HRP20180592T1 - Novi biciklički derivati dihidrokinolin-2-ona - Google Patents
Novi biciklički derivati dihidrokinolin-2-ona Download PDFInfo
- Publication number
- HRP20180592T1 HRP20180592T1 HRP20180592TT HRP20180592T HRP20180592T1 HR P20180592 T1 HRP20180592 T1 HR P20180592T1 HR P20180592T T HRP20180592T T HR P20180592TT HR P20180592 T HRP20180592 T HR P20180592T HR P20180592 T1 HRP20180592 T1 HR P20180592T1
- Authority
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- Croatia
- Prior art keywords
- methyl
- tetrahydro
- oxo
- propionamide
- isoquinolin
- Prior art date
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- 125000002619 bicyclic group Chemical group 0.000 title 1
- 229940080818 propionamide Drugs 0.000 claims 31
- 150000001875 compounds Chemical class 0.000 claims 24
- QLNJFJADRCOGBJ-UHFFFAOYSA-N propionamide Chemical compound CCC(N)=O QLNJFJADRCOGBJ-UHFFFAOYSA-N 0.000 claims 13
- 150000003839 salts Chemical class 0.000 claims 10
- VDEUDSRUMNAXJG-LJQANCHMSA-N n-[(8r)-4-(1-methyl-2-oxo-3,4-dihydroquinolin-6-yl)-5,6,7,8-tetrahydroisoquinolin-8-yl]propanamide Chemical compound CN1C(=O)CCC2=CC(C3=CN=CC4=C3CCC[C@H]4NC(=O)CC)=CC=C21 VDEUDSRUMNAXJG-LJQANCHMSA-N 0.000 claims 6
- RSOJSFYJLQADDM-UHFFFAOYSA-N ethanesulfonamide Chemical compound [CH2]CS(N)(=O)=O RSOJSFYJLQADDM-UHFFFAOYSA-N 0.000 claims 4
- LVDKZTHQIJVVBW-UHFFFAOYSA-N n-[4-(1-methyl-2-oxo-3,4-dihydroquinolin-6-yl)-5,6,7,8-tetrahydroisoquinolin-8-yl]ethanesulfonamide Chemical compound CN1C(=O)CCC2=CC(C3=CN=CC4=C3CCCC4NS(=O)(=O)CC)=CC=C21 LVDKZTHQIJVVBW-UHFFFAOYSA-N 0.000 claims 4
- VDEUDSRUMNAXJG-UHFFFAOYSA-N n-[4-(1-methyl-2-oxo-3,4-dihydroquinolin-6-yl)-5,6,7,8-tetrahydroisoquinolin-8-yl]propanamide Chemical compound CN1C(=O)CCC2=CC(C3=CN=CC4=C3CCCC4NC(=O)CC)=CC=C21 VDEUDSRUMNAXJG-UHFFFAOYSA-N 0.000 claims 4
- RTZNXQJJCMMOPY-UHFFFAOYSA-N n-[4-(1-methyl-2-oxo-3,4-dihydroquinolin-6-yl)-6,7-dihydro-5h-cyclopenta[c]pyridin-7-yl]propanamide Chemical compound CN1C(=O)CCC2=CC(C3=CN=CC4=C3CCC4NC(=O)CC)=CC=C21 RTZNXQJJCMMOPY-UHFFFAOYSA-N 0.000 claims 4
- 125000006701 (C1-C7) alkyl group Chemical group 0.000 claims 3
- 229910052736 halogen Inorganic materials 0.000 claims 3
- 150000002367 halogens Chemical group 0.000 claims 3
- 229910052739 hydrogen Inorganic materials 0.000 claims 3
- 239000001257 hydrogen Substances 0.000 claims 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 2
- -1 hydroxyl-C1-C7-alkyl Chemical group 0.000 claims 2
- YBWKRNZJXVKUQC-UHFFFAOYSA-N n-[2-[5-(1-methyl-2-oxo-3,4-dihydroquinolin-6-yl)-3,4-dihydro-2h-1,7-naphthyridin-1-yl]ethyl]propanamide Chemical compound CN1C(=O)CCC2=CC(C3=CN=CC4=C3CCCN4CCNC(=O)CC)=CC=C21 YBWKRNZJXVKUQC-UHFFFAOYSA-N 0.000 claims 2
- ICJMGJBNROMRTB-UHFFFAOYSA-N n-[4-(1-methyl-2-oxo-3,4-dihydroquinolin-6-yl)-6,7-dihydro-5h-cyclopenta[c]pyridin-7-yl]ethanesulfonamide Chemical compound CN1C(=O)CCC2=CC(C3=CN=CC4=C3CCC4NS(=O)(=O)CC)=CC=C21 ICJMGJBNROMRTB-UHFFFAOYSA-N 0.000 claims 2
- 239000000825 pharmaceutical preparation Substances 0.000 claims 2
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims 1
- DQSZXHUFCGFADZ-UHFFFAOYSA-N 1-methyl-6-(8-oxo-6,7-dihydro-5h-isoquinolin-4-yl)-3,4-dihydroquinolin-2-one Chemical compound O=C1CCCC2=C1C=NC=C2C1=CC=C2N(C)C(=O)CCC2=C1 DQSZXHUFCGFADZ-UHFFFAOYSA-N 0.000 claims 1
