HRP20110650T1 - DERIVATI 1,2,3,4-TETRAHIDROPIROLO[1,2-a]PIRAZIN-6-KARBOKSAMIDA I 2,3,4,5-TETRAHIDROPIROLO[1,2-a]DIAZEPIN-7-KARBOKSAMIDA, NJIHOVO DOBIVANJE I UPOTREBA U TERAPIJI - Google Patents
DERIVATI 1,2,3,4-TETRAHIDROPIROLO[1,2-a]PIRAZIN-6-KARBOKSAMIDA I 2,3,4,5-TETRAHIDROPIROLO[1,2-a]DIAZEPIN-7-KARBOKSAMIDA, NJIHOVO DOBIVANJE I UPOTREBA U TERAPIJI Download PDFInfo
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- HRP20110650T1 HRP20110650T1 HR20110650T HRP20110650T HRP20110650T1 HR P20110650 T1 HRP20110650 T1 HR P20110650T1 HR 20110650 T HR20110650 T HR 20110650T HR P20110650 T HRP20110650 T HR P20110650T HR P20110650 T1 HRP20110650 T1 HR P20110650T1
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- benzyl
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- CHVBEBZZBGCXQP-UHFFFAOYSA-N 1,2,3,4-tetrahydropyrrolo[1,2-a]pyrazine-6-carboxamide Chemical compound C1NCCN2C(C(=O)N)=CC=C21 CHVBEBZZBGCXQP-UHFFFAOYSA-N 0.000 title abstract 2
- 230000001225 therapeutic effect Effects 0.000 title abstract 2
- 229940053202 antiepileptics carboxamide derivative Drugs 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims 21
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 17
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 12
- 150000003839 salts Chemical class 0.000 claims 10
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims 9
- 239000002253 acid Substances 0.000 claims 9
- 208000024827 Alzheimer disease Diseases 0.000 claims 8
- 229910020008 S(O) Inorganic materials 0.000 claims 7
- 125000003118 aryl group Chemical group 0.000 claims 7
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims 7
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims 6
- 229910052736 halogen Inorganic materials 0.000 claims 6
- 125000005843 halogen group Chemical group 0.000 claims 6
- PBIUDEUWYGBHDW-UHFFFAOYSA-N 2-chloro-1-pyridin-3-ylethanone;hydrochloride Chemical compound Cl.ClCC(=O)C1=CC=CN=C1 PBIUDEUWYGBHDW-UHFFFAOYSA-N 0.000 claims 5
- 229940079593 drug Drugs 0.000 claims 5
- 239000003814 drug Substances 0.000 claims 5
- 150000002367 halogens Chemical class 0.000 claims 5
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 claims 4
- 201000006474 Brain Ischemia Diseases 0.000 claims 4
- 208000005145 Cerebral amyloid angiopathy Diseases 0.000 claims 4
- 206010067889 Dementia with Lewy bodies Diseases 0.000 claims 4
- 201000011240 Frontotemporal dementia Diseases 0.000 claims 4
- 201000002832 Lewy body dementia Diseases 0.000 claims 4
- 208000026139 Memory disease Diseases 0.000 claims 4
- 208000018737 Parkinson disease Diseases 0.000 claims 4
- 206010035226 Plasma cell myeloma Diseases 0.000 claims 4
- 206010039966 Senile dementia Diseases 0.000 claims 4
- 229910052799 carbon Inorganic materials 0.000 claims 4
- 230000002490 cerebral effect Effects 0.000 claims 4
- 208000010877 cognitive disease Diseases 0.000 claims 4
- 125000005842 heteroatom Chemical group 0.000 claims 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 4
- 229910052757 nitrogen Inorganic materials 0.000 claims 4
- 229910052760 oxygen Inorganic materials 0.000 claims 4
- 230000002265 prevention Effects 0.000 claims 4
- 208000022256 primary systemic amyloidosis Diseases 0.000 claims 4
