HRP20192275T1 - Novi spojevi 3,4-dihidro-2h-izokinolin-1-ona i 2,3-dihidro-izoindol-1-ona - Google Patents
Novi spojevi 3,4-dihidro-2h-izokinolin-1-ona i 2,3-dihidro-izoindol-1-ona Download PDFInfo
- Publication number
- HRP20192275T1 HRP20192275T1 HRP20192275TT HRP20192275T HRP20192275T1 HR P20192275 T1 HRP20192275 T1 HR P20192275T1 HR P20192275T T HRP20192275T T HR P20192275TT HR P20192275 T HRP20192275 T HR P20192275T HR P20192275 T1 HRP20192275 T1 HR P20192275T1
- Authority
- HR
- Croatia
- Prior art keywords
- chloro
- amino
- pyridin
- isoindol
- dimethyl
- Prior art date
Links
- PXZQEOJJUGGUIB-UHFFFAOYSA-N isoindolin-1-one Chemical class C1=CC=C2C(=O)NCC2=C1 PXZQEOJJUGGUIB-UHFFFAOYSA-N 0.000 title claims 3
- YWPMKTWUFVOFPL-UHFFFAOYSA-N 3,4-dihydro-2h-isoquinolin-1-one Chemical compound C1=CC=C2C(=O)NCCC2=C1 YWPMKTWUFVOFPL-UHFFFAOYSA-N 0.000 title 1
- XTBAPWCYTNCZTO-UHFFFAOYSA-N isoindol-1-one Chemical compound C1=CC=C2C(=O)N=CC2=C1 XTBAPWCYTNCZTO-UHFFFAOYSA-N 0.000 claims 24
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 19
- 150000001875 compounds Chemical class 0.000 claims 18
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims 17
- -1 1-acetylazetidin-3-yl Chemical group 0.000 claims 6
- 150000003839 salts Chemical class 0.000 claims 5
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 4
- 125000000217 alkyl group Chemical group 0.000 claims 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 3
- RLEDJJSZJVZPFT-UHFFFAOYSA-N 5-chloro-2-[5-[(1-ethylsulfonylazetidin-3-yl)amino]pyridin-3-yl]-3,3-dimethylisoindol-1-one Chemical compound C1N(S(=O)(=O)CC)CC1NC1=CN=CC(N2C(C3=CC(Cl)=CC=C3C2=O)(C)C)=C1 RLEDJJSZJVZPFT-UHFFFAOYSA-N 0.000 claims 2
- UFAHHYBOWAFUQY-UHFFFAOYSA-N 5-chloro-2-[5-[(1-ethylsulfonylpiperidin-4-yl)amino]pyridin-3-yl]-3,3-dimethylisoindol-1-one Chemical compound C1CN(S(=O)(=O)CC)CCC1NC1=CN=CC(N2C(C3=CC(Cl)=CC=C3C2=O)(C)C)=C1 UFAHHYBOWAFUQY-UHFFFAOYSA-N 0.000 claims 2
- WUUPUGQPOHAPTH-UHFFFAOYSA-N 5-chloro-3,3-dimethyl-2-[5-[(1-propanoylazetidin-3-yl)amino]pyridin-3-yl]isoindol-1-one Chemical compound C1N(C(=O)CC)CC1NC1=CN=CC(N2C(C3=CC(Cl)=CC=C3C2=O)(C)C)=C1 WUUPUGQPOHAPTH-UHFFFAOYSA-N 0.000 claims 2
- 125000001309 chloro group Chemical group Cl* 0.000 claims 2
- 229910052736 halogen Inorganic materials 0.000 claims 2
- 150000002367 halogens Chemical class 0.000 claims 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims 2
- SEUIJWDSZHSZGF-UHFFFAOYSA-N 2-[5-[(1-acetylazetidin-3-yl)-methylamino]pyridin-3-yl]-5-chloro-3,3-dimethylisoindol-1-one Chemical compound C=1N=CC(N2C(C3=CC(Cl)=CC=C3C2=O)(C)C)=CC=1N(C)C1CN(C(C)=O)C1 SEUIJWDSZHSZGF-UHFFFAOYSA-N 0.000 claims 1
- PJIDTARQNMHGHA-UHFFFAOYSA-N 2-[5-[(1-acetylazetidin-3-yl)amino]pyridin-3-yl]-6-chloro-3,4-dihydroisoquinolin-1-one Chemical compound C1N(C(=O)C)CC1NC1=CN=CC(N2C(C3=CC=C(Cl)C=C3CC2)=O)=C1 PJIDTARQNMHGHA-UHFFFAOYSA-N 0.000 claims 1