- ZRGHMSFUQOKWOP-OAQYLSRUSA-N 3-chloro-n-[(8r)-4-(1-methyl-2-oxo-3,4-dihydroquinolin-6-yl)-5,6,7,8-tetrahydroisoquinolin-8-yl]pyridine-2-carboxamide Chemical compound N([C@H]1C=2C=NC=C(C=2CCC1)C=1C=C2CCC(=O)N(C2=CC=1)C)C(=O)C1=NC=CC=C1Cl ZRGHMSFUQOKWOP-OAQYLSRUSA-N 0.000 claims 1
- JKGUWJPSQLGLQF-UHFFFAOYSA-N 6-(8-hydroxy-5,6,7,8-tetrahydroisoquinolin-4-yl)-1-methyl-3,4-dihydroquinolin-2-one Chemical compound OC1CCCC2=C1C=NC=C2C1=CC=C2N(C)C(=O)CCC2=C1 JKGUWJPSQLGLQF-UHFFFAOYSA-N 0.000 claims 1
- PNXQJOWNYRUIIT-QGZVFWFLSA-N 6-[(8r)-8-amino-5,6,7,8-tetrahydroisoquinolin-4-yl]-1-methyl-3,4-dihydroquinolin-2-one Chemical compound N[C@@H]1CCCC2=C1C=NC=C2C1=CC=C2N(C)C(=O)CCC2=C1 PNXQJOWNYRUIIT-QGZVFWFLSA-N 0.000 claims 1
- DPMMXCYALCMNFT-UHFFFAOYSA-N 6-[1-(2-aminoethyl)-3,4-dihydro-2h-1,7-naphthyridin-5-yl]-1-methyl-3,4-dihydroquinolin-2-one;hydrochloride Chemical compound Cl.NCCN1CCCC2=C1C=NC=C2C1=CC=C2N(C)C(=O)CCC2=C1 DPMMXCYALCMNFT-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
- 125000004432 carbon atom Chemical group C* 0.000 claims 1
- 208000020832 chronic kidney disease Diseases 0.000 claims 1
- 150000002148 esters Chemical class 0.000 claims 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 1
- 150000002431 hydrogen Chemical group 0.000 claims 1
- RTZNXQJJCMMOPY-GOSISDBHSA-N n-[(7r)-4-(1-methyl-2-oxo-3,4-dihydroquinolin-6-yl)-6,7-dihydro-5h-cyclopenta[c]pyridin-7-yl]propanamide Chemical compound CN1C(=O)CCC2=CC(C3=CN=CC4=C3CC[C@H]4NC(=O)CC)=CC=C21 RTZNXQJJCMMOPY-GOSISDBHSA-N 0.000 claims 1
- RTZNXQJJCMMOPY-SFHVURJKSA-N n-[(7s)-4-(1-methyl-2-oxo-3,4-dihydroquinolin-6-yl)-6,7-dihydro-5h-cyclopenta[c]pyridin-7-yl]propanamide Chemical compound CN1C(=O)CCC2=CC(C3=CN=CC4=C3CC[C@@H]4NC(=O)CC)=CC=C21 RTZNXQJJCMMOPY-SFHVURJKSA-N 0.000 claims 1
- FVDLJNMIWFGZAM-LJQANCHMSA-N n-[(8r)-4-(1-methyl-2-oxo-3,4-dihydroquinolin-6-yl)-5,6,7,8-tetrahydroisoquinolin-8-yl]acetamide Chemical compound CC(=O)N[C@@H]1CCCC2=C1C=NC=C2C1=CC=C2N(C)C(=O)CCC2=C1 FVDLJNMIWFGZAM-LJQANCHMSA-N 0.000 claims 1
- RDQPEYCXPWXJGF-HXUWFJFHSA-N n-[(8r)-4-(1-methyl-2-oxo-3,4-dihydroquinolin-6-yl)-5,6,7,8-tetrahydroisoquinolin-8-yl]cyclopropanecarboxamide Chemical compound N([C@H]1C=2C=NC=C(C=2CCC1)C=1C=C2CCC(=O)N(C2=CC=1)C)C(=O)C1CC1 RDQPEYCXPWXJGF-HXUWFJFHSA-N 0.000 claims 1
- UCOSNKRUHVSIHZ-HXUWFJFHSA-N n-[(8r)-4-(1-methyl-2-oxo-3,4-dihydroquinolin-6-yl)-5,6,7,8-tetrahydroisoquinolin-8-yl]cyclopropanesulfonamide Chemical compound N([C@H]1C=2C=NC=C(C=2CCC1)C=1C=C2CCC(=O)N(C2=CC=1)C)S(=O)(=O)C1CC1 UCOSNKRUHVSIHZ-HXUWFJFHSA-N 0.000 claims 1
- LVDKZTHQIJVVBW-LJQANCHMSA-N n-[(8r)-4-(1-methyl-2-oxo-3,4-dihydroquinolin-6-yl)-5,6,7,8-tetrahydroisoquinolin-8-yl]ethanesulfonamide Chemical compound CN1C(=O)CCC2=CC(C3=CN=CC4=C3CCC[C@H]4NS(=O)(=O)CC)=CC=C21 LVDKZTHQIJVVBW-LJQANCHMSA-N 0.000 claims 1
- LGECSSVAXLBSOF-GOSISDBHSA-N n-[(8r)-4-(1-methyl-2-oxo-3,4-dihydroquinolin-6-yl)-5,6,7,8-tetrahydroisoquinolin-8-yl]methanesulfonamide Chemical compound CS(=O)(=O)N[C@@H]1CCCC2=C1C=NC=C2C1=CC=C2N(C)C(=O)CCC2=C1 LGECSSVAXLBSOF-GOSISDBHSA-N 0.000 claims 1
- LVDKZTHQIJVVBW-IBGZPJMESA-N n-[(8s)-4-(1-methyl-2-oxo-3,4-dihydroquinolin-6-yl)-5,6,7,8-tetrahydroisoquinolin-8-yl]ethanesulfonamide Chemical compound CN1C(=O)CCC2=CC(C3=CN=CC4=C3CCC[C@@H]4NS(=O)(=O)CC)=CC=C21 LVDKZTHQIJVVBW-IBGZPJMESA-N 0.000 claims 1