- 201000010374 Down Syndrome Diseases 0.000 claims 3
- 206010044688 Trisomy 21 Diseases 0.000 claims 3
- 125000004093 cyano group Chemical group *C#N 0.000 claims 3
- 208000019901 Anxiety disease Diseases 0.000 claims 2
- 201000001320 Atherosclerosis Diseases 0.000 claims 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 2
- 208000020406 Creutzfeldt Jacob disease Diseases 0.000 claims 2
- 208000003407 Creutzfeldt-Jakob Syndrome Diseases 0.000 claims 2
- 208000010859 Creutzfeldt-Jakob disease Diseases 0.000 claims 2
- 208000032131 Diabetic Neuropathies Diseases 0.000 claims 2
- 208000023105 Huntington disease Diseases 0.000 claims 2
- 208000019695 Migraine disease Diseases 0.000 claims 2
- 208000019022 Mood disease Diseases 0.000 claims 2
- 206010028980 Neoplasm Diseases 0.000 claims 2
- 206010002026 amyotrophic lateral sclerosis Diseases 0.000 claims 2
- 230000036506 anxiety Effects 0.000 claims 2
- 125000003710 aryl alkyl group Chemical group 0.000 claims 2
- 208000035269 cancer or benign tumor Diseases 0.000 claims 2
- 150000001721 carbon Chemical group 0.000 claims 2
- 125000004432 carbon atom Chemical group C* 0.000 claims 2
- 125000006317 cyclopropyl amino group Chemical group 0.000 claims 2
- 206010027599 migraine Diseases 0.000 claims 2
- 201000006417 multiple sclerosis Diseases 0.000 claims 2
- 208000027232 peripheral nervous system disease Diseases 0.000 claims 2
- 208000033808 peripheral neuropathy Diseases 0.000 claims 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims 2
- 229920006395 saturated elastomer Polymers 0.000 claims 2
- 208000019553 vascular disease Diseases 0.000 claims 2
- 125000006727 (C1-C6) alkenyl group Chemical group 0.000 claims 1
- 125000003161 (C1-C6) alkylene group Chemical group 0.000 claims 1
- 125000006728 (C1-C6) alkynyl group Chemical group 0.000 claims 1
- WGHUZQFIBFGNMX-QCENPCRXSA-N 2-heptan-4-yl-n-[(2s,3r)-3-hydroxy-1-phenyl-4-[[1-[3-(trifluoromethyl)phenyl]cyclopropyl]amino]butan-2-yl]-1-oxo-3,4-dihydropyrrolo[1,2-a]pyrazine-6-carboxamide Chemical compound C([C@H](NC(=O)C=1N2CCN(C(C2=CC=1)=O)C(CCC)CCC)[C@H](O)CNC1(CC1)C=1C=C(C=CC=1)C(F)(F)F)C1=CC=CC=C1 WGHUZQFIBFGNMX-QCENPCRXSA-N 0.000 claims 1
- VJMDJPRHOYXIBO-BHBYDHKZSA-N 2-heptan-4-yl-n-[(2s,3r)-3-hydroxy-1-phenyl-4-[[3-(trifluoromethyl)phenyl]methylamino]butan-2-yl]-1-oxo-3,4-dihydropyrrolo[1,2-a]pyrazine-6-carboxamide Chemical compound C([C@H](NC(=O)C=1N2CCN(C(C2=CC=1)=O)C(CCC)CCC)[C@H](O)CNCC=1C=C(C=CC=1)C(F)(F)F)C1=CC=CC=C1 VJMDJPRHOYXIBO-BHBYDHKZSA-N 0.000 claims 1
- KJJLSXVCXMVPCW-QCENPCRXSA-N 2-heptan-4-yl-n-[(2s,3r)-3-hydroxy-1-phenyl-4-[[3-(trifluoromethyl)phenyl]methylamino]butan-2-yl]-1-oxo-4,5-dihydro-3h-pyrrolo[1,2-a][1,4]diazepine-7-carboxamide Chemical compound C([C@H](NC(=O)C=1N2CCCN(C(C2=CC=1)=O)C(CCC)CCC)[C@H](O)CNCC=1C=C(C=CC=1)C(F)(F)F)C1=CC=CC=C1 KJJLSXVCXMVPCW-QCENPCRXSA-N 0.000 claims 1
- IEDGYXJNHWQNIV-LITSAYRRSA-N 2-o-tert-butyl 8-o-methyl 6-[[(2s,3r)-3-hydroxy-1-phenyl-4-[[1-[3-(trifluoromethyl)phenyl]cyclopropyl]amino]butan-2-yl]carbamoyl]-3,4-dihydro-1h-pyrrolo[1,2-a]pyrazine-2,8-dicarboxylate Chemical compound C([C@H](NC(=O)C1=CC(=C2CN(CCN21)C(=O)OC(C)(C)C)C(=O)OC)[C@H](O)CNC1(CC1)C=1C=C(C=CC=1)C(F)(F)F)C1=CC=CC=C1 IEDGYXJNHWQNIV-LITSAYRRSA-N 0.000 claims 1
