HRP20210395T1 - Derivat 5-metil-6-fenil-4,5-dihidro-2h-piridazin-3-ona namijenjen liječenju tumora na mozgu - Google Patents
Derivat 5-metil-6-fenil-4,5-dihidro-2h-piridazin-3-ona namijenjen liječenju tumora na mozgu Download PDFInfo
- Publication number
- HRP20210395T1 HRP20210395T1 HRP20210395TT HRP20210395T HRP20210395T1 HR P20210395 T1 HRP20210395 T1 HR P20210395T1 HR P20210395T T HRP20210395T T HR P20210395TT HR P20210395 T HRP20210395 T HR P20210395T HR P20210395 T1 HRP20210395 T1 HR P20210395T1
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- Croatia
- Prior art keywords
- dihydro
- methyl
- pyridazin
- chloro
- phenyl
- Prior art date
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- GVASAZMJZKWWEA-UHFFFAOYSA-N 4-methyl-3-phenyl-4,5-dihydro-1h-pyridazin-6-one Chemical class CC1CC(=O)NN=C1C1=CC=CC=C1 GVASAZMJZKWWEA-UHFFFAOYSA-N 0.000 title 1
- 208000003174 Brain Neoplasms Diseases 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims 12
- 125000001424 substituent group Chemical group 0.000 claims 12
- 125000004450 alkenylene group Chemical group 0.000 claims 10
- 125000002947 alkylene group Chemical group 0.000 claims 10
- 150000003839 salts Chemical class 0.000 claims 10
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 7
- 150000001721 carbon Chemical group 0.000 claims 7
- 229910052799 carbon Inorganic materials 0.000 claims 7
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 6
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 4
- 229910052736 halogen Inorganic materials 0.000 claims 4
- 150000002367 halogens Chemical class 0.000 claims 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 3
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims 2
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims 2
- 125000004432 carbon atom Chemical group C* 0.000 claims 2
- 125000003161 (C1-C6) alkylene group Chemical group 0.000 claims 1
- 125000006590 (C2-C6) alkenylene group Chemical group 0.000 claims 1
- KSDZUQOHZPEGAW-UHFFFAOYSA-N BrC=1C(=C(C=CC=1OCC(C)(C)O)C=1C(CC(NN=1)=O)C)F Chemical compound BrC=1C(=C(C=CC=1OCC(C)(C)O)C=1C(CC(NN=1)=O)C)F KSDZUQOHZPEGAW-UHFFFAOYSA-N 0.000 claims 1
- MZRDLTPXVAVWOD-UHFFFAOYSA-N BrC=1C(=C(C=CC=1OCC(C)O)C=1C(CC(NN=1)=O)C)F Chemical compound BrC=1C(=C(C=CC=1OCC(C)O)C=1C(CC(NN=1)=O)C)F MZRDLTPXVAVWOD-UHFFFAOYSA-N 0.000 claims 1
- PYWIZXUMLFSZEX-UHFFFAOYSA-N BrC=1C(=C(C=CC=1OCC(CO)(F)F)C=1C(CC(NN=1)=O)C)F Chemical compound BrC=1C(=C(C=CC=1OCC(CO)(F)F)C=1C(CC(NN=1)=O)C)F PYWIZXUMLFSZEX-UHFFFAOYSA-N 0.000 claims 1
