP20100553T1 HRP20100553T1 HR20100553T HRP20100553T HRP20100553T1 HR P20100553 T1 HRP20100553 T1 HR P20100553T1 HR 20100553 T HR20100553 T HR 20100553T HR P20100553 T HRP20100553 T HR P20100553T HR P20100553 T1 HRP20100553 T1 HR P20100553T1
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- 241000725303 Human immunodeficiency virus Species 0.000 title 1
- 239000003112 inhibitor Substances 0.000 title 1
- 230000029812 viral genome replication Effects 0.000 title 1
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims abstract 34
- 125000000217 alkyl group Chemical group 0.000 claims abstract 18
- 150000001875 compounds Chemical class 0.000 claims abstract 17
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims abstract 9
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 24
- 125000005843 halogen group Chemical group 0.000 claims 14
- 125000000753 cycloalkyl group Chemical group 0.000 claims 11
- 125000001424 substituent group Chemical group 0.000 claims 11
- 125000004093 cyano group Chemical group *C#N 0.000 claims 10
- 125000004043 oxo group Chemical group O=* 0.000 claims 10
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 9
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims 8
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 8
- 229910052760 oxygen Inorganic materials 0.000 claims 6
- 229910052717 sulfur Inorganic materials 0.000 claims 6
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims 5
- 125000006656 (C2-C4) alkenyl group Chemical group 0.000 claims 5
- 125000000304 alkynyl group Chemical group 0.000 claims 5
- 150000002148 esters Chemical class 0.000 claims 5
- 125000005842 heteroatom Chemical group 0.000 claims 5
- 229910052757 nitrogen Inorganic materials 0.000 claims 5
- 150000003839 salts Chemical class 0.000 claims 5
- 125000001118 alkylidene group Chemical group 0.000 claims 3
- 125000003118 aryl group Chemical group 0.000 claims 3
- 125000001624 naphthyl group Chemical group 0.000 claims 3
- 125000001188 haloalkyl group Chemical group 0.000 claims 2
- 208000015181 infectious disease Diseases 0.000 claims 2
- 239000000825 pharmaceutical preparation Substances 0.000 claims 2
- 229920006395 saturated elastomer Polymers 0.000 claims 2
- 125000002373 5 membered heterocyclic group Chemical group 0.000 claims 1
- 125000004070 6 membered heterocyclic group Chemical group 0.000 claims 1
- 125000003341 7 membered heterocyclic group Chemical group 0.000 claims 1
- 208000031886 HIV Infections Diseases 0.000 claims 1
- 208000037357 HIV infectious disease Diseases 0.000 claims 1
- 241000124008 Mammalia Species 0.000 claims 1
- 239000003443 antiviral agent Substances 0.000 claims 1
- 125000006615 aromatic heterocyclic group Chemical group 0.000 claims 1
- 239000003814 drug Substances 0.000 claims 1
- 229940079593 drug Drugs 0.000 claims 1
- 208000033519 human immunodeficiency virus infectious disease Diseases 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 125000004585 polycyclic heterocycle group Chemical group 0.000 claims 1
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- C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D215/20—Oxygen atoms
- C07D215/22—Oxygen atoms attached in position 2 or 4
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- A61K31/00—Medicinal preparations containing organic active ingredients
- 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
- A61K31/352—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 condensed with carbocyclic rings, e.g. methantheline
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- 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
- A61K31/435—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
- A61K31/47—Quinolines; Isoquinolines
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- A61P31/12—Antivirals
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- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/12—Antivirals
- A61P31/14—Antivirals for RNA viruses
- A61P31/18—Antivirals for RNA viruses for HIV
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- 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
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- C07D215/12—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D215/14—Radicals substituted by oxygen atoms
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- C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
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- C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
