HRP20190808T1 - Spiro-indolini za liječenje i profilaksu infekcije respiratornim sincicijskim virusom (rsv) - Google Patents
Spiro-indolini za liječenje i profilaksu infekcije respiratornim sincicijskim virusom (rsv) Download PDFInfo
- Publication number
- HRP20190808T1 HRP20190808T1 HRP20190808TT HRP20190808T HRP20190808T1 HR P20190808 T1 HRP20190808 T1 HR P20190808T1 HR P20190808T T HRP20190808T T HR P20190808TT HR P20190808 T HRP20190808 T HR P20190808T HR P20190808 T1 HRP20190808 T1 HR P20190808T1
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- Prior art keywords
- compound
- membered
- substituted
- unsubstituted
- atom
- Prior art date
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- 238000011282 treatment Methods 0.000 title claims 4
- 206010061603 Respiratory syncytial virus infection Diseases 0.000 title claims 3
- 238000011321 prophylaxis Methods 0.000 title 1
- 208000030925 respiratory syncytial virus infectious disease Diseases 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims 18
- 125000000217 alkyl group Chemical group 0.000 claims 5
- 125000002947 alkylene group Chemical group 0.000 claims 3
- 125000000753 cycloalkyl group Chemical group 0.000 claims 3
- 239000003814 drug Substances 0.000 claims 3
- 125000000623 heterocyclic group Chemical group 0.000 claims 3
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 3
- 229940124597 therapeutic agent Drugs 0.000 claims 3
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims 2
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims 2
- 125000003342 alkenyl group Chemical class 0.000 claims 2
- 125000004432 carbon atom Chemical group C* 0.000 claims 2
- 239000003937 drug carrier Substances 0.000 claims 2
- 125000001153 fluoro group Chemical group F* 0.000 claims 2
- 125000005843 halogen group Chemical group 0.000 claims 2
- 125000001072 heteroaryl group Chemical group 0.000 claims 2
- 229910052739 hydrogen Inorganic materials 0.000 claims 2
- 239000001257 hydrogen Substances 0.000 claims 2
- 239000008194 pharmaceutical composition Substances 0.000 claims 2
- 229940121649 protein inhibitor Drugs 0.000 claims 2
- 239000012268 protein inhibitor Substances 0.000 claims 2
- 150000003839 salts Chemical class 0.000 claims 2
- 239000002904 solvent Substances 0.000 claims 2
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 1
- HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 claims 1
- 108010068327 4-hydroxyphenylpyruvate dioxygenase Proteins 0.000 claims 1
- 241000709661 Enterovirus Species 0.000 claims 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- 241001465754 Metazoa Species 0.000 claims 1
- 102000007982 Phosphoproteins Human genes 0.000 claims 1
- 108010089430 Phosphoproteins Proteins 0.000 claims 1
- 125000000304 alkynyl group Chemical class 0.000 claims 1
- 230000003110 anti-inflammatory effect Effects 0.000 claims 1
- 230000000840 anti-viral effect Effects 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
- 229910052731 fluorine Inorganic materials 0.000 claims 1
- 150000002431 hydrogen Chemical class 0.000 claims 1
- 125000003037 imidazol-2-yl group Chemical group [H]N1C([*])=NC([H])=C1[H] 0.000 claims 1
- 230000002519 immonomodulatory effect Effects 0.000 claims 1
- 206010022000 influenza Diseases 0.000 claims 1
- 230000002265 prevention Effects 0.000 claims 1
- 108090000623 proteins and genes Proteins 0.000 claims 1
- 102000004169 proteins and genes Human genes 0.000 claims 1
- 230000000241 respiratory effect Effects 0.000 claims 1
- 150000003527 tetrahydropyrans Chemical class 0.000 claims 1
- 238000002560 therapeutic procedure Methods 0.000 claims 1
- 241000712461 unidentified influenza virus Species 0.000 claims 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—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
- C07D401/02—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
- C07D401/06—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 carbon chain containing only aliphatic carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—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
- 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
- C07D471/04—Ortho-condensed systems
-
- 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
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
- A61K31/415—1,2-Diazoles
- A61K31/416—1,2-Diazoles condensed with carbocyclic ring systems, e.g. indazole
-
- 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
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
- A61K31/4164—1,3-Diazoles
- A61K31/4184—1,3-Diazoles condensed with carbocyclic rings, e.g. benzimidazoles
-
- 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
- A61K31/435—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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K45/00—Medicinal preparations containing active ingredients not provided for in groups A61K31/00 - A61K41/00
- A61K45/06—Mixtures of active ingredients without chemical characterisation, e.g. antiphlogistics and cardiaca
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
-
- 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
- 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
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- 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
- C07D403/06—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 linked by a carbon chain containing only aliphatic carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/14—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—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
- 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
- C07D471/10—Spiro-condensed systems
Claims (15)
1. Spoj koji je benzimidazol formule (I):
naznačen time, što:
- jedan od X i Y je N atom ili supstituirani C atom, a drugi je CH;
- L je jednostruka veza ili C1-3 alkilen;
- R1 je C1-6 alkil, C2-6 alkenil, C2-6 alkinil, 3-člani do 10-člani cikloalkil, 5-člani do 10-člani heterociklil ili 5-člani do 12-člani heteroaril, a svaki je nesupstituiran ili supstituiran;
- Z je -N(R2)2;
- svaki R2 je zasebno vodik, C1-6 alkil, C2-6 alkenil ili C2-6 alkinil, pri čemu su spomenute alkenilne i alkinilne grupe nesupstituirane ili supstituirane; i
- m je 1;
ili njegova farmaceutski prihvatljiva sol.