- ASFGCFVEXYLIDS-UHFFFAOYSA-N BrC=1C(=C(C=CC=1OCC1(CC1)O)C=1C(CC(NN=1)=O)C)F Chemical compound BrC=1C(=C(C=CC=1OCC1(CC1)O)C=1C(CC(NN=1)=O)C)F ASFGCFVEXYLIDS-UHFFFAOYSA-N 0.000 claims 1
- LNLQEROGDXEFAY-UHFFFAOYSA-N BrC=1C(=C(C=CC=1OCCCO)C=1C(CC(NN=1)=O)C)F Chemical compound BrC=1C(=C(C=CC=1OCCCO)C=1C(CC(NN=1)=O)C)F LNLQEROGDXEFAY-UHFFFAOYSA-N 0.000 claims 1
- SQTCBLVRSYMNNF-UHFFFAOYSA-N BrC=1C=C(C=C(C=1OCC(C)(C)O)Cl)C=1C(CC(NN=1)=O)C Chemical compound BrC=1C=C(C=C(C=1OCC(C)(C)O)Cl)C=1C(CC(NN=1)=O)C SQTCBLVRSYMNNF-UHFFFAOYSA-N 0.000 claims 1
- PWKFHUPPXIZQEQ-UHFFFAOYSA-N BrC=1C=C(C=C(C=1OCC(C)(C)O)F)C=1C(CC(NN=1)=O)C Chemical compound BrC=1C=C(C=C(C=1OCC(C)(C)O)F)C=1C(CC(NN=1)=O)C PWKFHUPPXIZQEQ-UHFFFAOYSA-N 0.000 claims 1
- SYZIAVRAWCTBKV-UHFFFAOYSA-N BrC=1C=C(C=C(C=1OCC(C)O)Cl)C=1C(CC(NN=1)=O)C Chemical compound BrC=1C=C(C=C(C=1OCC(C)O)Cl)C=1C(CC(NN=1)=O)C SYZIAVRAWCTBKV-UHFFFAOYSA-N 0.000 claims 1
- WANVZSRMIBKWLE-UHFFFAOYSA-N BrC=1C=C(C=C(C=1OCC(CO)(C)C)F)C=1C(CC(NN=1)=O)C Chemical compound BrC=1C=C(C=C(C=1OCC(CO)(C)C)F)C=1C(CC(NN=1)=O)C WANVZSRMIBKWLE-UHFFFAOYSA-N 0.000 claims 1
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims 1
- QZZVJMCJLBZRPH-UHFFFAOYSA-N ClC=1C(=C(C=C(C=1OCC(C)(C)O)C)C=1C(CC(NN=1)=O)C)F Chemical compound ClC=1C(=C(C=C(C=1OCC(C)(C)O)C)C=1C(CC(NN=1)=O)C)F QZZVJMCJLBZRPH-UHFFFAOYSA-N 0.000 claims 1
- LXYVJGSKSZCQLZ-UHFFFAOYSA-N ClC=1C(=C(C=C(C=1OCC(C)(C)O)F)C=1C(CC(NN=1)=O)C)F Chemical compound ClC=1C(=C(C=C(C=1OCC(C)(C)O)F)C=1C(CC(NN=1)=O)C)F LXYVJGSKSZCQLZ-UHFFFAOYSA-N 0.000 claims 1
- YZFXENGEYMVXSI-UHFFFAOYSA-N ClC=1C(=C(C=C(C=1OCC(C)O)C)C=1C(CC(NN=1)=O)C)F Chemical compound ClC=1C(=C(C=C(C=1OCC(C)O)C)C=1C(CC(NN=1)=O)C)F YZFXENGEYMVXSI-UHFFFAOYSA-N 0.000 claims 1
- HHIWLXCPLBXJOL-UHFFFAOYSA-N ClC=1C(=C(C=C(C=1OCC(CO)(C)C)C)C=1C(CC(NN=1)=O)C)F Chemical compound ClC=1C(=C(C=C(C=1OCC(CO)(C)C)C)C=1C(CC(NN=1)=O)C)F HHIWLXCPLBXJOL-UHFFFAOYSA-N 0.000 claims 1
- DOUKCVHHKVESMW-UHFFFAOYSA-N ClC=1C(=C(C=C(C=1OCC(CO)(F)F)C)C=1C(CC(NN=1)=O)C)F Chemical compound ClC=1C(=C(C=C(C=1OCC(CO)(F)F)C)C=1C(CC(NN=1)=O)C)F DOUKCVHHKVESMW-UHFFFAOYSA-N 0.000 claims 1
- GSWDFQVFHQHSEO-UHFFFAOYSA-N ClC=1C(=C(C=C(C=1OCC1(CC1)O)C)C=1C(CC(NN=1)=O)C)F Chemical compound ClC=1C(=C(C=C(C=1OCC1(CC1)O)C)C=1C(CC(NN=1)=O)C)F GSWDFQVFHQHSEO-UHFFFAOYSA-N 0.000 claims 1
- GANFERLGHHBMKO-UHFFFAOYSA-N ClC=1C(=C(C=C(C=1OCCCO)C)C=1C(CC(NN=1)=O)C)F Chemical compound ClC=1C(=C(C=C(C=1OCCCO)C)C=1C(CC(NN=1)=O)C)F GANFERLGHHBMKO-UHFFFAOYSA-N 0.000 claims 1