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- C07D311/04—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring
- C07D311/06—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 2
- C07D311/08—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 2 not hydrogenated in the hetero ring
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- C07D311/04—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring
- C07D311/06—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 2
- C07D311/08—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 2 not hydrogenated in the hetero ring
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- C07D311/04—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring
- C07D311/06—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 2
- C07D311/08—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 2 not hydrogenated in the hetero ring
- C07D311/14—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 2 not hydrogenated in the hetero ring substituted in position 6 and unsubstituted in position 7
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- C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
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- C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
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Abstract
Spoj, naznačen time, da je atropizomer, racemat, enantiomer, dijastereomer ili tautomer spoja prikazanog formulom (I): gdjeveza a je dvostruka veza i veza b je jednostruka veza iliveza a je jednostruka veza i veza b je dvostruka veza; X je O ili NR1 kad je veza a jednostuka veza; ili X je N kad je veza a dvostuka veza; R1 je H, (C1-6)alkil, (C1-6)haloalkil, (C3-7)cikloalkil-(C1-6)alkil-, aril-(C1-6)alkil- ili Het-(C1-6)alkil-; gdje je svaki od (C1-6)alkil, (C3-7)cikloalkil-(C1-6)alkil-, aril-(C1-6)alkil- i Het-(C1-6)alkil- po želji supstituiran s -OH, -O(C1-6)alkil,
Claims (15)
1. Spoj, naznačen time, da je atropizomer, racemat, enantiomer, dijastereomer ili tautomer spoja prikazanog formulom (I):
[image]
gdje
veza a je dvostruka veza i veza b je jednostruka veza ili
veza a je jednostruka veza i veza b je dvostruka veza;
X je O ili NR1 kad je veza a jednostuka veza;
ili X je N kad je veza a dvostuka veza;
R1 je H, (C1-6)alkil, (C1-6)haloalkil, (C3-7)cikloalkil-(C1-6)alkil-, aril-(C1-6)alkil- ili Het-(C1-6)alkil-; gdje je svaki od (C1-6)alkil, (C3-7)cikloalkil-(C1-6)alkil-, aril-(C1-6)alkil- i Het-(C1-6)alkil- po želji supstituiran s -OH, -O(C1-6)alkil, -SH, -S(C1-6)alkil, -NH2, -NH(C1-6)alkil ili –N((C1-6)alkil)2;
R2 je H, (C1-6)alkil ili -O(C1-6)alkil kada veza b je jednostruka veza; ili R2 je O kada veza b je dvostruka veza;
R3 je (C1-6)alkil, (C1-6)haloalkil, (C2-6)alkenil, (C2-6)alkinil, (C3-7)cikloalkil-(C1-6)alkil-, aril-(C1-6)alkil-, Het-(C1-6)alkil- ili –Y-R31, i veza c je jednostruka veza; ili
R3 je (C1-6)alkiliden i veza c je dvostruka veza;
gdje Y je O ili S i R31 je (C1-6)alkil, (C1-6)haloalkil, (C2-6)alkenil, (C2-6)alkinil, (C3-7)cikloalkil, aril, (C3-7)cikloalkil-(C1-6)alkil-, aril-(C1-6)alkil- ili Het-(C1-6)alkil-;
gdje je svaki (C1-6)alkiliden, (C1-6)alkil, (C1-6)haloalkil, (C2-6)alkenil, (C2-6)alkinil, (C3-7)cikloalkil-(C1-6)alkil-, aril-(C1-6)alkil-, Het-(C1-6)alkil- i -Y-R31 po želji supstituiran s 1 do 3 supstituenada svaki nezavisno izabran iz skupine koju čine (C1-6)alkil, halo, cijano, okso ili -O(C1-6)alkil;
R4 je aril ili Het, gdje je svaki od aril i Het po želji supstituiran s 1 do 5 supstituenada od kojih je svaki nezavisno izabran iz skupine koju čine halo, (C1-6)alkil, (C2-6)alkenil, (C1-6)haloalkil, (C3-7)cikloalkil, -OH, -O(C1-6)alkil, -SH, -S(C1-6)alkil, -NH2, -NH(C1-6)alkil i –N((C1-6)alkil)2; gdje je (C1-6)alkil po želji supstituiran s hidroksi, cijano ili okso;
R6 i R7 je svaki nezavisno izabran iz skupine koju čine H, halo, (C1-6)alkil i (C1-6)haloalkil;
uz uvjet da kada
veza a je jednostruka veza i veza b je dvostruka veza; te
X je NR1; R1 je H; te R2 je O; te
R4 je nesupstituirani fenil; R6 je Cl; R7 je H; te
veza c je dvostruka veza; tada
R3 nije =CH-CH(CH3)2; te
gdje Het je 4- do 7-člani zasićeni, nezasićeni ili aromatski heterociklički prsten koji ima 1 do 4 heteroatoma od kojih je svaki neovisno izabran između O, N i S, ili 7- do 14-člani zasićeni, nezasićeni ili aromatski heteropoliciklički prsten koji ima gdje god je to moguće 1 do 5 heteroatoma od kojih je svaki neovisno izabran između O, N i S;
ili njegova sol ili ester.