- VDEUDSRUMNAXJG-IBGZPJMESA-N n-[(8s)-4-(1-methyl-2-oxo-3,4-dihydroquinolin-6-yl)-5,6,7,8-tetrahydroisoquinolin-8-yl]propanamide Chemical compound CN1C(=O)CCC2=CC(C3=CN=CC4=C3CCC[C@@H]4NC(=O)CC)=CC=C21 VDEUDSRUMNAXJG-IBGZPJMESA-N 0.000 claims 1
- HAICWNWRAUVVBM-UHFFFAOYSA-N n-[4-(1-methyl-2-oxo-3,4-dihydroquinolin-6-yl)-5,6-dihydroisoquinolin-8-yl]propanamide Chemical compound CN1C(=O)CCC2=CC(C3=CN=CC4=C3CCC=C4NC(=O)CC)=CC=C21 HAICWNWRAUVVBM-UHFFFAOYSA-N 0.000 claims 1
- GDFFFZVMFMXFKF-UHFFFAOYSA-N n-[4-(7-chloro-1-methyl-2-oxo-3,4-dihydroquinolin-6-yl)-5,6,7,8-tetrahydroisoquinolin-8-yl]ethanesulfonamide Chemical compound C1CC(=O)N(C)C(C=C2Cl)=C1C=C2C1=CN=CC2=C1CCCC2NS(=O)(=O)CC GDFFFZVMFMXFKF-UHFFFAOYSA-N 0.000 claims 1
- CIRJNKSQEGVMOH-UHFFFAOYSA-N n-[4-(7-fluoro-1-methyl-2-oxo-3,4-dihydroquinolin-6-yl)-5,6,7,8-tetrahydroisoquinolin-8-yl]propanamide Chemical compound C1CC(=O)N(C)C(C=C2F)=C1C=C2C1=CN=CC2=C1CCCC2NC(=O)CC CIRJNKSQEGVMOH-UHFFFAOYSA-N 0.000 claims 1
- ZXBMXHVGJUPJTE-UHFFFAOYSA-N n-[4-(7-fluoro-1-methyl-2-oxo-3,4-dihydroquinolin-6-yl)-6,7-dihydro-5h-cyclopenta[c]pyridin-7-yl]ethanesulfonamide Chemical compound C1CC(=O)N(C)C(C=C2F)=C1C=C2C1=CN=CC2=C1CCC2NS(=O)(=O)CC ZXBMXHVGJUPJTE-UHFFFAOYSA-N 0.000 claims 1
- RXJOFZNMHGDABT-UHFFFAOYSA-N n-[4-(7-fluoro-1-methyl-2-oxo-3,4-dihydroquinolin-6-yl)-6,7-dihydro-5h-cyclopenta[c]pyridin-7-yl]propanamide Chemical compound C1CC(=O)N(C)C(C=C2F)=C1C=C2C1=CN=CC2=C1CCC2NC(=O)CC RXJOFZNMHGDABT-UHFFFAOYSA-N 0.000 claims 1
- HSGKLAIGXVMJHK-UHFFFAOYSA-N n-[4-(8-chloro-1-methyl-2-oxo-3,4-dihydroquinolin-6-yl)-5,6,7,8-tetrahydroisoquinolin-8-yl]ethanesulfonamide Chemical compound CN1C(=O)CCC2=CC(C3=CN=CC4=C3CCCC4NS(=O)(=O)CC)=CC(Cl)=C21 HSGKLAIGXVMJHK-UHFFFAOYSA-N 0.000 claims 1
- PYDLSXYBCSOQEO-UHFFFAOYSA-N n-[4-(8-chloro-1-methyl-2-oxo-3,4-dihydroquinolin-6-yl)-5,6,7,8-tetrahydroisoquinolin-8-yl]propanamide Chemical compound CN1C(=O)CCC2=CC(C3=CN=CC4=C3CCCC4NC(=O)CC)=CC(Cl)=C21 PYDLSXYBCSOQEO-UHFFFAOYSA-N 0.000 claims 1
- VAPHWOXHHBPQER-UHFFFAOYSA-N n-[4-(8-chloro-1-methyl-2-oxo-3,4-dihydroquinolin-6-yl)-6,7-dihydro-5h-cyclopenta[c]pyridin-7-yl]propanamide Chemical compound CN1C(=O)CCC2=CC(C3=CN=CC4=C3CCC4NC(=O)CC)=CC(Cl)=C21 VAPHWOXHHBPQER-UHFFFAOYSA-N 0.000 claims 1
- PRAVHWYRPCMUPQ-UHFFFAOYSA-N n-[4-(8-fluoro-1-methyl-2-oxo-3,4-dihydroquinolin-6-yl)-5,6,7,8-tetrahydroisoquinolin-8-yl]ethanesulfonamide Chemical compound CN1C(=O)CCC2=CC(C3=CN=CC4=C3CCCC4NS(=O)(=O)CC)=CC(F)=C21 PRAVHWYRPCMUPQ-UHFFFAOYSA-N 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
- JQACWJRUDPWMEO-UHFFFAOYSA-N tert-butyl n-[2-[5-(1-methyl-2-oxo-3,4-dihydroquinolin-6-yl)-3,4-dihydro-2h-1,7-naphthyridin-1-yl]ethyl]carbamate Chemical compound CC(C)(C)OC(=O)NCCN1CCCC2=C1C=NC=C2C1=CC=C2N(C)C(=O)CCC2=C1 JQACWJRUDPWMEO-UHFFFAOYSA-N 0.000 claims 1
- 238000011282 treatment Methods 0.000 claims 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
- A61P3/10—Drugs for disorders of the metabolism for glucose homeostasis for hyperglycaemia, e.g. antidiabetics
-
- 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
- A61P5/00—Drugs for disorders of the endocrine system
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- 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
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- 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