- NRWCXYWJOLOOMM-UHFFFAOYSA-N 2-[5-[(1-acetylpiperidin-4-yl)amino]pyridin-3-yl]-5-chloro-3,3-dimethylisoindol-1-one Chemical compound C1CN(C(=O)C)CCC1NC1=CN=CC(N2C(C3=CC(Cl)=CC=C3C2=O)(C)C)=C1 NRWCXYWJOLOOMM-UHFFFAOYSA-N 0.000 claims 1
- NQPKIMJXCYUNDZ-UHFFFAOYSA-N 2-[5-[(1-ethylsulfonylpiperidin-4-yl)amino]pyridin-3-yl]-3,3-dimethyl-1-oxoisoindole-5-carbonitrile Chemical compound C1CN(S(=O)(=O)CC)CCC1NC1=CN=CC(N2C(C3=CC(=CC=C3C2=O)C#N)(C)C)=C1 NQPKIMJXCYUNDZ-UHFFFAOYSA-N 0.000 claims 1
- WJSWPNQEJDWGQU-UHFFFAOYSA-N 2-[5-[(2-acetyl-2-azaspiro[3.3]heptan-6-yl)amino]pyridin-3-yl]-5-chloro-3,3-dimethylisoindol-1-one Chemical compound C1N(C(=O)C)CC11CC(NC=2C=C(C=NC=2)N2C(C3=CC(Cl)=CC=C3C2=O)(C)C)C1 WJSWPNQEJDWGQU-UHFFFAOYSA-N 0.000 claims 1
- JCIJGKORACXSDQ-UHFFFAOYSA-N 3,3-dimethyl-1-oxo-2-[5-[(1-propanoylazetidin-3-yl)amino]pyridin-3-yl]isoindole-5-carbonitrile Chemical compound C1N(C(=O)CC)CC1NC1=CN=CC(N2C(C3=CC(=CC=C3C2=O)C#N)(C)C)=C1 JCIJGKORACXSDQ-UHFFFAOYSA-N 0.000 claims 1
- XNKUQIVPMRJWTJ-UHFFFAOYSA-N 3,3-dimethyl-1-oxo-2-[5-[(1-propanoylpiperidin-4-yl)amino]pyridin-3-yl]isoindole-5-carbonitrile Chemical compound C1CN(C(=O)CC)CCC1NC1=CN=CC(N2C(C3=CC(=CC=C3C2=O)C#N)(C)C)=C1 XNKUQIVPMRJWTJ-UHFFFAOYSA-N 0.000 claims 1
- OZYMGUUSBHACNX-UHFFFAOYSA-N 5-chloro-2-[5-[(1-ethylsulfonylazetidin-3-yl)-methylamino]pyridin-3-yl]-3,3-dimethylisoindol-1-one Chemical compound C1N(S(=O)(=O)CC)CC1N(C)C1=CN=CC(N2C(C3=CC(Cl)=CC=C3C2=O)(C)C)=C1 OZYMGUUSBHACNX-UHFFFAOYSA-N 0.000 claims 1
- FDILLSVSLOUAEN-UHFFFAOYSA-N 5-chloro-2-[5-[(1-ethylsulfonylazetidin-3-yl)amino]pyridin-3-yl]-3-methyl-3h-isoindol-1-one Chemical compound C1N(S(=O)(=O)CC)CC1NC1=CN=CC(N2C(C3=CC=C(Cl)C=C3C2C)=O)=C1 FDILLSVSLOUAEN-UHFFFAOYSA-N 0.000 claims 1
- KYQZXRCQALDMNX-UHFFFAOYSA-N 5-chloro-2-[5-[(1-ethylsulfonylpiperidin-4-yl)-methylamino]pyridin-3-yl]-3,3-dimethylisoindol-1-one Chemical compound C1CN(S(=O)(=O)CC)CCC1N(C)C1=CN=CC(N2C(C3=CC(Cl)=CC=C3C2=O)(C)C)=C1 KYQZXRCQALDMNX-UHFFFAOYSA-N 0.000 claims 1
- YOICWQUHZUKZFB-UHFFFAOYSA-N 5-chloro-2-[5-[(1-propanoylazetidin-3-yl)amino]pyridin-3-yl]-3h-isoindol-1-one Chemical compound C1N(C(=O)CC)CC1NC1=CN=CC(N2C(C3=CC=C(Cl)C=C3C2)=O)=C1 YOICWQUHZUKZFB-UHFFFAOYSA-N 0.000 claims 1
- IDYGYIPQTCPCPE-UHFFFAOYSA-N 5-chloro-2-[5-[(2-ethylsulfonyl-2-azaspiro[3.3]heptan-6-yl)amino]pyridin-3-yl]-3,3-dimethylisoindol-1-one Chemical compound C1N(S(=O)(=O)CC)CC11CC(NC=2C=C(C=NC=2)N2C(C3=CC(Cl)=CC=C3C2=O)(C)C)C1 IDYGYIPQTCPCPE-UHFFFAOYSA-N 0.000 claims 1
- QGULZDHBGCOVBZ-UHFFFAOYSA-N 5-chloro-3,3-dimethyl-2-[5-[(1-methylsulfonylazetidin-3-yl)amino]pyridin-3-yl]isoindol-1-one Chemical compound CC1(C)N(C(=O)c2ccc(Cl)cc12)c1cncc(NC2CN(C2)S(C)(=O)=O)c1 QGULZDHBGCOVBZ-UHFFFAOYSA-N 0.000 claims 1