2. Spoj prema patentnom zahtjevu 1, naznačen time, što je jedan od X i Y N atom ili C atom supstituiran atomom halogena, a drugi je CH.
3. Spoj prema patentnom zahtjevu 1, naznačen time, što je L jednostruka veza ili C1 alkilen.
4. Spoj prema bilo kojem od prethodnih patentnih zahtjeva, naznačen time, što je R1 C3-6 alkil, C3-6 alkenil, 5-člani ili 6-člani cikloalkil, 5-člani ili 6-člani heterociklil ili 5-člani ili 6-člani heteroaril, a svaki je nesupstituiran ili supstituiran.
5. Spoj prema patentnom zahtjevu 4, naznačen time, što je R1 C5-6 alkil koji je nesupstituiran ili supstituiran s jednim, dva, tri ili četiri atoma halogena, R1 je 6-člani cikloalkil supstituiran s jednom, dvije, tri ili četiri -OH grupe ili R1 je nesupstituirani 6-člani heterociklil.
6. Spoj prema patentnom zahtjevu 1, naznačen time, što je Z NH2.
7. Spoj prema bilo kojem od prethodnih zahtjeva, naznačen time, što je svaki R2 zasebno vodik ili C1-4 alkil.
8. Spoj prema patentnom zahtjevu 1, naznačen time, što u formuli (I):
- jedan od X i Y je N atom ili C supstituiran atomom fluora, a drugi je CH;
- R1 je C5-6 alkil, koji je nesupstituiran ili supstituiran s jednim, dva, tri ili četiri atoma fluora, R1 je cikloheksil koji je nesupstituiran ili supstituiran s jednom ili dvije -OH grupe ili R1 je nesupstituirani tetrahidropiran;
- m je 1
- L je jednostruka veza ili C1 alkilen; i
- Z je NH2.
9. Spoj prema patentnom zahtjevu 1 koji je odabran iz:
- 1’-{[5-(aminometil)-1-(4,4,4-trifluorobutil)-1H-1,3-benzodiazol-2-il]metil}-6’-fluoro-1’,2’-dihidrospiro[ciklopropan-1,3’-indol]-2’-ona;
- 1’-((5-(aminometil)-1-(4,4,4-trifluorobutil)-1H-benzo[d]imidazol-2-il)metil)spiro[ciklopropan-1,3’-pirolo[2,3-b]piridin]-2’(1’H)-ona;
- 1’-((5-(aminometil)-1-izopentil-1H-benzo[d]imidazol-2-il)metil)spiro[ciklopropan-1,3’-pirolo[2,3-b]piridin]-2’(1’H)-ona;
- 1’-((5-(aminometil)-1-izopentil-1H-benzo[d]imidazol-2-il)metil)spiro[ciklopropan-1,3’-pirolo[2,3-c]piridin]-2’(1’H)-ona; i
- 1’-((5-(aminometil)-1-(tetrahidro-2H-piran-4-yl)-1H-benzo[d]imidazol-2-il)metil)-6’-fluorospiro[ciklopropan-1,3’-indolin]-2’-ona;
- 1’-((5-(aminometil)-1-((1R,4R)-4-hidroksicikloheksil)-1H-benzo[d]imidazol-2-il)metil)-6’-fluorospiro[ciklopropan-1,3’-indolin]-2’-ona
i njihovih farmaceutski prihvatljivih soli.
10. Farmaceutski pripravak koji sadrži spoj kako je definirano prema bilo kojem patentnom zahtjevu od 1 do 9 i farmaceutski prihvatljivi nosač ili otapalo.
11. Spoj kako je definirano prema bilo kojem patentnom zahtjevu od 1 do 9, za primjenu u liječenju čovjeka ili životinje pomoću terapije.
12. Spoj kako je definirano prema bilo kojem patentnom zahtjevu od 1 do 9 za primjenu u liječenju ili sprječavanju infekcije RSV-om.
13. Proizvod koji sadrži:
(a) spoj kako je definirano prema bilo kojem patentnom zahtjevu od 1 do 9; i
(b) jedno ili više dodatnih terapijskih sredstava;
za istovremenu, odvojenu ili sekvencijalnu primjenu u liječenju subjekta koji pati od ili je podložan infekciji RSV-om.
14. Proizvod za primjenu prema patentnom zahtjevu 13, naznačen time, što je dodatno terapijsko sredstvo:
(i) inhibitor proteina nukleokapsida(N) RSV-a;
(ii) drugi inhibitor proteina, primjerice neki koji inhibira fosfoprotein (P) i/ili veliki (L) protein;
(iii) anti-RSV monoklonalno antitijelo, kao što je antitijelo na F-protein;
(iv) spoj imunomodulirajućeg toličnog receptora;
(v) drugi resipratorni, protuvirusni spoj, kao što je spoj protiv gripe i/ili rinovirusa; i/ili
(vi) protuupalni spoj.