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- 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
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- 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
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- 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
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- 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
- C07D401/04—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
-
- 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
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- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
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- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
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- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Diabetes (AREA)
- Cardiology (AREA)
- Endocrinology (AREA)
- Heart & Thoracic Surgery (AREA)
- Hospice & Palliative Care (AREA)
- Emergency Medicine (AREA)
- Hematology (AREA)
- Obesity (AREA)
- Urology & Nephrology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Claims (20)
1. Spojevi, naznačeni time, da su predstavljeni formulom (I)
[image]
u kojoj
R1 je C1-C7-alkil;
R2 je H;
R3 je H;
R4 je H;
R5 je H;
R6 je vodik, halogen ili C1-C7-alkil;
R7 je H;
R8 je H;
R9 je H;
R10 je H;
R11 je H;
R12 je vodik ili halogen;
A1 je CR13;
A2 je NR14 ili CR15R16;
A3 je CR17;
R13 je vodik ili halogen;
R14 je -(CR20R21)q-(CR22R23)r-(CR24R25)p-NR26R27, pri čemu zbroj q, r i p iznosi najmanje 2;
R15 je -(CR20R21)q-(CR22R23)r-(CR24R25)p-NR26R27;
R16 je H;
ili R6 i R16 zajedno s ugljikovim atomima s kojima su spojeni, tvore dvostruku vezu;
R17 je H;
R20 je H;
R21 je H;
R22 je H;
R23 je H;
R24 je H;
R25 je H;
R26 je H;
R27 je H, -S(O)2R31, -C(O)R31 ili -C(O)OR31, pri čemu u slučaju da R26 je H i R27je H, tada zbroj q, r i p iznosi najmanje 1;
R31 je C1-C7-alkil, hidroksil-C1-C7-alkil, C3-C8-cikloalkil ili kloropiridinil;
n je nula ili 1;
p je nula ili 1;
q je nula ili 1;
r je nula ili 1;
ili farmaceutski prihvatljive soli ili esteri.
2. Spoj prema zahtjevu 1, naznačen time, da R6 je H.
3. Spoj prema bilo kojem od patentnih zahtjeva 1 do 2, naznačen time, da R12 je H.
4. Spoj prema bilo kojem od patentnih zahtjeva 1 do 3, naznačen time, da A2 je CR15R16.
5. Spoj prema bilo kojem od patentnih zahtjeva 1 do 4, naznačen time, da R27 je -C(O)R31.
6. Spoj prema bilo kojem od patentnih zahtjeva 1 do 5, naznačen time, da R31 je C1-C7-alkil.
7. Spoj prema bilo kojem od patentnih zahtjeva 1 do 6, naznačen time, da n je 1.
8. Spoj prema bilo kojem od patentnih zahtjeva 1 do 7, naznačen time, da su q, r i p nula.
9. Spoj prema bilo kojem od patentnih zahtjeva 1 do 8, naznačen time, da je odabran iz skupine koju čine:
(rac)-N-[4-(1-metil-2-okso-1,2,3,4-tetrahidro-kinolin-6-il)-5,6,7,8-tetrahidro-izokinolin-8-il]-propionamid;
(-)-N-(4-(1-metil-2-okso-1,2,3,4-tetrahidrokinolin-6-il)-5,6,7,8-tetrahidroizokinolin-8-il)propionamid;
(+)-N-(4-(1-metil-2-okso-1,2,3,4-tetrahidrokinolin-6-il)-5,6,7,8-tetrahidroizokinolin-8-il)propionamid;
(R)-N-(4-(1-metil-2-okso-1,2,3,4-tetrahidrokinolin-6-il)-5,6,7,8-tetrahidroizokinolin-8-il)propionamid;
(S)-N-(4-(1-metil-2-okso-1,2,3,4-tetrahidrokinolin-6-il)-5,6,7,8-tetrahidroizokinolin-8-il)propionamid;