- LMBJLDSRCHCXGY-UHFFFAOYSA-N 5-chloro-3,3-dimethyl-2-[5-[(2-propan-2-ylsulfonyl-2-azaspiro[3.3]heptan-6-yl)amino]pyridin-3-yl]isoindol-1-one Chemical compound C1N(S(=O)(=O)C(C)C)CC11CC(NC=2C=C(C=NC=2)N2C(C3=CC(Cl)=CC=C3C2=O)(C)C)C1 LMBJLDSRCHCXGY-UHFFFAOYSA-N 0.000 claims 1
- SSTITLGLPNFUPE-UHFFFAOYSA-N 5-chloro-3,3-dimethyl-2-[5-[(2-propanoyl-2-azaspiro[3.3]heptan-6-yl)amino]pyridin-3-yl]isoindol-1-one Chemical compound C1N(C(=O)CC)CC11CC(NC=2C=C(C=NC=2)N2C(C3=CC(Cl)=CC=C3C2=O)(C)C)C1 SSTITLGLPNFUPE-UHFFFAOYSA-N 0.000 claims 1
- HUZFGXBGIOLUDH-UHFFFAOYSA-N 5-chloro-3,3-dimethyl-2-[5-[methyl-(1-methylsulfonylazetidin-3-yl)amino]pyridin-3-yl]isoindol-1-one Chemical compound C=1N=CC(N2C(C3=CC(Cl)=CC=C3C2=O)(C)C)=CC=1N(C)C1CN(S(C)(=O)=O)C1 HUZFGXBGIOLUDH-UHFFFAOYSA-N 0.000 claims 1
- BHAKQQSLQFBCIZ-UHFFFAOYSA-N 5-chloro-3,3-dimethyl-2-[5-[methyl-(1-methylsulfonylpiperidin-4-yl)amino]pyridin-3-yl]isoindol-1-one Chemical compound C=1N=CC(N2C(C3=CC(Cl)=CC=C3C2=O)(C)C)=CC=1N(C)C1CCN(S(C)(=O)=O)CC1 BHAKQQSLQFBCIZ-UHFFFAOYSA-N 0.000 claims 1
- MHEQFRKGPGSCFA-UHFFFAOYSA-N 5-chloro-3,3-dimethyl-2-[5-[methyl-(1-propanoylazetidin-3-yl)amino]pyridin-3-yl]isoindol-1-one Chemical compound C1N(C(=O)CC)CC1N(C)C1=CN=CC(N2C(C3=CC(Cl)=CC=C3C2=O)(C)C)=C1 MHEQFRKGPGSCFA-UHFFFAOYSA-N 0.000 claims 1
- YJHSVJKTJNJPMR-UHFFFAOYSA-N 5-chloro-3,3-dimethyl-2-[5-[methyl-(1-propanoylpiperidin-4-yl)amino]pyridin-3-yl]isoindol-1-one Chemical compound C1CN(C(=O)CC)CCC1N(C)C1=CN=CC(N2C(C3=CC(Cl)=CC=C3C2=O)(C)C)=C1 YJHSVJKTJNJPMR-UHFFFAOYSA-N 0.000 claims 1
- UTCGJJCCPVKGQX-UHFFFAOYSA-N 5-chloro-3,3-dimethyl-2-[5-[methyl-(1-propylsulfonylazetidin-3-yl)amino]pyridin-3-yl]isoindol-1-one Chemical compound C1N(S(=O)(=O)CCC)CC1N(C)C1=CN=CC(N2C(C3=CC(Cl)=CC=C3C2=O)(C)C)=C1 UTCGJJCCPVKGQX-UHFFFAOYSA-N 0.000 claims 1
- ZTWWIDHBLIYTCM-UHFFFAOYSA-N 5-chloro-3-methyl-2-[5-[(1-propanoylazetidin-3-yl)amino]pyridin-3-yl]-3h-isoindol-1-one Chemical compound C1N(C(=O)CC)CC1NC1=CN=CC(N2C(C3=CC=C(Cl)C=C3C2C)=O)=C1 ZTWWIDHBLIYTCM-UHFFFAOYSA-N 0.000 claims 1
- DYRUCUTXSCOCRR-UHFFFAOYSA-N 6-chloro-2-[5-[(1-ethylsulfonylazetidin-3-yl)amino]pyridin-3-yl]-3,4-dihydroisoquinolin-1-one Chemical compound C1N(S(=O)(=O)CC)CC1NC1=CN=CC(N2C(C3=CC=C(Cl)C=C3CC2)=O)=C1 DYRUCUTXSCOCRR-UHFFFAOYSA-N 0.000 claims 1
- ZMOGYSYYIXNXBS-UHFFFAOYSA-N 6-chloro-2-[5-[(1-propan-2-ylsulfonylazetidin-3-yl)amino]pyridin-3-yl]-3,4-dihydroisoquinolin-1-one Chemical compound C1N(S(=O)(=O)C(C)C)CC1NC1=CN=CC(N2C(C3=CC=C(Cl)C=C3CC2)=O)=C1 ZMOGYSYYIXNXBS-UHFFFAOYSA-N 0.000 claims 1
- JOEQXCXAZZQVGT-UHFFFAOYSA-N 6-chloro-2-[5-[(1-propanoylazetidin-3-yl)amino]pyridin-3-yl]-3,4-dihydroisoquinolin-1-one Chemical compound C1N(C(=O)CC)CC1NC1=CN=CC(N2C(C3=CC=C(Cl)C=C3CC2)=O)=C1 JOEQXCXAZZQVGT-UHFFFAOYSA-N 0.000 claims 1