- VCAVVPVBICCMCM-RKGTXJDOSA-N 6-[[(2s,3r)-3-hydroxy-1-phenyl-4-[[1-[3-(trifluoromethyl)phenyl]cyclopropyl]amino]butan-2-yl]carbamoyl]-1,2,3,4-tetrahydropyrrolo[1,2-a]pyrazine-8-carboxylic acid;hydrochloride Chemical compound Cl.C([C@@H](O)[C@H](CC=1C=CC=CC=1)NC(=O)C=1N2CCNCC2=C(C(O)=O)C=1)NC1(C=2C=C(C=CC=2)C(F)(F)F)CC1 VCAVVPVBICCMCM-RKGTXJDOSA-N 0.000 claims 1
- HMAKBLUALSUNRB-LBNVMWSVSA-N 6-[[(2s,3r)-3-hydroxy-1-phenyl-4-[[1-[3-(trifluoromethyl)phenyl]cyclopropyl]amino]butan-2-yl]carbamoyl]-2-[(2-methylpropan-2-yl)oxycarbonyl]-3,4-dihydro-1h-pyrrolo[1,2-a]pyrazine-8-carboxylic acid Chemical class C([C@H](NC(=O)C1=CC(=C2N1CCN(C2)C(=O)OC(C)(C)C)C(O)=O)[C@H](O)CNC1(CC1)C=1C=C(C=CC=1)C(F)(F)F)C1=CC=CC=C1 HMAKBLUALSUNRB-LBNVMWSVSA-N 0.000 claims 1
- HNRFFYREWDVYJD-UHFFFAOYSA-N 8-methoxycarbonyl-2-[(2-methylpropan-2-yl)oxycarbonyl]-3,4-dihydro-1h-pyrrolo[1,2-a]pyrazine-6-carboxylic acid Chemical compound C1CN(C(=O)OC(C)(C)C)CC2=C(C(=O)OC)C=C(C(O)=O)N21 HNRFFYREWDVYJD-UHFFFAOYSA-N 0.000 claims 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims 1
- 125000003277 amino group Chemical group 0.000 claims 1
- 125000004429 atom Chemical group 0.000 claims 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 1
- 241001233037 catfish Species 0.000 claims 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims 1
- 201000010099 disease Diseases 0.000 claims 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 1
- -1 groups NR7R8 Chemical group 0.000 claims 1
- 229910052739 hydrogen Inorganic materials 0.000 claims 1
- 239000001257 hydrogen Substances 0.000 claims 1
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 1
- 229940126601 medicinal product Drugs 0.000 claims 1
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 claims 1
- 125000000896 monocarboxylic acid group Chemical group 0.000 claims 1
- UTVOVYBYZADRLJ-QCENPCRXSA-N n-[(2s,3r)-1-(3,5-difluorophenyl)-3-hydroxy-4-[[1-[3-(trifluoromethyl)phenyl]cyclopropyl]amino]butan-2-yl]-2-heptan-4-yl-1-oxo-3,4-dihydropyrrolo[1,2-a]pyrazine-6-carboxamide Chemical compound C([C@H](NC(=O)C=1N2CCN(C(C2=CC=1)=O)C(CCC)CCC)[C@H](O)CNC1(CC1)C=1C=C(C=CC=1)C(F)(F)F)C1=CC(F)=CC(F)=C1 UTVOVYBYZADRLJ-QCENPCRXSA-N 0.000 claims 1
- GGEZZXYGWMFPAS-LBNVMWSVSA-N n-[(2s,3r)-3-hydroxy-1-phenyl-4-[[3-(trifluoromethyl)phenyl]methylamino]butan-2-yl]-1-oxo-2-pentan-3-yl-3,4-dihydropyrrolo[1,2-a]pyrazine-6-carboxamide Chemical compound C([C@H](NC(=O)C=1N2CCN(C(C2=CC=1)=O)C(CC)CC)[C@H](O)CNCC=1C=C(C=CC=1)C(F)(F)F)C1=CC=CC=C1 GGEZZXYGWMFPAS-LBNVMWSVSA-N 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- 239000000825 pharmaceutical preparation Substances 0.000 claims 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 1
- 229910052717 sulfur Inorganic materials 0.000 claims 1
- 208000011580 syndromic disease Diseases 0.000 claims 1
- CAICDEXBTDQTHY-BHDXBOSCSA-N tert-butyl 8-(diethylcarbamoyl)-6-[[(2s,3r)-3-hydroxy-1-phenyl-4-[[1-[3-(trifluoromethyl)phenyl]cyclopropyl]amino]butan-2-yl]carbamoyl]-3,4-dihydro-1h-pyrrolo[1,2-a]pyrazine-2-carboxylate Chemical compound C([C@H](NC(=O)C1=CC(=C2CN(CCN21)C(=O)OC(C)(C)C)C(=O)N(CC)CC)[C@H](O)CNC1(CC1)C=1C=C(C=CC=1)C(F)(F)F)C1=CC=CC=C1 CAICDEXBTDQTHY-BHDXBOSCSA-N 0.000 claims 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 1