- KZSGHHOXCHTYKR-UHFFFAOYSA-N ClC=1C(=C(C=C(C=1OCCCO)F)C=1C(CC(NN=1)=O)C)F Chemical compound ClC=1C(=C(C=C(C=1OCCCO)F)C=1C(CC(NN=1)=O)C)F KZSGHHOXCHTYKR-UHFFFAOYSA-N 0.000 claims 1
- OVYUNHGOLHWCFD-ARJAWSKDSA-N ClC=1C(=C(C=C(C=1OC\C=C/CO)C)C=1C(CC(NN=1)=O)C)F Chemical compound ClC=1C(=C(C=C(C=1OC\C=C/CO)C)C=1C(CC(NN=1)=O)C)F OVYUNHGOLHWCFD-ARJAWSKDSA-N 0.000 claims 1
- JBXPZZTYPLSPJF-MRVPVSSYSA-N ClC=1C(=C(C=CC=1OCC(C)(C)O)C=1[C@@H](CC(NN=1)=O)C)F Chemical compound ClC=1C(=C(C=CC=1OCC(C)(C)O)C=1[C@@H](CC(NN=1)=O)C)F JBXPZZTYPLSPJF-MRVPVSSYSA-N 0.000 claims 1
- IQOFGKFNFVFMQB-UHFFFAOYSA-N ClC=1C(=C(C=CC=1OCC(C)O)C=1C(CC(NN=1)=O)C)F Chemical compound ClC=1C(=C(C=CC=1OCC(C)O)C=1C(CC(NN=1)=O)C)F IQOFGKFNFVFMQB-UHFFFAOYSA-N 0.000 claims 1
- QVHQAMIEXKICTK-UHFFFAOYSA-N ClC=1C(=C(C=CC=1OCC(CC)O)C=1C(CC(NN=1)=O)C)F Chemical compound ClC=1C(=C(C=CC=1OCC(CC)O)C=1C(CC(NN=1)=O)C)F QVHQAMIEXKICTK-UHFFFAOYSA-N 0.000 claims 1
- VYEQLKUZFUDBGQ-UHFFFAOYSA-N ClC=1C(=C(C=CC=1OCC1(CC1)O)C=1C(CC(NN=1)=O)C)F Chemical compound ClC=1C(=C(C=CC=1OCC1(CC1)O)C=1C(CC(NN=1)=O)C)F VYEQLKUZFUDBGQ-UHFFFAOYSA-N 0.000 claims 1
- YWWRBXHYFRHYED-UHFFFAOYSA-N ClC=1C(=C(C=CC=1OCCCO)C=1C(CC(NN=1)=O)C)F Chemical compound ClC=1C(=C(C=CC=1OCCCO)C=1C(CC(NN=1)=O)C)F YWWRBXHYFRHYED-UHFFFAOYSA-N 0.000 claims 1
- YFNPOYJPIJXSGF-UHFFFAOYSA-N ClC=1C=C(C=C(C=1OCC(C)(C)O)C)C=1C(CC(NN=1)=O)C Chemical compound ClC=1C=C(C=C(C=1OCC(C)(C)O)C)C=1C(CC(NN=1)=O)C YFNPOYJPIJXSGF-UHFFFAOYSA-N 0.000 claims 1
- YOBUWROPXQHLIN-UHFFFAOYSA-N ClC=1C=C(C=C(C=1OCC(C)(C)O)Cl)C=1C(CC(NN=1)=O)C Chemical compound ClC=1C=C(C=C(C=1OCC(C)(C)O)Cl)C=1C(CC(NN=1)=O)C YOBUWROPXQHLIN-UHFFFAOYSA-N 0.000 claims 1
- QGPLRCDNASAOCO-UHFFFAOYSA-N ClC=1C=C(C=C(C=1OCC(C)O)C)C=1C(CC(NN=1)=O)C Chemical compound ClC=1C=C(C=C(C=1OCC(C)O)C)C=1C(CC(NN=1)=O)C QGPLRCDNASAOCO-UHFFFAOYSA-N 0.000 claims 1
- GPMRWLQHSCNUED-UHFFFAOYSA-N ClC=1C=C(C=C(C=1OCC(C)O)Cl)C=1C(CC(NN=1)=O)C Chemical compound ClC=1C=C(C=C(C=1OCC(C)O)Cl)C=1C(CC(NN=1)=O)C GPMRWLQHSCNUED-UHFFFAOYSA-N 0.000 claims 1
- PFZFMICGPQBVHU-UHFFFAOYSA-N ClC=1C=C(C=C(C=1OCC(CCO)(C)C)Cl)C=1C(CC(NN=1)=O)C Chemical compound ClC=1C=C(C=C(C=1OCC(CCO)(C)C)Cl)C=1C(CC(NN=1)=O)C PFZFMICGPQBVHU-UHFFFAOYSA-N 0.000 claims 1
- KZNVKPRIZXOXJL-UHFFFAOYSA-N ClC=1C=C(C=C(C=1OCC(CCO)(C)C)F)C=1C(CC(NN=1)=O)C Chemical compound ClC=1C=C(C=C(C=1OCC(CCO)(C)C)F)C=1C(CC(NN=1)=O)C KZNVKPRIZXOXJL-UHFFFAOYSA-N 0.000 claims 1
- WDUVYHFOBZXXFC-UHFFFAOYSA-N ClC=1C=C(C=C(C=1OCC(CO)(C)C)C)C=1C(CC(NN=1)=O)C Chemical compound ClC=1C=C(C=C(C=1OCC(CO)(C)C)C)C=1C(CC(NN=1)=O)C WDUVYHFOBZXXFC-UHFFFAOYSA-N 0.000 claims 1