- 206010007559 Cardiac failure congestive Diseases 0.000 claims 1
- 208000016998 Conn syndrome Diseases 0.000 claims 1
- 208000014311 Cushing syndrome Diseases 0.000 claims 1
- 206010019280 Heart failures Diseases 0.000 claims 1
- 206010020772 Hypertension Diseases 0.000 claims 1
- 239000013543 active substance Substances 0.000 claims 1
- 208000020832 chronic kidney disease Diseases 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 238000000034 method Methods 0.000 claims 1
- 239000000825 pharmaceutical preparation Substances 0.000 claims 1
- 208000013846 primary aldosteronism Diseases 0.000 claims 1
- 201000009395 primary hyperaldosteronism Diseases 0.000 claims 1
- 238000011321 prophylaxis Methods 0.000 claims 1
- 238000011282 treatment Methods 0.000 claims 1
- ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 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
- C07D401/14—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 three or more hetero rings
-
- 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
- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
- A61K31/4427—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P13/00—Drugs for disorders of the urinary system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P13/00—Drugs for disorders of the urinary system
- A61P13/12—Drugs for disorders of the urinary system of the kidneys
-
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P5/00—Drugs for disorders of the endocrine system
- A61P5/38—Drugs for disorders of the endocrine system of the suprarenal hormones
- A61P5/42—Drugs for disorders of the endocrine system of the suprarenal hormones for decreasing, blocking or antagonising the activity of mineralocorticosteroids
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P5/00—Drugs for disorders of the endocrine system
- A61P5/38—Drugs for disorders of the endocrine system of the suprarenal hormones
- A61P5/46—Drugs for disorders of the endocrine system of the suprarenal hormones for decreasing, blocking or antagonising the activity of glucocorticosteroids
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/04—Inotropic agents, i.e. stimulants of cardiac contraction; Drugs for heart failure
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/12—Antihypertensives
Claims (13)
1. Spojevi, naznačeni time, da su predstavljeni formulom (I)
u kojoj
su R1 i R2 alkil;
R7 i R9 su H;
R8 i R11 zajedno čine −CH2-CH2−;
R10 je H;
A je −S(O)2−;
R12 je alkil;
R13 je kloro;
R14 je H;
R15 je H;
m i n su nula;
p je 1;
i njihove farmaceutski prihvatljive soli.
2. Spoj prema patentnom zahtjevu 1, naznačen time, da
su R1 i R2 metil;
R7 i R9 su H;
R8 i R11 zajedno čine −CH2-CH2−;
R10 je H;
A je −S(O)2−;
R12 je etil;
R13 je kloro;
R14 je H ili alkil;
R15 je H;
m i n su nula;
p je 1;
i njegove farmaceutski prihvatljive soli.