(rac)-N-(4-(1-metil-2-okso-1,2,3,4-tetrahidrokinolin-6-il)-5,6,7,8-tetrahidroizokinolin-8-il)etansulfonamid;
(-)-N-(4-(1-metil-2-okso-1,2,3,4-tetrahidrokinolin-6-il)-5,6,7,8-tetrahidroizokinolin-8-il)etansulfonamid;
(+)-N-(4-(1-metil-2-okso-1,2,3,4-tetrahidrokinolin-6-il)-5,6,7,8-tetrahidroizokinolin-8-il)etansulfonamid;
(R)-N-(4-(1-metil-2-okso-1,2,3,4-tetrahidrokinolin-6-il)-5,6,7,8-tetrahidroizokinolin-8-il)etansulfonamid;
(S)-N-(4-(1-metil-2-okso-1,2,3,4-tetrahidrokinolin-6-il)-5,6,7,8-tetrahidroizokinolin-8-il)etansulfonamid;
(rac)-N-(4-(1-metil-2-okso-1,2,3,4-tetrahidrokinolin-6-il)-6,7-dihidro-5H-ciklopenta[c]piridin-7-il)propionamid;
(-)-N-(4-(1-metil-2-okso-1,2,3,4-tetrahidrokinolin-6-il)-6,7-dihidro-5H-ciklopenta[c]piridin-7-il)propionamid;
(+)-N-(4-(1-metil-2-okso-1,2,3,4-tetrahidrokinolin-6-il)-6,7-dihidro-5H-ciklopenta[c]piridin-7-il)propionamid;
(R)-N-(4-(1-metil-2-okso-1,2,3,4-tetrahidrokinolin-6-il)-6,7-dihidro-5H-ciklopenta[c]piridin-7-il)propionamid;
(S)-N-(4-(1-metil-2-okso-1,2,3,4-tetrahidrokinolin-6-il)-6,7-dihidro-5H-ciklopenta[c]piridin-7-il)propionamid;
(rac)-N-(4-(1-metil-2-okso-1,2,3,4-tetrahidrokinolin-6-il)-6,7-dihidro-5H-ciklopenta[c]piridin-7-il)etansulfonamid;
{2-[5-(1-metil-2-okso-1,2,3,4-tetrahidro-kinolin-6-il)-3,4-dihidro-2H-[1,7]naftiridin-1-il]-etil}-karbaminska kiselina- terc-butil ester;
6-[1-(2-amino-etil)-1,2,3,4-tetrahidro-[1,7]naftiridin-5-il]-1-metil-3,4-dihidro-1H-kinolin-2-on- hidroklorid;
N-{2-[5-(1-metil-2-okso-1,2,3,4-tetrahidro-kinolin-6-il)-3,4-dihidro-2H-[1,7]naftiridin-1-il]-etil}-propionamid;
N-(2-(5-(1-metil-2-okso-1,2,3,4-tetrahidrokinolin-6-il)-3,4-dihidro-1,7-naftiridin-1(2H)-il)etil)etansulfonamid;
i njihove farmaceutski prihvatljive soli.
10. Spoj prema bilo kojem od patentnih zahtjeva 1 do 8, naznačen time, da je odabran iz skupine koju čine:
(2R,S)-2-hidroksi-N-((4R,S)-4-(1-metil-2-okso-1,2,3,4-tetrahidrokinolin-6-il)-5,6,7,8-tetrahidroizokinolin-8-il)propanamid;
(2R)-2-hidroksi-N-((4R,S)-4-(1-metil-2-okso-1,2,3,4-tetrahidrokinolin-6-il)-5,6,7,8-tetrahidroizokinolin-8-il)propanamid;
(2S)-2-hidroksi-N-((4R,S)-4-(1-metil-2-okso-1,2,3,4-tetrahidrokinolin-6-il)-5,6,7,8-tetrahidroizokinolin-8-il)propanamid;
(+)-(2R)-2-hidroksi-N-((4R ili 4S)-4-(1-metil-2-okso-1,2,3,4-tetrahidrokinolin-6-il)-5,6,7,8-tetrahidroizokinolin-8-il)propanamid;
(-)-(2R)-2-hidroksi-N-((4S ili 4R)-4-(1-metil-2-okso-1,2,3,4-tetrahidrokinolin-6-il)-5,6,7,8-tetrahidroizokinolin-8-il)propanamid;
(-)-(2S)-2-hidroksi-N-((4S ili 4R)-4-(1-metil-2-okso-1,2,3,4-tetrahidrokinolin-6-il)-5,6,7,8-tetrahidroizokinolin-8-il)propanamid;
(+)-(2S)-2-hidroksi-N-((4R ili 4S)-4-(1-metil-2-okso-1,2,3,4-tetrahidrokinolin-6-il)-5,6,7,8-tetrahidroizokinolin-8-il)propanamid;
(rac)-N-(4-(7-fluoro-1-metil-2-okso-1,2,3,4-tetrahidrokinolin-6-il)-6,7-dihidro-5H-ciklopenta[c]piridin-7-il)propionamid;
(-)-(S ili R)-N-(4-(7-fluoro-1-metil-2-okso-1,2,3,4-tetrahidrokinolin-6-il)-6,7-dihidro-5H-ciklopenta[c]piridin-7-il)propionamid;
(+)-(R ili S)-N-(4-(7-fluoro-1-metil-2-okso-1,2,3,4-tetrahidrokinolin-6-il)-6,7-dihidro-5H-ciklopenta[c]piridin-7-il)propionamid;
(rac)-N-(4-(7-fluoro-1-metil-2-okso-1,2,3,4-tetrahidrokinolin-6-il)-6,7-dihidro-5H-ciklopenta[c]piridin-7-il)etansulfonamid;