- ZRAHCUYWWFNMES-UHFFFAOYSA-N ClC=1C=C(C=C(C=1OCC(CO)(C)C)F)C=1C(CC(NN=1)=O)C Chemical compound ClC=1C=C(C=C(C=1OCC(CO)(C)C)F)C=1C(CC(NN=1)=O)C ZRAHCUYWWFNMES-UHFFFAOYSA-N 0.000 claims 1
- FLWRTLIIBAIWEO-UHFFFAOYSA-N ClC=1C=C(C=C(C=1OCC(CO)(F)F)C)C=1C(CC(NN=1)=O)C Chemical compound ClC=1C=C(C=C(C=1OCC(CO)(F)F)C)C=1C(CC(NN=1)=O)C FLWRTLIIBAIWEO-UHFFFAOYSA-N 0.000 claims 1
- NYGDWDCCDMLMLJ-UHFFFAOYSA-N ClC=1C=C(C=C(C=1OCC(CO)(F)F)Cl)C=1C(CC(NN=1)=O)C Chemical compound ClC=1C=C(C=C(C=1OCC(CO)(F)F)Cl)C=1C(CC(NN=1)=O)C NYGDWDCCDMLMLJ-UHFFFAOYSA-N 0.000 claims 1
- NKLDQNWQRYXXEI-UHFFFAOYSA-N ClC=1C=C(C=C(C=1OCC(CO)C)C)C=1C(CC(NN=1)=O)C Chemical compound ClC=1C=C(C=C(C=1OCC(CO)C)C)C=1C(CC(NN=1)=O)C NKLDQNWQRYXXEI-UHFFFAOYSA-N 0.000 claims 1
- WFWOZNWZFYFEKL-UHFFFAOYSA-N ClC=1C=C(C=C(C=1OCC1(CC1)O)C)C=1C(CC(NN=1)=O)C Chemical compound ClC=1C=C(C=C(C=1OCC1(CC1)O)C)C=1C(CC(NN=1)=O)C WFWOZNWZFYFEKL-UHFFFAOYSA-N 0.000 claims 1
- CFVDLKKAPNQOMA-UHFFFAOYSA-N ClC=1C=C(C=C(C=1OCC1(CC1)O)Cl)C=1C(CC(NN=1)=O)C Chemical compound ClC=1C=C(C=C(C=1OCC1(CC1)O)Cl)C=1C(CC(NN=1)=O)C CFVDLKKAPNQOMA-UHFFFAOYSA-N 0.000 claims 1
- QGPLRCDNASAOCO-LHIURRSHSA-N ClC=1C=C(C=C(C=1OC[C@@H](C)O)C)C=1C(CC(NN=1)=O)C Chemical compound ClC=1C=C(C=C(C=1OC[C@@H](C)O)C)C=1C(CC(NN=1)=O)C QGPLRCDNASAOCO-LHIURRSHSA-N 0.000 claims 1
- NLQXMSMLTOWMDU-UHFFFAOYSA-N FC(COC1=C(C(=C(C=C1C)C=1C(CC(NN=1)=O)C)F)C)(CO)F Chemical compound FC(COC1=C(C(=C(C=C1C)C=1C(CC(NN=1)=O)C)F)C)(CO)F NLQXMSMLTOWMDU-UHFFFAOYSA-N 0.000 claims 1
- ZMRXPAVQDGXSKL-UHFFFAOYSA-N FC1=C(C=CC(=C1C(F)(F)F)OCC(C)(C)O)C=1C(CC(NN=1)=O)C Chemical compound FC1=C(C=CC(=C1C(F)(F)F)OCC(C)(C)O)C=1C(CC(NN=1)=O)C ZMRXPAVQDGXSKL-UHFFFAOYSA-N 0.000 claims 1
- BOYWHXBOMLLJRU-UHFFFAOYSA-N FC1=C(C=CC(=C1C=C)OCC(C)O)C=1C(CC(NN=1)=O)C Chemical compound FC1=C(C=CC(=C1C=C)OCC(C)O)C=1C(CC(NN=1)=O)C BOYWHXBOMLLJRU-UHFFFAOYSA-N 0.000 claims 1
- GGUTYKLJESECBW-MRVPVSSYSA-N FC1=C(C=CC(=C1F)OCC(C)(C)O)C=1[C@@H](CC(NN=1)=O)C Chemical compound FC1=C(C=CC(=C1F)OCC(C)(C)O)C=1[C@@H](CC(NN=1)=O)C GGUTYKLJESECBW-MRVPVSSYSA-N 0.000 claims 1
- 125000003342 alkenyl group Chemical group 0.000 claims 1
- 125000003545 alkoxy group Chemical group 0.000 claims 1
- 201000011510 cancer Diseases 0.000 claims 1
- 229910052801 chlorine Inorganic materials 0.000 claims 1
- 125000001309 chloro group Chemical group Cl* 0.000 claims 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims 1
- 229910052731 fluorine Inorganic materials 0.000 claims 1