3. Spoj prema bilo kojem od patentnih zahtjeva 1 do 2, naznačen time, da su R1 i R2 metil.
4. Spoj prema bilo kojem od patentnih zahtjeva 1 do 3, naznačen time, da je R12 metil, etil, propil ili izopropil.
5. Spoj prema bilo kojem od patentnih zahtjeva 1 do 4, naznačen time, da je R12 etil, propil ili izopropil.
6. Spoj prema bilo kojem od patentnih zahtjeva 1 do 5, naznačen time, da je R12 etil.
7. Spoj, naznačen time, da je odabran iz skupine koju čine
2-[5-[(1-acetilazetidin-3-il)amino]piridin-3-il]-5-kloro-3,3-dimetilzoindol-1-on;
2-[5-[(1-acetilazetidin-3-il)-metilamino]piridin-3-il]-5-kloro-3,3-dimetilizoindol-1-on;
5-kloro-2-[5-[[(3R ili 3S)-1-etilsulfonilpirolidin-3-il]-metilamino]piridin-3-il]-3,3-dimetilizoindol-1-on;
5-kloro-2-[5-[[(3S ili 3R)-1-etilsulfonilpirolidin-3-il]-metilamino]piridin-3-il]-3,3-dimetilizoindol-1-on;
2-[5-[(1-acetilpiperidin-4-il)amino]piridin-3-il]-5-kloro-3,3-dimetilizoindol-1-on;
5-kloro-2-[5-[(1-etilsulfonilpiperidin-4-il)amino]piridin-3-il]-3,3-dimetilizoindol-1-on;
5-kloro-2-[5-[(1-etilsulfonilazetidin-3-il)amino]piridin-3-il]-3,3-dimetilizoindol-1-on;
5-kloro-3,3-dimetil-2-[5-[(1-metilsulfonilazetidin-3-il)amino]piridin-3-il]izoindol-1-on;
5-kloro-3,3-dimetil-2-[5-[(1-propanoilazetidin-3-il)amino]piridin-3-il]izoindol-1-on;
5-kloro-2-[5-[(1-etilsulfonilazetidin-3-il)-metilamino]piridin-3-il]-3,3-dimetilizoindol-1-on;
5-kloro-3,3-dimetil-2-[5-[metil-(1-metilsulfonilazetidin-3-il)amino]piridin-3-il]izoindol-1-on;
5-kloro-3,3-dimetil-2-[5-[metil-(1-propanoilazetidin-3-il)amino]piridin-3-il]izoindol-1-on;
5-kloro-3,3-dimetil-2-[5-[metil-(1-propan-2-ilsulfoilazetidin-3-il)amino]piridin-3-il]izoindol-1-on;
5-kloro-3,3-dimetil-2-[5-[metil-(1-propilsulfonilazetidin-3-il)amino]piridin-3-il]izoindol-1-on;
5-kloro-3,3-dimetil-2-[5-[metil-[(3S ili 3R)-1-propan-2-ilsulfonilpirolidin-3-il]amino]piridin-3-il]izoindol-1-on;
5-kloro-3,3-dimetil-2-[5-[metil-[(3R ili 3S)-1-propan-2-ilsulfonilpirolidin-3-il]amino]piridin-3-il]izoindol-1-on;
5-kloro-3,3-dimetil-2-[5-[metil-[(3S ili 3R)-1-propilsulfonilpirolidin-3-il]amino]piridin-3-il]izoindol-1-on;
5-kloro-3,3-dimetil-2-[5-[metil-[(3R ili 3S)-1-propilsulfonilpirolidin-3-il]amino]piridin-3-il]izoindol-1-on;
5-kloro-3,3-dimetil-2-[5-[metil-(1-propanoilpiperidin-4-il)amino]piridin-3-il]izoindol-1-on;
5-kloro-2-[5-[(1-etilsulfonilpiperidin-4-il)-metilamino]piridin-3-il]-3,3-dimetilizoindol-1-on;
5-kloro-3,3-dimetil-2-[5-[metil-(1-metilsulfonilpiperidin-4-il)amino]piridin-3-il]izoindol-1-on;
5-kloro-3,3-dimetil-2-[5-[[(3R ili 3S)-1-metilsulfonilpiperidin-3-il]amino]piridin-3-il]izoindol-1-on;
5-kloro-3,3-dimetil-2-[5-[[(3S ili 3R)-1-metilsulfonilpiperidin-3-il]amino]piridin-3-il]izoindol-1-on;
5-kloro-2-[5-[[(3R ili 3S)-1-etilsulfonilpiperidin-3-il]amino]piridin-3-il]-3,3-dimetilizoindol-1-on;
5-kloro-2-[5-[[(3S ili 3R)-1-etilsulfonilpiperidin-3-il]amino]piridin-3-il]-3,3-dimetilizoindol-1-on;
5-kloro-3,3-dimetil-2-[5-[[(3R ili 3S)-1-propan-2-ilsulfonilpiperidin-3-il]amino]piridin-3-il]izoindol-1-on;
5-kloro-3,3-dimetil-2-[5-[[(3S ili 3R)-1-propan-2-ilsulfonilpiperidin-3-il]amino]piridin-3-il]izoindol-1-on;
5-kloro-2-[5-[(1-propanoilazetidin-3-il)amino]piridin-3-il]-3H-izoindol-1-on;
6-kloro-2-[5-[(1-propanoilazetidin-3-il)amino]piridin-3-il]-3,4-dihidroizokinolin-1-on;
6-kloro-2-[5-[(1-etilsulfonilazetidin-3-il)amino]piridin-3-il]-3,4-dihidroizokinolin-1-on;
6-kloro-2-[5-[(1-propan-2-ilsulfonilazetidin-3-il)amino]piridin-3-il]-3,4-dihidroizokinolin-1-on;
2-[5-[(1-acetilazetidin-3-il)amino]piridin-3-il]-6-kloro-3,4-dihidroizokinolin-1-on;
5-kloro-3-metil-2-[5-[(1-propanoilazetidin-3-il)amino]piridin-3-il]-3H-izoindol-1-on;
5-kloro-2-[5-[(1-etilsulfonilazetidin-3-il)amino]piridin-3-il]-3-metil-3H-izoindol-1-on;
2-[5-[(2-acetil-2-azaspiro[3.3]heptan-6-il)amino]piridin-3-il]-5-kloro-3,3-dimetilizoindol-1-on;
5-kloro-3,3-dimetil-2-[5-[(2-propanoil-2-azaspiro[3.3]heptan-6-il)amino]piridin-3-il]izoindol-1-on;
5-kloro-2-[5-[(-2-etilsulfonil-2-azaspiro[3.3]heptan-6-il)amino]piridin-3-il]-3,3-dimetilizoindol-1-on;
5-kloro-3,3-dimetil-2-[5-[(2-propan-2-ilsulfonil-2-azaspiro[3.3]heptan-6-il)amino]piridin-3-il]izoindol-1-on;
(3R ili 3S)-5-kloro-3-metil-2-[5-[(1-propanoilazetidin-3-il)amino]-3-piridil]izoindolin-1-on;
(3S ili 3R)-5-kloro-3-metil-2-[5-[(1-propanoilazetidin-3-il)amino]-3-piridil]izoindolin-1-on;
(3R ili 3S)-5-kloro-2-[5-[(1-etilsulfonilazetidin-3-il)amino]-3-piridil]-3-metil-izoindolin-1-on;
(3S ili 3R)-5-kloro-2-[5-[(1-etilsulfonilazetidin-3-il)amino]-3-piridil]-3-metil-izoindolin-1-on;
2-[5-[(1-etilsulfonil-4-piperidil)amino]-3-piridil]-3,3-dimetil-1-okso-izoindolin-5-karbonitril;
3,3-dimetil-1-okso-2-[5-[(1-propanoil-4-piperidil)amino]-3-piridil]izoindolin-5-karbonitril;
3,3-dimetil-1-okso-2-[5-[(1-propanoilazetidin-3-il)amino]-3-piridil]izoindolin-5-karbonitril;
i njihove farmaceutski prihvatljive soli.