(-)-(S ili R)-N-(4-(7-fluoro-1-metil-2-okso-1,2,3,4-tetrahidrokinolin-6-il)-6,7-dihidro-5H-ciklopenta[c]piridin-7-il)etansulfonamid;
(+)-(R ili S)-N-(4-(7-fluoro-1-metil-2-okso-1,2,3,4-tetrahidrokinolin-6-il)-6,7-dihidro-5H-ciklopenta[c]piridin-7-il)etansulfonamid;
(rac)-N-[4-(7-fluoro-1-metil-2-okso-1,2,3,4-tetrahidro-kinolin-6-il)-5,6,7,8-tetrahidro-izokinolin-8-il]-propionamid;
(-)-(S ili R)-N-[4-(7-fluoro-1-metil-2-okso-1,2,3,4-tetrahidro-kinolin-6-il)-5,6,7,8-tetrahidro-izokinolin-8-il]-propionamid;
(+)-(R ili S)-N-[4-(7-fluoro-1-metil-2-okso-1,2,3,4-tetrahidro-kinolin-6-il)-5,6,7,8-tetrahidro-izokinolin-8-il]-propionamid;
(-)-(S ili R)-etansulfonska kiselina-[4-(7-fluoro-1-metil-2-okso-1,2,3,4-tetrahidro-kinolin-6-il)-5,6,7,8-tetrahidro-izokinolin-8-il]-amid;
(+)-(R ili S)-etansulfonska kiselina-[4-(7-fluoro-1-metil-2-okso-1,2,3,4-tetrahidro-kinolin-6-il)-5,6,7,8-tetrahidro-izokinolin-8-il]-amid;
(rac)-N-[4-(8-kloro-1-metil-2-okso-1,2,3,4-tetrahidro-kinolin-6-il)-5,6,7,8-tetrahidro-izokinolin-8-il]-propionamid;
(rac)-etansulfonska kiselina-[4-(7-kloro-1-metil-2-okso-1,2,3,4-tetrahidro-kinolin-6-il)-5,6,7,8-tetrahidro-izokinolin-8-il]-amid;
N-[(R ili S)-4-(7-kloro-1-metil-2-okso-1,2,3,4-tetrahidro-kinolin-6-il)-5,6,7,8-tetrahidro-izokinolin-8-il]-propionamid;
(rac)-etansulfonska kiselina-[4-(8-fluoro-1-metil-2-okso-1,2,3,4-tetrahidro-kinolin-6-il)-5,6,7,8-tetrahidro-izokinolin-8-il]-amid;
(rac)-etansulfonska kiselina-[4-(8-kloro-1-metil-2-okso-1,2,3,4-tetrahidro-kinolin-6-il)-5,6,7,8-tetrahidro-izokinolin-8-il]-amid;
(+)-etansulfonska kiselina-[(R ili S)-4-(8-kloro-1-metil-2-okso-1,2,3,4-tetrahidro-kinolin-6-il)-5,6,7,8-tetrahidro-izokinolin-8-il]-amid;
(-)-etansulfonska kiselina-[(S ili R)-4-(8-kloro-1-metil-2-okso-1,2,3,4-tetrahidro-kinolin-6-il)-5,6,7,8-tetrahidro-izokinolin-8-il]-amid;
(-)-N-[(S ili R)-4-(8-kloro-1-metil-2-okso-1,2,3,4-tetrahidro-kinolin-6-il)-5,6,7,8-tetrahidro-izokinolin-8-il]-propionamid;
(+)-N-[(R ili S)-4-(8-kloro-1-metil-2-okso-1,2,3,4-tetrahidro-kinolin-6-il)-5,6,7,8-tetrahidro-izokinolin-8-il]-propionamid;
(+)-N-[(7S,8R ili 7R,8S)-7-metil-4-(1-metil-2-okso-1,2,3,4-tetrahidro-kinolin-6-il)-5,6,7,8-tetrahidro-izokinolin-8-il]-propionamid;
(-)-N-[(7S,8S ili 7R,8R)-4-(7-fluoro-1-metil-2-okso-1,2,3,4-tetrahidro-kinolin-6-il)-7-metil-5,6,7,8-tetrahidro-izokinolin-8-il]-propionamid;
(-)-N-[(7R,8S ili 7S,8R)-4-(7-fluoro-1-metil-2-okso-1,2,3,4-tetrahidro-kinolin-6-il)-7-metil-5,6,7,8-tetrahidro-izokinolin-8-il]-propionamid;
(+)-N-[(7S,8R ili 7R,8S)-4-(7-fluoro-1-metil-2-okso-1,2,3,4-tetrahidro-kinolin-6-il)-7-metil-5,6,7,8-tetrahidro-izokinolin-8-il]-propionamid;
(-)-N-[(7S,8S ili 7R,8R)-7-metil-4-(1-metil-2-okso-1,2,3,4-tetrahidro-kinolin-6-il)-5,6,7,8-tetrahidro-izokinolin-8-il]-propionamid;
(-)-N-[(7R,8S ili 7S,8R)-7-metil-4-(1-metil-2-okso-1,2,3,4-tetrahidro-kinolin-6-il)-5,6,7,8-tetrahidro-izokinolin-8-il]-propionamid;
(+)-N-[(7R,8R ili 7S,8S)-4-(7-fluoro-1-metil-2-okso-1,2,3,4-tetrahidro-kinolin-6-il)-7-metil-5,6,7,8-tetrahidro-izokinolin-8-il]-propionamid;
(+)-N-[(7R,8R ili 7S,8S)-7-metil-4-(1-metil-2-okso-1,2,3,4-tetrahidro-kinolin-6-il)-5,6,7,8-tetrahidro-izokinolin-8-il]-propionamid;
(-)-N-[(7R,8R ili 7S,8S)-7-fluoro-4-(1-metil-2-okso-1,2,3,4-tetrahidro-kinolin-6-il)-5,6,7,8-tetrahidro-izokinolin-8-il]-propionamid;