- 125000001153 fluoro group Chemical group F* 0.000 claims 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D237/00—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings
- C07D237/02—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings not condensed with other rings
- C07D237/04—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings not condensed with other rings having less than three double bonds between ring members or between ring members and non-ring members
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D237/00—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings
- C07D237/02—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings not condensed with other 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
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- A61K31/50—Pyridazines; Hydrogenated pyridazines
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D237/00—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings
- C07D237/02—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings not condensed with other rings
- C07D237/06—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
- C07D237/10—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members 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
- C07D237/14—Oxygen atoms
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Public Health (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Epidemiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Pyridine Compounds (AREA)
Claims (10)
1. Spoj formule (1):
[image]
,
ili njegova farmaceutski prihvatljiva sol, naznačen time što:
R1 do R4 su neovisno atom vodika, halogen, OH, CN, C1-6 alkilna skupina, halogenirana C1-6 alkilna skupina, C2-6 alkenilna skupina, C1-6 alkoksi skupina ili halogenirana C1-6 alkoksi skupina, uz uvjet da su jedan ili dva od R1 do R4 atomi vodika, no svi od tri ili četiri njih ne mogi biti atomi vodika; i
Y je C1-6 alkilen ili C2-6 alkenilenska skupina, gdje alkilenska ili alkenilenska skupina može biti supstituirana s jednim ili više supstituenata koje se neovisno bira iz skupine koju čine C1-6 alkilna skupina, halogen, te halogenirana C1-6 alkilna skupina, nadalje gdje se atom ugljika koji može biti supstituiran u supstituentu koji se veže na alkilensku ili alkenilensku skupinu i drugi atom ugljika koji može biti supstituiran u alkilenskoj ili alkenilenskoj skupini, ili dva atoma ugljika koji mogu nositi supstituent(e) u supstituentu koji se veže na alkilensku ili alkenilensku skupinu može kombinirati zajedno kako bi tvorili 3- do 6-eročlani ugljični prsten.