8. Spoj, naznačen time, da je odabran iz skupine koju čine
5-kloro-2-[5-[(1-etilsulfonilpiperidin-4-il)amino]piridin-3-il]-3,3-dimetilizoindol-1-on;
5-kloro-2-[5-[(1-etillsulfonilazetidin-3-il)amino]piridin-3-il]-3,3-dimetilizoindol-1-on;
5-kloro-3,3-dimetil-2-[5-[(1-propanoilazetidin-3-il)amino]piridin-3-il]izoindol-1-on;
5-kloro-3,3-dimetil-2-[5-[metil-[(3S ili 3R)-1-propan-2-ilsulfonilpirolidin-3-il]amino]piridin-3-il]izoindol-1-on;
5-kloro-3,3-dimetil-2-[5-[metil-[(3R ili 3S)-1-propan-2-ilsulfonilpirolidin-3-il]amino]piridin-3-il]izoindol-1-on;
5-kloro-3,3-dimetil-2-[5-[metil-[(3R ili 3S)-1-propilsulfonilpirolidin-3-il]amino]piridin-3-il]izoindol-1-on;
i njihove farmaceutski prihvatljive soli.
9. Spoj prema bilo kojem od patentnih zahtjeva 1 do 8, naznačen time, da je taj spoj
5-kloro-2-[5-[(1-etilsulfopiperidin-4-il)amino]piridin-3-il]-3,3-dimetilizoindol-1-on;
i njegove farmaceutski prihvatljive soli.
10. Postupak za proizvodnju spoja prema bilo kojem od patentnih zahtjeva 1 do 8, naznačen time, da obuhvaća
a) reakciju spoja formule (II) u prisutnosti spoja formule (III);
ili
b) reakciju spoja formule (IV) u prisutnosti spoja formule (V);
pri čemu su R1, R2, R7, R8, R9, R10, R11, R12, R13, R14, A, m, n i p definirani patentnim zahtjevom 1, dok je X u koraku a) halogen ili triflat, a u koraku b) je halogen.
11. Spoj prema bilo kojem od patentnih zahtjeva 1 do 8, naznačen time, da se koristi kao terapeutski aktivna tvar.
12. Farmaceutski pripravak, naznačen time, da sadrži spoj prema bilo kojem od patentnih zahtjeva 1 do 8 i terapeutski inertni nosač.
13. Spoj prema bilo kojem od patentnih zahtjeva 1 do 8, naznačen time, da se upotrebljava za liječenje ili profilaksu kronične bubrežne bolesti, kongestivnog zatajenja srca, visokog krvnog tlaka, primarnog aldosteronizma i Cushingovog sindroma.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN2013076281 | 2013-05-27 | ||
| EP14728131.5A EP3004077B1 (en) | 2013-05-27 | 2014-05-26 | New 3,4-dihydro-2h-isoquinoline-1-one and 2,3-dihydro-isoindol-1-one compounds |
| PCT/EP2014/060790 WO2014191338A1 (en) | 2013-05-27 | 2014-05-26 | New 3,4-dihydro-2h-isoquinoline-1-one and 2,3-dihydro-isoindol-1-one compounds |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| HRP20192275T1 true HRP20192275T1 (hr) | 2020-03-06 |
Family
ID=50884887
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HRP20192275TT HRP20192275T1 (hr) | 2013-05-27 | 2019-12-17 | Novi spojevi 3,4-dihidro-2h-izokinolin-1-ona i 2,3-dihidro-izoindol-1-ona |
Country Status (22)
| Country | Link |
|---|---|
| US (1) | US9695151B2 (hr) |
| EP (1) | EP3004077B1 (hr) |
| JP (2) | JP6416229B2 (hr) |
| KR (1) | KR102436885B1 (hr) |
| CN (1) | CN105143204B (hr) |
| AR (1) | AR096424A1 (hr) |
| BR (1) | BR112015028871B1 (hr) |
| CA (1) | CA2903180C (hr) |
| DK (1) | DK3004077T3 (hr) |
| ES (1) | ES2763338T3 (hr) |
| HK (1) | HK1213564A1 (hr) |
| HR (1) | HRP20192275T1 (hr) |
| HU (1) | HUE046773T2 (hr) |
| LT (1) | LT3004077T (hr) |
| MX (1) | MX370389B (hr) |
| PL (1) | PL3004077T3 (hr) |
| PT (1) | PT3004077T (hr) |
| RS (1) | RS59739B1 (hr) |
| RU (1) | RU2695524C2 (hr) |
| SI (1) | SI3004077T1 (hr) |
| TW (1) | TWI651317B (hr) |
| WO (1) | WO2014191338A1 (hr) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| HUE046773T2 (hu) * | 2013-05-27 | 2020-03-30 | Hoffmann La Roche | Új 3,4-dihidro-2H-izokinolin-1-on és 2,3-dihidro-izoindol-1-on vegyületek |