- UERAUKQJMDAHHP-UHFFFAOYSA-N 2,3,4,5-tetrahydro-1h-pyrrolo[1,2-a][1,4]diazepine-7-carboxamide Chemical class C1NCCCN2C(C(=O)N)=CC=C21 UERAUKQJMDAHHP-UHFFFAOYSA-N 0.000 abstract 1
Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D241/00—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings
- C07D241/02—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings
- C07D241/06—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings having one or two double bonds between ring members or between ring members and non-ring members
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/02—Drugs for disorders of the nervous system for peripheral neuropathies
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/06—Antimigraine agents
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/14—Drugs for disorders of the nervous system for treating abnormal movements, e.g. chorea, dyskinesia
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/14—Drugs for disorders of the nervous system for treating abnormal movements, e.g. chorea, dyskinesia
- A61P25/16—Anti-Parkinson drugs
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/22—Anxiolytics
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/24—Antidepressants
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
-
- 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
- A61P35/00—Antineoplastic agents
-
- 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
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/30—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members
- C07D207/34—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two 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
- C07D207/36—Oxygen or sulfur atoms
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D241/00—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings
- C07D241/02—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings
- C07D241/06—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings having one or two double bonds between ring members or between ring members and non-ring members
- C07D241/08—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings having one or two double bonds between ring members or between ring members and non-ring members with oxygen atoms directly attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D243/00—Heterocyclic compounds containing seven-membered rings having two nitrogen atoms as the only ring hetero atoms
- C07D243/06—Heterocyclic compounds containing seven-membered rings having two nitrogen atoms as the only ring hetero atoms having the nitrogen atoms in positions 1 and 4
- C07D243/08—Heterocyclic compounds containing seven-membered rings having two nitrogen atoms as the only ring hetero atoms having the nitrogen atoms in positions 1 and 4 not condensed with other rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Medicinal Chemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Diabetes (AREA)
- Psychology (AREA)
- Pain & Pain Management (AREA)
- Psychiatry (AREA)
- Emergency Medicine (AREA)
- Obesity (AREA)