2. Spoj u skladu s patentnim zahtjevom 1, ili njegova farmaceutski prihvatljiva sol, naznačen time što su bilo koja dva od R1 do R4 atomi vodika.
3. Spoj u skladu s patentnim zahtjevom 1 ili 2, ili njegova farmaceutski prihvatljiva sol, naznačen time što su R1 do R4 neovisno atom vodika, halogen, OH, CN, C1-4 alkilna skupina, halogenirana C1-4 alkilna skupina, C2-4 alkenilna skupina, C1-4 alkoksi skupina, ili halogenirani C1-4 alkoksi skupina.
4. Spoj u skladu s patentnim zahtjevom 1 ili 2, ili njegova farmaceutski prihvatljiva sol, naznačen time što su R1 do R4 neovisno atom vodika, atom fluora, atom klora, OH, CN, C1-4 alkilna skupina, vinilna skupina ili C1-4 alkoksi skupina.
5. Spoj u skladu s bilo kojim od patentnih zahtjeva 1 do 4, ili njegova farmaceutski prihvatljiva sol, naznačen time što je alkilenska ili alkenilenska skupina u Y supstituirana s jednim ili više supstituenata koje se neovisno bira iz skupine koju čine C1-4 alkilna skupina, halogen, te halogenirana C1-4 alkilna skupina, nadalje gdje se atom ugljika koji može biti supstituiran u supstituentu koji se veže na alkilensku ili alkenilensku skupinu i drugi atom ugljika koji može biti supstituiran u alkilenskoj ili alkenilenskoj skupini, ili dva atoma ugljika koji mogu nositi supstituent(e) u supstituentu koji se veže na alkilensku ili alkenilensku skupinu može kombinirati zajedno kako bi tvorili 3- do 6-eročlani ugljični prsten.
6. Spoj u skladu s bilo kojim od patentnih zahtjeva 1 do 4, ili njegova farmaceutski prihvatljiva sol, naznačen time što je atom ugljika u alkilenskoj ili alkenilenskoj skupini u Y supstituiran s jednim ili dva supstituenta koje se neovisno bira iz skupine koju čine C1-4 alkilna skupina i halogenirana C1-4 alkilna skupina, nadalje kada je atom ugljika supstituiran s dva supstituenta, gdje se svaki atom ugljika koji može biti supstituiran u dva supstituenta može kombinirati zajedno kako bi tvorili 3- do 6-eročlani ugljični prsten.
7. Spoj u skladu s bilo kojim od patentnih zahtjeva 1 do 4, ili njegova farmaceutski prihvatljiva sol, naznačen time što alkilenska ili alkenilenska skupina u Y nema supstituent.
8. Spoj u skladu s bilo kojim od patentnih zahtjeva 1 do 7, ili njegova farmaceutski prihvatljiva sol, naznačen time što spoj formule (1) prikazuje sljedeća formula:
[image]
.
9. Spoj u skladu s patentnim zahtjevom 1, ili njegova farmaceutski prihvatljiva sol, naznačen time što ga se bira između sljedećih spojeva:
6-[3-brom-5-klor-4-(2-hidroksi-2-metilpropoksi)fenil]-5-metil-4,5-dihidro-2H-piridazin-3-ona,
6-[3,5-diklor-4-(2-hidroksi-2-metilpropoksi)fenil]-5-metil-4,5-dihidro-2H-piridazin-3-ona,
6-[3-klor-5-fluor-4-(3-hidroksi-2,2-dimetilpropoksi)fenil]-5-metil-4,5-dihidro-2H-piridazin-3-ona,