2. Spoj u skladu sa zahtjevom 1, naznačen time, da R4 je naftil ili fenil, gdje je fenil po želji supstituiran s 1 do 3 supstituenada od kojih je svaki nezavisno izabran iz skupine koju čine halo, (C1-4)alkil, (C2-4)alkenil, (C1-4)haloalkil, (C3-7)cikloalkil, -OH, -O(C1-4)alkil, -SH, -S(C1-4)alkil, -NH2, -NH(C1-4)alkil i –N((C1-4)alkil)2; gdje je (C1-4)alkil po želji supstituiran s hidroksi, cijano ili okso.
3. Spoj u skladu sa zahtjevom 1, naznačen time, da R4 je Het po želji supstituiran s 1 do 5 supstituenada od kojih je svaki nezavisno izabran iz skupine koju čine halo, (C1-6)alkil, (C2-6)alkenil, (C1-6)haloalkil, (C3-7)cikloalkil, -OH, -O(C1-6)alkil, -SH, -S(C1-6)alkil, -NH2, -NH(C1-6)alkil i –N((C1-6)alkil)2; gdje je (C1-6)alkil po želji supstituiran s hidroksi, cijano ili okso.
4. Spoj u skladu sa zahtjevom 1, naznačen time, da je formule (Ia):
[image]
gdje
X je O ili NR1;
R1 je H, (C1-6)alkil, (C3-7)cikloalkil-(C1-6)alkil- ili Het-(C1-6)alkil-; gdje Het je 4- do 7-člani heterociklički prsten koji ima 1 do 3 heteroatoma od kojih je svaki nezavisno izabran iz skupine koju čine N, O ili S;
te gdje je svaki od (C1-6)alkil, (C3-7)cikloalkil-(C1-6)alkil- i Het-(C1-6)alkil- po želji supstituiran s -OH, -O(C1-3)alkil, -NH2, -NH(C1-3)alkil ili –N((C1-3)alkil)2;
R2 je O;
R3 je (C1-6)alkil ili (C2-6)alkenil; te
veza c je jednostruka veza;
R4 je naftil ili fenil, gdje je fenil po želji supstituiran s 1 do 3 supstituenda od kojih je svaki nezavisno izabran iz skupine koju čine halo, (C1-4)alkil, (C2-4)alkenil, (C1-4)haloalkil, (C3-7)cikloalkil, -OH, -O(C1-4)alkil, -SH, -S(C1-4)alkil, -NH2, -NH(C1-4)alkil i –N((C1-4)alkil)2; gdje je (C1-4)alkil po želji supstituiran s hidroksi, cijano ili okso;
R6 je H, halo, (C1-3)alkil ili (C1-3)haloalkil;
R7 je H ili F;
ili njegova sol ili ester.
5. Spoj u skladu sa zahtjevom 4, naznačen time, da R4 je fenil po želji supstituiran s 1 do 3 supstituenada od kojih je svaki nezavisno izabran iz skupine koju čine halo, (C1-4)alkil, (C2-4)alkenil, (C1-4)haloalkil, (C3-7)cikloalkil, -OH, -O(C1-4)alkil, -SH, -S(C1-4)alkil, -NH2, -NH(C1-4)alkil i –N((C1-4)alkil)2; gdje je (C1-4)alkil po želji supstituiran s hidroksi, cijano ili okso.
6. Spoj u skladu s jednim ili više zahtjeva od 1 do 5, naznačen time, da R6 je H, Cl, Br i R7 je H.
7. Spoj u skladu sa zahtjevom 1, naznačen time, da je formule (Id):
[image]
gdje
R2 je (C1-6)alkil ili -O(C1-6)alkil;
R3 je (C1-6)alkil, (C2-6)alkenil, -O-(C1-6)alkil, -O-(C1-6)haloalkil, -O-(C2-6)alkenil, -O-(C2-6)alkinil, -O-(C3-7)cikloalkil, -O-aril, (C3-7)cikloalkil-(C1-6)alkil-O-, aril-(C1-6)alkil-O- ili Het-(C1-6)alkil-O-;
gdje je svaki od -O-(C1-6)alkil, -O-(C2-6)alkenil, -O-(C2-6)alkinil, -O-(C3-7)cikloalkil, -O-aril, (C3-7)cikloalkil-(C1-6)alkil-O-, aril-(C1-6)alkil-O- ili Het-(C1-6)alkil-O- je po želji supstituiran s 1 do 3 supstituenada od kojih je svaki nezavisno izabran iz skupine koju čine (C1-6)alkil, halo, cijano, okso i -O(C1-6)alkil; te
veza c je jednostruka veza; ili
R3 je (C1-6)alkiliden i veza c je dvostruka veza;
R4 je naftil ili fenil, gdje je fenil po želji supstituiran s 1 do 3 supstituenada od kojih je svaki nezavisno izabran iz skupine koju čine halo, (C1-4)alkil, (C2-4)alkenil, (C1-4)haloalkil, (C3-7)cikloalkil, -OH, -O(C1-4)alkil, -SH, -S(C1-4)alkil, -NH2, -NH(C1-4)alkil i –N((C1-4)alkil)2; gdje je (C1-4)alkil po želji supstituiran s hidroksi, cijano ili okso; ili
R4 je Het po želji supstituiran s 1 do 5 supstituenada od kojih je svaki nezavisno izabran iz skupine koju čine halo, (C1-6)alkil, (C2-6)alkenil, (C1-6)haloalkil, (C3-7)cikloalkil, -OH, -O(C1-6)alkil, -SH, -S(C1-6)alkil, -NH2, -NH(C1-6)alkil i –N((C1-6)alkil)2; gdje je (C1-6)alkil po želji supstituiran s hidroksi, cijano ili okso;
R6 je H, halo, (C1-3)alkil ili (C1-3)haloalkil; te
R7 je H ili F;
ili njegova sol ili ester.