- Urology & Nephrology (AREA)
- Hematology (AREA)
- Endocrinology (AREA)
- Hospice & Palliative Care (AREA)
- Vascular Medicine (AREA)
- Heart & Thoracic Surgery (AREA)
- Cardiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Abstract
Spoj prema formuli (I) naznačen time što: R1 predstavlja atom vodika, (C1-C10)alkilnu, (C3-C7)cikloalkilnu, (CH2)n-(C1-C6)alkenilnu, (CH2)n-(C1-C6)alkinilnu ili (C1-C6)alkil-Z-(C1-C6)alkilnu skupinu, gdje Z predstavlja heteroatom koji se bira između O, N i S(O)m, ili inače R1 predstavlja skupinu COOR, S(O)mR, arilnu ili aralkilnu skupinu; (C1-C10)alkilna, (C3-C7)cikloalkilna, (CH2)n-(C1-C6)alkenilna, (CH2)n-(C1-C6)alkinilna, (C1-C6)alkil-Z-(C1-C6)alkilna, arilna ili aralkilna skupina izborno su supstituirane s jednom ili više skupina koje se bira između atoma halogena, (C1-C6)alkilne, (C3-C7)cikloalkilne, halogen(C1-C6)alkilne, (C1-C6)alkoksi, halogen(C1-C6)alkoksi, skupine NR7R8, nitro, cijano skupine, skupine OR, COOR, C(O)NR7R8 ili S(O)mNR7R8; R2 predstavlja jednu ili više skupina koje se bira između atoma vodika, atoma halogena, (C1-C6)alkilne, (C3-C7)cikloalkilne, (C1-C6)alkenilne, (C1-C6)alkinilne ili (C1-C6)alkil-Z-(C1-C6)alkilne skupine, gdje Z predstavlja heteroatom koji se bira između O, N i S(O)m, ili inače R2 predstavlja halogen(C1-C6)alkilnu, halogen(C1-C6)alkoksi, hidroksi, (C1-C6)alkoksi, nitro, cijano ili amino skupinu, skupinu NR7R8, COOR, C(O)NR7R8, O-C(O)(C1-C6)alkilnu ili skupinu S(O)m-NR7R8 ili arilnu skupinu, gdje arilna skupina može biti izborno supstituirana s jednom ili više skupina koje se bira između atoma halogena, (C1-C6)alkilne, (C3-C7)cikloalkilne, halogen(C1-C6)alkilne, (C1-C6)alkoksi, halogen(C1-C6)alkoksi skupine, skupine NR7R8, OR, nitro, cijano skupine, skupine COOR, C(O)NR7R8 ili S(O)mNR7R8; R3 predstavlja trifluormetilnu skupinu; R4 i R5 predstavljaju atom vodika, ili inače R4 i R5, s atomom ugljika koji ih nosi, tvore zasićeni prsten s 3 do 6 atoma ugljika i izborno sadrži 0 do 1 heteroatom koji se bira između O, N ili S; R6 predstavlja skupinu koju se bira između atoma vodika, atoma halogena, (C1-C6)alkilnu, (C3-C7)cikloalkilnu, (C3-C7)cikloalkil(C1-C6)alkilnu, nitro ili amino skupinu, skupinu NR7R8 ili COOR, arilnu skupinu ili skupinu NR7(SO2)R8 ili C(O)NR7R8; R, R7 i R8, međusobno neovisno, predstavljaju jednu ili više skupina koje se bira između atoma vodika, (C1-C6)alkilne, (C3-C7)cikloalkilne ili (C3-C7)cikloalkil(C1-C6)alkilne skupine, arilne ili aril(C1-C6)alkilenske skupine, ili inače R7 i R8 mogu, s atomom koji ih nosi, tvoriti zasićeni, djelomično nezasićeni ili nezasićeni prsten s 5 do 7 atoma ugljika i izborno dodatno sadrži heteroatom koji se bira između O, N ili S(O)m;W predstavlja metilensku ili skupinu C(O); m predstavlja cijeli broj, čije vrijednosti mogu biti 0, 1 ili 2; n predstavlja cijeli broj, čije vrijednosti mogu biti 1, 2, 3, 4, 5 ili 6; p predstavlja cijeli broj, čije vrijednosti mogu biti 2 ili 3; ugljik koji nosi benzilnu skupinu supstituiranu s R2 ima apsolutnu konfiguraciju S; iugljik koji nosi hidroksilnu skupinu ima apsolutnu konfiguraciju R, u obliku baze ili adicijske soli s kiselinom. Patent sadrži još 18 patentnih zahtjeva.