15. Farmaceutski pripravak koji sadrži (a) spoj kako je definirano prema bilo kojem patentnom zahtjevu od 1 do 9 i (b) jedno ili više dodatnih terapijskih sredstava, kako je definirano u patentnom zahtjevu 14, zajedno s farmaceutski prihvatljivim nosačem ili otapalom.
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GBGB1417707.5A GB201417707D0 (en) | 2014-10-07 | 2014-10-07 | Pharmaceutical compounds |
PCT/GB2015/052920 WO2016055780A1 (en) | 2014-10-07 | 2015-10-06 | Spiro-indolines for the treatment and prophylaxis of respiratory syncytial virus infection (rsv) |
EP15782033.3A EP3204375B1 (en) | 2014-10-07 | 2015-10-06 | Spiro-indolines for the treatment and prophylaxis of respiratory syncytial virus infection (rsv) |
Publications (1)
Publication Number | Publication Date |
---|---|
HRP20190808T1 true HRP20190808T1 (hr) | 2019-08-23 |
Family
ID=51946966
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
HRP20190808TT HRP20190808T1 (hr) | 2014-10-07 | 2019-04-30 | Spiro-indolini za liječenje i profilaksu infekcije respiratornim sincicijskim virusom (rsv) |
Country Status (30)
Country | Link |
---|---|
US (1) | US10106539B2 (hr) |
EP (1) | EP3204375B1 (hr) |
JP (1) | JP6695334B2 (hr) |
KR (2) | KR102561796B1 (hr) |
CN (1) | CN107108557B (hr) |
AR (1) | AR102181A1 (hr) |
AU (1) | AU2015329778B2 (hr) |
BR (1) | BR112017007311B1 (hr) |
CA (1) | CA2963740C (hr) |
CL (1) | CL2017000839A1 (hr) |
CO (1) | CO2017004603A2 (hr) |
CY (1) | CY1121564T1 (hr) |
DK (1) | DK3204375T3 (hr) |
ES (1) | ES2718976T3 (hr) |
GB (1) | GB201417707D0 (hr) |
HR (1) | HRP20190808T1 (hr) |
HU (1) | HUE043553T2 (hr) |
LT (1) | LT3204375T (hr) |
MX (1) | MX2017004425A (hr) |
NZ (1) | NZ731323A (hr) |
PE (1) | PE20170949A1 (hr) |
PL (1) | PL3204375T3 (hr) |
PT (1) | PT3204375T (hr) |
RS (1) | RS58706B1 (hr) |
RU (1) | RU2734248C2 (hr) |
SG (1) | SG11201702766YA (hr) |
SI (1) | SI3204375T1 (hr) |
TR (1) | TR201903362T4 (hr) |
TW (1) | TWI718107B (hr) |
WO (1) | WO2016055780A1 (hr) |
Families Citing this family (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP3305790B1 (en) | 2015-06-08 | 2020-08-05 | Shangdong Danhong Pharmaceutical Co., Ltd. | Method for preparing imidazole derivative and intermediate thereof and crystal form |
JP6944514B2 (ja) | 2016-08-04 | 2021-10-06 | アールイーヴァイラル リミテッド | ピリミジン誘導体および呼吸器合胞体ウイルス感染の治療または予防におけるそれらの使用 |
GB201711704D0 (en) * | 2017-07-20 | 2017-09-06 | Reviral Ltd | Pharmaceutical compounds |
GB201721812D0 (en) * | 2017-12-22 | 2018-02-07 | Reviral Ltd | Pharmaceutical compounds |
CN116077494A (zh) * | 2023-01-11 | 2023-05-09 | 黑龙江中医药大学 | 一种治疗呼吸道合胞病毒的药物组合物及其制备方法 |
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KR20160007629A (ko) * | 2013-05-14 | 2016-01-20 | 에프. 호프만-라 로슈 아게 | 호흡기 세포융합 바이러스 감염의 치료 및 예방을 위한 아자-옥소-인돌 |
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BR112016002638A2 (pt) * | 2013-08-12 | 2017-08-01 | Hoffmann La Roche | novos aza-oxo-indóis para o tratamento e profilaxia de infecção pelo virus sincicial respiratório |
EP3033333A1 (en) * | 2013-08-15 | 2016-06-22 | F. Hoffmann-La Roche AG | Novel aza-oxo-indoles for the treatment and prophylaxis of respiratory syncytial virus infection |
CN105431419A (zh) * | 2013-08-15 | 2016-03-23 | 豪夫迈·罗氏有限公司 | 新的用于治疗和预防呼吸道合胞病毒感染的氮杂-氧代-吲哚 |
KR20160030569A (ko) * | 2013-08-15 | 2016-03-18 | 에프. 호프만-라 로슈 아게 | 호흡기 세포융합 바이러스 감염의 치료 및 예방을 위한 신규한 아자-옥소-인돌 |
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