6-[3-brom-2-fluor-4-(3-hidroksipropoksi)fenil]-5-metil-4,5-dihidro-2H-piridazin-3-ona,
6-[3-klor-2-fluor-4-(3-hidroksipropoksi)fenil]-5-metil-4,5-dihidro-2H-piridazin-3-ona,
6-[3-klor-2-fluor-4-(3-hidroksipropoksi)-5-metilfenil]-5-metil-4,5-dihidro-2H-piridazin-3-ona,
6-[3-brom-2-fluor-4-(2-hidroksi-2-metilpropoksi)fenil]-5-metil-4,5-dihidro-2H-piridazin-3-ona,
6-[3-brom-5-fluor-4-(2-hidroksi-2-metilpropoksi)fenil]-5-metil-4,5-dihidro-2H-piridazin-3-ona,
6-[3-klor-4-(2-hidroksi-2-metilpropoksi)-5-metilfenil]-5-metil-4,5-dihidro-2H-piridazin-3-ona,
6-[3-klor-2-fluor-4-(2-hidroksi-2-metilpropoksi)-5-metilfenil]-5-metil-4,5-dihidro-2H-piridazin-3-ona,
6-{3-klor-4-[(2R)-2-hidroksipropoksi]-5-metilfenil}-5-metil-4,5-dihidro-2H-piridazin-3-ona,
6-{3-klor-4-[(1-hidroksiciklopropil)metoksi]-5-metilfenil}-5-metil-4,5-dihidro-2H-piridazin-3-ona,
6-{3-klor-2-fluor-4-[(1-hidroksiciklopropil)metoksi]fenil}-5-metil-4,5-dihidro-2H-piridazin-3-ona,
6-[3-brom-2-fluor-4-(2-hidroksipropoksi)fenil]-5-metil-4,5-dihidro-2H-piridazin-3-ona,
6-[3,5-diklor-4-(2-hidroksipropoksi)fenil]-5-metil-4,5-dihidro-2H-piridazin-3-ona,
6-[3-klor-2-fluor-4-(2-hidroksipropoksi)fenil]-5-metil-4,5-dihidro-2H-piridazin-3-ona,
6-[3-klor-4-(2-hidroksipropoksi)-5-metilfenil]-5-metil-4,5-dihidro-2H-piridazin-3-ona,
6-[3-brom-5-klor-4-(2-hidroksipropoksi)fenil]-5-metil-4,5-dihidro-2H-piridazin-3-ona,
6-[2-fluor-4-(2-hidroksipropoksi)-3-vinilfenil]-5-metil-4,5-dihidro-2H-piridazin-3-ona,
6-[3-klor-2-fluor-4-(2-hidroksibutoksi)fenil]-5-metil-4,5-dihidro-2H-piridazin-3-ona,
6-[3-brom-5-fluor-4-(3-hidroksi-2,2-dimetilpropoksi)fenil]-5-metil-4,5-dihidro-2H-piridazin-3-ona,
6-[3-klor-4-(3-hidroksi-2,2-dimetilpropoksi)-5-metilfenil]-5-metil-4,5-dihidro-2H-piridazin-3-ona,
6-[3-klor-5-fluor-4-(4-hidroksi-2,2-dimetilbutoksi)fenil]-5-metil-4,5-dihidro-2H-piridazin-3-ona,
6-[3,5-diklor-4-(4-hidroksi-2,2-dimetilbutoksi)fenil]-5-metil-4,5-dihidro-2H-piridazin-3-ona,
6-[3,5-diklor-4-(2,2-difluor-3-hidroksipropoksi)fenil]-5-metil-4,5-dihidro-2H-piridazin-3-ona,
6-[3-brom-4-(2,2-difluor-3-hidroksipropoksi)-2-fluorfenil]-5-metil-4,5-dihidro-2H-piridazin-3-ona,
6-[3-klor-4-(2,2-difluor-3-hidroksipropoksi)-5-metilfenil]-5-metil-4,5-dihidro-2H-piridazin-3-ona,
(5R)-(–)-6-[3-klor-2-fluor-4-(2-hidroksi-2-metilpropoksi)fenil]-5-metil-4,5-dihidro-2H-piridazin-3-ona,
(5R)-(–)-6-[4-(2,2-difluor-3-hidroksipropoksi)-2-fluor-3-metilfenil]-5-metil-4,5-dihidro-2H-piridazin-3-ona,
(5R)-(–)-6-[2,3-difluor-4-(2-hidroksi-2-metilpropoksi)fenil]-5-metil-4,5-dihidro-2H-piridazin-3-ona,
(5R)-(–)-6-[3-fluor-4-(3-hidroksi-2,2-dimetilpropoksi)-5-metilfenil]-5-metil-4,5-dihidro-2H-piridazin-3-ona,
(5R)-(–)-6-[3-brom-5-klor-4-(3-hidroksi-2,2-dimetilpropoksi)fenil]-5-metil-4,5-dihidro-2H-piridazin-3-ona,