| JP6338658B2 (ja) | 2013-10-07 | 2018-06-06 | アンタレス・ファーマ・インコーポレーテッド | テストステロンの針補助ジェット注射を通じたヘマトクリット調節 |
| EA035185B1 (ru) * | 2014-10-08 | 2020-05-12 | Ф. Хоффманн-Ля Рош Аг | Производные спиродиамина в качестве ингибиторов альдостеронсинтазы |
| WO2019126559A1 (en) | 2017-12-20 | 2019-06-27 | Vanderbilt University | Antagonists of the muscarinic acetylcholine receptor m4 |
| RU2717310C1 (ru) * | 2019-06-04 | 2020-03-20 | Общество с ограниченной ответственностью "Таргет Медикалс" | Ингибиторы альдостеронсинтазы на основе производных 2-амино-4H-пиран-3-карбонитрила |
Family Cites Families (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| PT79699B (en) * | 1983-12-22 | 1986-12-10 | Pfizer | Process for preparing quinolone inotropic agents |
| CN85100796A (zh) * | 1985-04-01 | 1986-10-01 | 辉瑞公司 | 喹啉酮衍生物的制备方法 |
| DE102008022221A1 (de) * | 2008-05-06 | 2009-11-12 | Universität des Saarlandes | Inhibitoren der humanen Aldosteronsynthase CYP11B2 |
| US8541404B2 (en) * | 2009-11-09 | 2013-09-24 | Elexopharm Gmbh | Inhibitors of the human aldosterone synthase CYP11B2 |
| WO2012035078A1 (en) * | 2010-09-16 | 2012-03-22 | Novartis Ag | 17α-HYDROXYLASE/C17,20-LYASE INHIBITORS |
| CA2832996C (en) * | 2011-04-26 | 2019-05-07 | Merck Sharp & Dohme Corp. | Tricyclic triazole compounds and their use as aldosterone synthase inhibitors |
| AU2012307509B2 (en) * | 2011-09-15 | 2017-06-29 | F. Hoffmann-La Roche Ag | New dihydroquinoline-2-one derivatives |
| US9353081B2 (en) * | 2011-09-23 | 2016-05-31 | Hoffmann-La Roche Inc. | Bicyclic dihydroquinoline-2-one derivatives |
| PL3004076T3 (pl) * | 2013-05-27 | 2020-04-30 | F.Hoffmann-La Roche Ag | Nowe związki 3,4-dihydro-2h-izochinolin-1-onowe i 2,3-dihydroizoindol-1-onowe |
| HUE046773T2 (hu) * | 2013-05-27 | 2020-03-30 | Hoffmann La Roche | Új 3,4-dihidro-2H-izokinolin-1-on és 2,3-dihidro-izoindol-1-on vegyületek |
-
2014
- 2014-05-26 HU HUE14728131A patent/HUE046773T2/hu unknown
- 2014-05-26 CA CA2903180A patent/CA2903180C/en active Active
- 2014-05-26 ES ES14728131T patent/ES2763338T3/es active Active
- 2014-05-26 RS RS20191657A patent/RS59739B1/sr unknown
- 2014-05-26 JP JP2016515759A patent/JP6416229B2/ja active Active
- 2014-05-26 DK DK14728131.5T patent/DK3004077T3/da active
- 2014-05-26 KR KR1020157033719A patent/KR102436885B1/ko active IP Right Grant
- 2014-05-26 CN CN201480023886.XA patent/CN105143204B/zh active Active
- 2014-05-26 SI SI201431437T patent/SI3004077T1/sl unknown
- 2014-05-26 BR BR112015028871-5A patent/BR112015028871B1/pt active IP Right Grant
- 2014-05-26 TW TW103118318A patent/TWI651317B/zh active
- 2014-05-26 PT PT147281315T patent/PT3004077T/pt unknown
- 2014-05-26 RU RU2015150287A patent/RU2695524C2/ru active
- 2014-05-26 MX MX2015015010A patent/MX370389B/es active IP Right Grant
- 2014-05-26 WO PCT/EP2014/060790 patent/WO2014191338A1/en active Application Filing
- 2014-05-26 AR ARP140102072A patent/AR096424A1/es active IP Right Grant
- 2014-05-26 PL PL14728131T patent/PL3004077T3/pl unknown
- 2014-05-26 LT LTEP14728131.5T patent/LT3004077T/lt unknown
- 2014-05-26 EP EP14728131.5A patent/EP3004077B1/en active Active
-
2015
- 2015-11-20 US US14/947,760 patent/US9695151B2/en active Active
-
2016