(-)-N-[(7S,8R ili 7R,8S)-7-fluoro-4-(1-metil-2-okso-1,2,3,4-tetrahidro-kinolin-6-il)-5,6,7,8-tetrahidro-izokinolin-8-il]-propionamid;
(+)-N-[(7S,8S ili 7R,8R)-7-fluoro-4-(1-metil-2-okso-1,2,3,4-tetrahidro-kinolin-6-il)-5,6,7,8-tetrahidro-izokinolin-8-il]-propionamid;
(+)-N-[(7R,8S ili 7S,8R)-7-fluoro-4-(1-metil-2-okso-1,2,3,4-tetrahidro-kinolin-6-il)-5,6,7,8-tetrahidro-izokinolin-8-il]-propionamid;
(+)-N-[(7S,8S ili 7R,8R)-7-fluoro-4-(7-fluoro-1-metil-2-okso-1,2,3,4-tetrahidro-kinolin-6-il)-5,6,7,8-tetrahidro-izokinolin-8-il]-propionamid;
(+)-N-[(7R,8S ili 7S,8R)-7-fluoro-4-(7-fluoro-1-metil-2-okso-1,2,3,4-tetrahidro-kinolin-6-il)-5,6,7,8-tetrahidro-izokinolin-8-il]-propionamid;
(-)-N-[(7R,8R ili 7S,8S)-7-fluoro-4-(7-fluoro-1-metil-2-okso-1,2,3,4-tetrahidro-kinolin-6-il)-5,6,7,8-tetrahidro-izokinolin-8-il]-propionamid;
(-)-N-[(7S,8R ili 7R,8S)-7-fluoro-4-(7-fluoro-1-metil-2-okso-1,2,3,4-tetrahidro-kinolin-6-il)-5,6,7,8-tetrahidro-izokinolin-8-il]-propionamid;
(rac)-N-(4-(8-kloro-1-metil-2-okso-1,2,3,4-tetrahidrokinolin-6-il)-6,7-dihidro-5H-ciklopenta[c]piridin-7-il)propionamid;
(-)-(S ili R)-N-(4-(8-kloro-1-metil-2-okso-1,2,3,4-tetrahidrokinolin-6-il)-6,7-dihidro-5H-ciklopenta[c]piridin-7-il)propionamid;
(+)-(R ili S)-N-(4-(8-kloro-1-metil-2-okso-1,2,3,4-tetrahidrokinolin-6-il)-6,7-dihidro-5H-ciklopenta[c]piridin-7-il)propionamid;
(R)-6-(8-amino-5,6,7,8-tetrahidroizokinolin-4-il)-1-metil-3,4-dihidrokinolin-2(1H)-on;
3-kloro-piridin-2-karboksilna kiselina-[(R)-4-(1-metil-2-okso-1,2,3,4-tetrahidro-kinolin-6-il)-5,6,7,8-tetrahidro-izokinolin-8-il]-amid;
N-[(R)-4-(1-metil-2-okso-1,2,3,4-tetrahidro-kinolin-6-il)-5,6,7,8-tetrahidro-izokinolin-8-il]-acetamid;
ciklopropankarboksilna kiselina-[(R)-4-(1-metil-2-okso-1,2,3,4-tetrahidro-kinolin-6-il)-5,6,7,8-tetrahidro-izokinolin-8-il]-amid;
N-[(R)-4-(1-metil-2-okso-1,2,3,4-tetrahidro-kinolin-6-il)-5,6,7,8-tetrahidro-izokinolin-8-il]-metansulfonamid;
ciklopropansulfonska kiselina-[(R)-4-(1-metil-2-okso-1,2,3,4-tetrahidro-kinolin-6-il)-5,6,7,8-tetrahidro-izokinolin-8-il]-amid;
(rac)-6-(8-hidroksi-5,6,7,8-tetrahidro-izokinolin-4-il)-1-metil-3,4-dihidrokinolin-2(1H)-on;
(S ili R)-6-(8-hidroksi-5,6,7,8-tetrahidro-izokinolin-4-il)-1-metil-3,4-dihidrokinolin-2(1H)-on;
(R ili S)-6-(8-hidroksi-5,6,7,8-tetrahidro-izokinolin-4-il)-1-metil-3,4-dihidrokinolin-2(1H)-on;
1-metil-6-(8-okso-5,6,7,8-tetrahidro-izokinolin-4-il)-3,4-dihidro-1H-kinolin-2-on;
N-[4-(1-metil-2-okso-1,2,3,4-tetrahidro-kinolin-6-il)-5,6-dihidro-izokinolin-8-il]-propionamid;
(+)-(R)-N-(4-(1-metil-2-okso-1,2,3,4-tetrahidrokinolin-6-il)-5,6,7,8-tetrahidroizokinolin-8-il)propionamid;
i njihove farmaceutski prihvatljive soli.
11. Spoj prema bilo kojem od zahtjeva 1 do 9, naznačen time, da je odabran iz skupine koju čine:
(+)-N-(4-(1-metil-2-okso-1,2,3,4-tetrahidrokinolin-6-il)-5,6,7,8-tetrahidroizokinolin-8-il)propionamid;
(+)-N-(4-(1-metil-2-okso-1,2,3,4-tetrahidrokinolin-6-il)-5,6,7,8-tetrahidroizokinolin-8-il)etansulfonamid;
(+)-N-(4-(1-metil-2-okso-1,2,3,4-tetrahidrokinolin-6-il)-6,7-dihidro-5H-ciklopenta[c]piridin-7-il)propionamid;
(rac)-N-(4-(1-metil-2-okso-1,2,3,4-tetrahidrokinolin-6-il)-6,7-dihidro-5H-ciklopenta[c]piridin-7-il)etansulfonamid;
N-{2-[5-(1-metil-2-okso-1,2,3,4-tetrahidro-kinolin-6-il)-3,4-dihidro-2H-[1,7]naftiridin-1-il]-etil}-propionamid;
i njihove farmaceutski prihvatljive soli.