6-[3-klor-2,5-difluor-4-(2-hidroksi-2-metilpropoksi)fenil]-5-metil-4,5-dihidro-2H-piridazin-3-ona,
6-[3-klor-2-fluor-4-(3-hidroksi-2,2-dimetilpropoksi)-5-metilfenil]-5-metil-4,5-dihidro-2H-piridazin-3-ona,
6-[3-klor-2,5-difluor-4-(3-hidroksipropoksi)fenil]-5-metil-4,5-dihidro-2H-piridazin-3-ona,
6-[3-klor-4-(3-hidroksi-2-metilpropoksi)-5-metilfenil]-5-metil-4,5-dihidro-2H-piridazin-3-ona,
6-[3-klor-2-fluor-4-(2-hidroksipropoksi)-5-metilfenil]-5-metil-4,5-dihidro-2H-piridazin-3-ona,
6-{3-klor-2-fluor-4-[(Z)-4-hidroksi-2-buteniloksi]-5-metilfenil}-5-metil-4,5-dihidro-2H-piridazin-3-ona,
6-(3-klor-4-{[(1S*,2R*)-2-(hidroksimetil)ciklopropil]metoksi}-5-metilfenil)-5-metil-4,5-dihidro-2H-piridazin-3-ona,
6-[3-klor-4-(2,2-difluor-3-hidroksipropoksi)-2-fluor-5-metilfenil]-5-metil-4,5-dihidro-2H-piridazin-3-ona,
6-[4-(2,2-difluor-3-hidroksipropoksi)-2-fluor-3,5-dimetilfenil]-5-metil-4,5-dihidro-2H-piridazin-3-ona,
6-{3-klor-2-fluor-4-[(1-hidroksiciklopropil)metoksi]-5-metilfenil}-5-metil-4,5-dihidro-2H-piridazin-3-ona,
6-{3-brom-2-fluor-4-[(1-hidroksiciklopropil)metoksi]fenil}-5-metil-4,5-dihidro-2H-piridazin-3-ona,
6-{3,5-diklor-4-[(1-hidroksiciklopropil)metoksi]fenil}-5-metil-4,5-dihidro-2H-piridazin-3-ona, te
6-[2-fluor-4-(2-hidroksi-2-metilpropoksi)-3-(trifluormetil)fenil]-5-metil-4,5-dihidro-2H-piridazin-3-ona.
10. Spoj u skladu s bilo kojim od patentnih zahtjeva 1 do 9, ili njegova farmaceutska sol, naznačen time što je namijenjen upotrebi u liječenju zloćudnog tumora.
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PCT/JP2017/008246 WO2017150654A1 (en) | 2016-03-04 | 2017-03-02 | 5-methyl-6-phenyl-4,5-dihydro-2h-pyridazin-3-one derivative |
EP17711366.9A EP3423440B9 (en) | 2016-03-04 | 2017-03-02 | 5-methyl-6-phenyl-4,5-dihydro-2h-pyridazin-3-one derivative for the treatment of brain tumors |
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CN113348165B (zh) * | 2019-02-01 | 2024-06-25 | 拜耳股份有限公司 | 用于治疗过度增殖性疾病的1,2,4-三嗪-3(2h)-酮化合物 |
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US5100892A (en) | 1990-11-13 | 1992-03-31 | Glaxo Inc. | Dihydropyridine vasodilator agents |
US5563143A (en) * | 1994-09-21 | 1996-10-08 | Pfizer Inc. | Catechol diether compounds as inhibitors of TNF release |
CN1136197C (zh) * | 1996-05-30 | 2004-01-28 | 霍夫曼-拉罗奇有限公司 | 新的哒嗪酮衍生物 |
CA2588949A1 (en) | 2004-11-30 | 2006-06-08 | Artesian Therapeutics, Inc. | Compounds with mixed pde-inhibitory and .beta.-adrenergic antagonist or partial agonist activity for treatment of heart failure |
US20100160335A1 (en) | 2007-06-19 | 2010-06-24 | Kyorin Pharmaceutical Co., Ltd. | Pyridazinone derivative and pde inhibitor containing the same as active ingredient |
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