- 2016-02-11 HK HK16101513.8A patent/HK1213564A1/zh unknown
-
2018
- 2018-10-03 JP JP2018188242A patent/JP6670906B2/ja active Active
-
2019
- 2019-12-17 HR HRP20192275TT patent/HRP20192275T1/hr unknown
Also Published As
| Publication number | Publication date |
|---|---|
| KR102436885B1 (ko) | 2022-08-26 |
| CA2903180A1 (en) | 2014-12-04 |
| JP6670906B2 (ja) | 2020-03-25 |
| EP3004077B1 (en) | 2019-10-30 |
| TWI651317B (zh) | 2019-02-21 |
| TW201533037A (zh) | 2015-09-01 |
| US20160075687A1 (en) | 2016-03-17 |
| PL3004077T3 (pl) | 2020-04-30 |
| HK1213564A1 (zh) | 2016-07-08 |
| RU2015150287A (ru) | 2017-06-28 |
| WO2014191338A1 (en) | 2014-12-04 |
| CN105143204A (zh) | 2015-12-09 |
| DK3004077T3 (da) | 2020-01-13 |
| SI3004077T1 (sl) | 2020-01-31 |
| HUE046773T2 (hu) | 2020-03-30 |
| JP2016520601A (ja) | 2016-07-14 |
| AR096424A1 (es) | 2015-12-30 |
| BR112015028871B1 (pt) | 2022-02-01 |
| LT3004077T (lt) | 2020-01-27 |
| RU2695524C2 (ru) | 2019-07-23 |
| BR112015028871A2 (pt) | 2017-07-25 |
| US9695151B2 (en) | 2017-07-04 |
| ES2763338T3 (es) | 2020-05-28 |
| MX370389B (es) | 2019-12-11 |
| PT3004077T (pt) | 2019-12-19 |
| CN105143204B (zh) | 2018-02-02 |
| MX2015015010A (es) | 2016-03-09 |
| RS59739B1 (sr) | 2020-02-28 |
| JP2019023212A (ja) | 2019-02-14 |
| JP6416229B2 (ja) | 2018-10-31 |
| CA2903180C (en) | 2022-03-15 |
| KR20160012145A (ko) | 2016-02-02 |
| EP3004077A1 (en) | 2016-04-13 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| HRP20192275T1 (hr) | Novi spojevi 3,4-dihidro-2h-izokinolin-1-ona i 2,3-dihidro-izoindol-1-ona | |
| RU2477723C2 (ru) | Ингибиторы протеинкиназ (варианты), их применение для лечения онкологических заболеваний и фармацевтическая композиция на их основе | |
| AR111314A1 (es) | Derivados de indolina sustituidos como inhibidores de la replicación vírica de dengue | |
| JP2018536648A5 (hr) | ||
| HRP20171028T1 (hr) | Indolski i indazolski spojevi koji aktiviraju ampk | |
| RU2017127135A (ru) | Терапевтическое средство против рака желчных протоков | |
| HRP20192242T1 (hr) | Novi spojevi 3,4-dihidro-2h-izokinolin-1-ona i 2,3-dihidro-izoindol-1-ona | |
| JP2014511892A5 (hr) | ||
| JP2016516699A5 (hr) | ||
| JP2007532651A5 (hr) | ||
| PE20171057A1 (es) | Derivados espirodiamina como inhibidores de la aldosterona sintasa | |
| RU2014103587A (ru) | Производные циклических аминов в качестве антагонистов рецептора ер4 | |
| JP2014533695A5 (hr) | ||
| JP2015505296A5 (hr) | ||
| EA201400553A1 (ru) | Производные 2-(1,2,3-триазол-2-ил)бензамида и 3-(1,2,3-триазол-2-ил)пиколинамида | |
| JP2017537949A5 (hr) | ||
| EA200901379A1 (ru) | Производные никотиновой кислоты как модуляторы метаботропных глутаматных рецепторов 5 подтипа | |
| EA201000805A1 (ru) | Бис-(сульфониламино)производные в терапии 066 | |
| RS54492B1 (en) | KINASE INHIBITOR REGULATING THE SIGNAL PATH OF APOPTOSIS | |
| JP2017505293A5 (hr) | ||
| RS54183B1 (en) | PIRAZOLE DERIVATIVES | |
| EA201492170A1 (ru) | Новые замещенные в цикле n-пиридиниламиды в качестве ингибиторов киназ | |
| CR20140462A (es) | Sales de 5-[(1r)-2-({2-[4-(2,2-difluoro-2-feniletoxi)fenil]etil} amino) -1-hidroxietil]-8-hidroquinolin-2(1h)-ona | |
| JP2011088926A5 (hr) | ||
| EA201792071A2 (ru) | Производные глутаримидов, их применение, фармацевтическая композиция на их основе, способы их получения |