12. Spoj prema bilo kojem od zahtjeva 1 do 8 i 10, naznačen time, da je odabran iz skupine koju čine:
(+)-(R ili S)-N-(4-(7-fluoro-1-metil-2-okso-1,2,3,4-tetrahidrokinolin-6-il)-6,7-dihidro-5H-ciklopenta[c]piridin-7-il)propionamid;
(+)-(R ili S)-N-(4-(7-fluoro-1-metil-2-okso-1,2,3,4-tetrahidrokinolin-6-il)-6,7-dihidro-5H-ciklopenta[c]piridin-7-il)etansulfonamid;
(+)-(R ili S)-N-[4-(7-fluoro-1-metil-2-okso-1,2,3,4-tetrahidro-kinolin-6-il)-5,6,7,8-tetrahidro-izokinolin-8-il]-propionamid;
(+)-N-[(R ili S)-4-(8-kloro-1-metil-2-okso-1,2,3,4-tetrahidro-kinolin-6-il)-5,6,7,8-tetrahidro-izokinolin-8-il]-propionamid;
(+)-N-[(7S,8R ili 7R,8S)-7-metil-4-(1-metil-2-okso-1,2,3,4-tetrahidro-kinolin-6-il)-5,6,7,8-tetrahidro-izokinolin-8-il]-propionamid;
(+)-N-[(7R,8R ili 7S,8S)-4-(7-fluoro-1-metil-2-okso-1,2,3,4-tetrahidro-kinolin-6-il)-7-metil-5,6,7,8-tetrahidro-izokinolin-8-il]-propionamid;
i njihove farmaceutski prihvatljive soli.
13. Spoj prema bilo kojem od patentnih zahtjeva 1 do 12, naznačen time, da je spoj (+)-(S ili R)-N-(4-(1-metil-2-okso-1,2,3,4-tetrahidrokinolin-6-il)-5,6,7,8-tetrahidroizokinolin-8-il)propionamid ili njegove farmaceutski prihvatljive soli.
14. Spoj prema bilo kojem od patentnih zahtjeva 1 do 8, 10 i 12, naznačen time, da je spoj (+)-(R)-N-(4-(1-metil-2-okso-1,2,3,4-tetrahidrokinolin-6-il)-5,6,7,8-tetrahidroizokinolin-8-il)propionamid ili njegove farmaceutski prihvatljive soli.
15. Spoj prema bilo kojem od patentnih zahtjeva 1 do 14, naznačen time, da se upotrebljava kao terapeutski aktivna tvar.
16. Spoj za uporabu prema patentnom zahtjevu 15, naznačen time, da je navedeni spoj (+)-(R)-N-(4-(1-metil-2-okso-1,2,3,4-tetrahidrokinolin-6-il)-5,6,7,8-tetrahidroizokinolin-8-il)propionamid ili njegove farmaceutski prihvatljive soli.
17. Farmaceutski pripravak, naznačen time, da sadrži spoj prema bilo kojem od zahtjeva 1 do 14 i terapeutski inertni nosač.
18. Farmaceutski pripravak prema patentnom zahtjevu 17, naznačen time, da je navedeni spoj (+)-(R)-N-(4-(1-metil-2-okso-1,2,3,4-tetrahidrokinolin-6-il)-5,6,7,8-tetrahidroizokinolin-8-il)propionamid ili njegove farmaceutski prihvatljive soli.
19. Spoj prema bilo kojem od patentnih zahtjeva 1 do 14, naznačen time, da se upotrebljava kod liječenja ili profilakse kronične bubrežne bolesti, kongestivnog zatajenja srca, visokog krvnog tlaka, primarnog aldosteronizma i Cushingovog sindroma .
20. Spoj za uporabu prema patentnom zahtjevu 19, naznačen time, da je navedeni spoj (+)-(R)-N-(4-(1-metil-2-okso-1,2,3,4-tetrahidrokinolin-6-il)-5,6,7,8-tetrahidroizokinolin-8-il)propionamid ili njegove farmaceutski prihvatljive soli.
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| CA2861060A1 (en) * | 2012-04-17 | 2013-10-24 | F. Hoffmann-La Roche Ag | New phenyl-tetrahydroisoquinoline derivatives |
| ES2646916T3 (es) | 2012-11-19 | 2017-12-18 | Bayer Pharma Aktiengesellschaft | Aminoimidazopiridazinas como inhibidores de MKNK1 cinasa |
| WO2014139981A1 (en) * | 2013-03-14 | 2014-09-18 | F. Hoffmann-La Roche Ag | Dihydroquinoline-2-one derivatives for use as aldosterone synthase inhibitors |
| RU2689421C2 (ru) * | 2013-05-27 | 2019-05-28 | Ф.Хоффманн-Ля Рош Аг | Новые 3,4-дигидро-2н-изохинолин-1-оны и 2,3-дигидро-изоиндол-1-оны |
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| US4792561A (en) * | 1986-05-29 | 1988-12-20 | Syntex (U.S.A.) Inc. | Carbostyril derivatives as combined thromboxane synthetase and cyclic-AMP phosphodiesterase inhibitors |
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| WO2005065050A2 (ja) * | 2003-12-25 | 2005-07-21 | Asahi Kasei Pharma Corporation | ２環化合物 |
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| DE102008022221A1 (de) | 2008-05-06 | 2009-11-12 | Universität des Saarlandes | Inhibitoren der humanen Aldosteronsynthase CYP11B2 |
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