8. Spoj u skladu sa zahtjevom 7, naznačen time, da R4 je fenil po želji supstituiran s 1 do 3 supstituenada od koji je svaki nezavisno izabran iz skupine koju čine halo, (C1-4)alkil, (C2-4)alkenil, (C1-4)haloalkil, (C3-7)cikloalkil, -OH, -O(C1-4)alkil, -SH, -S(C1-4)alkil, -NH2, -NH(C1-4)alkil i –N((C1-4)alkil)2; gdje je (C1-4)alkil po želji supstituiran s hidroksi, cijano ili okso.
9. Spoj u skladu sa zahtjevom 7, naznačen time, da R4 je Het po želji supstituiran s 1 do 3 supstituenada od koji je svaki nezavisno izabran iz skupine koju čine halo, (C1-6)alkil ili -O(C1-6)alkil;
gdje Het je 5- ili 6-člani heterociklički prsten koji ima 1 do 3 heteroatoma od kojih je svaki nezavisno izabran iz skupine koju čine N, O ili S; ili Het je 9- ili 10-člani heteropoliciklički prsten koji ima 1 do 3 heteroatoma od kojih je svaki nezavisno izabran iz skupine koju čine N, O i S.
10. Spoj u skladu sa zahtjevom 1, naznačen time, da je formule:
[image]
gdje su R2, R3, R4, R6 i R7 definirani u skladu sa slijedećom tablicom:
[image]
[image]
[image]
[image]
[image]
[image]
[image]
[image]
[image]
[image]
[image]
[image]
[image]
[image]
[image]
[image]
[image]
[image]
[image]
[image]
11. Spoj u skladu sa zahtjevom 1, naznačen time, da je formule:
[image]
gdje su R1, R3, R4 i R6 definirani u skladu sa slijedećom tablicom:
[image]
[image]
12. Spoj u skladu sa zahtjevom 1, naznačen time, da je formule:
[image]
gdje su R3, R4 i R6 definirani u skladu sa slijedećom tablicom:
[image]
13. Farmaceutski pripravak, naznačen time, da sadrži terapeutski učinkovitu količinu spoja formule (I) kako je određeno u zahtjevu 1 ili njegovu farmaceutski prihvatljivu sol ili ester; te jednu ili više farmaceutski prihvatljivih podloga.
14. Farmaceutski pripravak kako je određen u zahtjevu 13, naznačen time, da dodatno sadrži najmanje još jedno drugačije antivirusno sredstvo.
15. Uporaba spoja formule (I) kako je određeno u zahtjevu 1, ili njegove farmaceutski prihvatljive soli ili estera, naznačena time, da se koristi u proizvodnji lijeka za liječenje HIV infekcije kod sisavca koji ima infekciju ili ima rizik od dobivanja infekcije.
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| US74731106P | 2006-05-16 | 2006-05-16 | |
| PCT/CA2007/000845 WO2007131350A1 (en) | 2006-05-16 | 2007-05-14 | Inhibitors of human immunodeficiency virus replication |
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| HRP20100553T1 true HRP20100553T1 (hr) | 2010-11-30 |
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| HR20100553T HRP20100553T1 (hr) | 2006-05-16 | 2010-10-12 | Inhibitori replikacije virusa humane imunodeficijencije |
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| EP (1) | EP2019825B9 (hr) |
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| AU (1) | AU2007250427B2 (hr) |
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| DE (1) | DE602007008874D1 (hr) |
| DK (1) | DK2019825T3 (hr) |
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| PE (1) | PE20080093A1 (hr) |
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2010
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