Claims (19)
1. Spoj prema formuli (I)
[image]
naznačen time što:
R1 predstavlja atom vodika, (C1-C10)alkilnu, (C3-C7)cikloalkilnu, (CH2)n-(C1-C6)alkenilnu, (CH2)n-(C1-C6)alkinilnu ili (C1-C6)alkil-Z-(C1-C6)alkilnu skupinu, gdje Z predstavlja heteroatom koji se bira između O, N i S(O)m, ili inače R1 predstavlja skupinu COOR, S(O)mR, arilnu ili aralkilnu skupinu; (C1-C10)alkilna, (C3-C7)cikloalkilna, (CH2)n-(C1-C6)alkenilna, (CH2)n-(C1-C6)alkinilna, (C1-C6)alkil-Z-(C1-C6)alkilna, arilna ili aralkilna skupina izborno su supstituirane s jednom ili više skupina koje se bira između atoma halogena, (C1-C6)alkilne, (C3-C7)cikloalkilne, halogen(C1-C6)alkilne, (C1-C6)alkoksi, halogen(C1-C6)alkoksi, skupine NR7R8, nitro, cijano skupine, skupine OR, COOR, C(O)NR7R8 ili S(O)mNR7R8;
R2 predstavlja jednu ili više skupina koje se bira između atoma vodika, atoma halogena, (C1-C6)alkilne, (C3-C7)cikloalkilne, (C1-C6)alkenilne, (C1-C6)alkinilne ili (C1-C6)alkil-Z-(C1-C6)alkilne skupine, gdje Z predstavlja heteroatom koji se bira između O, N i S(O)m, ili inače R2 predstavlja halogen(C1-C6)alkilnu, halogen(C1-C6)alkoksi, hidroksi, (C1-C6)alkoksi, nitro, cijano ili amino skupinu, skupinu NR7R8, COOR, C(O)NR7R8, O-C(O)(C1-C6)alkilnu ili skupinu S(O)m-NR7R8 ili arilnu skupinu, gdje arilna skupina može biti izborno supstituirana s jednom ili više skupina koje se bira između atoma halogena, (C1-C6)alkilne, (C3-C7)cikloalkilne, halogen(C1-C6)alkilne, (C1-C6)alkoksi, halogen(C1-C6)alkoksi skupine, skupine NR7R8, OR, nitro, cijano skupine, skupine COOR, C(O)NR7R8 ili S(O)mNR7R8;
R3 predstavlja trifluormetilnu skupinu;
R4 i R5 predstavljaju atom vodika, ili inače R4 i R5, s atomom ugljika koji ih nosi, tvore zasićeni prsten s 3 do 6 atoma ugljika i izborno sadrži 0 do 1 heteroatom koji se bira između O, N ili S;
R6 predstavlja skupinu koju se bira između atoma vodika, atoma halogena, (C1-C6)alkilnu, (C3-C7)cikloalkilnu, (C3-C7)cikloalkil(C1-C6)alkilnu, nitro ili amino skupinu, skupinu NR7R8 ili COOR, arilnu skupinu ili skupinu NR7(SO2)R8 ili C(O)NR7R8;
R, R7 i R8, međusobno neovisno, predstavljaju jednu ili više skupina koje se bira između atoma vodika, (C1-C6)alkilne, (C3-C7)cikloalkilne ili (C3-C7)cikloalkil(C1-C6)alkilne skupine, arilne ili aril(C1-C6)alkilenske skupine, ili inače R7 i R8 mogu, s atomom koji ih nosi, tvoriti zasićeni, djelomično nezasićeni ili nezasićeni prsten s 5 do 7 atoma ugljika i izborno dodatno sadrži heteroatom koji se bira između O, N ili S(O)m;
W predstavlja metilensku ili skupinu C(O);
m predstavlja cijeli broj, čije vrijednosti mogu biti 0, 1 ili 2;
n predstavlja cijeli broj, čije vrijednosti mogu biti 1, 2, 3, 4, 5 ili 6;
p predstavlja cijeli broj, čije vrijednosti mogu biti 2 ili 3;
ugljik koji nosi benzilnu skupinu supstituiranu s R2 ima apsolutnu konfiguraciju S; i
ugljik koji nosi hidroksilnu skupinu ima apsolutnu konfiguraciju R, u obliku baze ili adicijske soli s kiselinom.
2. Spoj formule (I) u skladu s patentnim zahtjevom 1, naznačen time što W predstavlja metilensku skupinu, u obliku baze ili adicijske soli s kiselinom.
3. Spoj formule (I) u skladu s bilo kojim od patentnih zahtjeva 1 i 2, naznačen time što W predstavlja skupinu C(O), u obliku baze ili adicijske soli s kiselinom.
4. Spoj formule (I) u skladu s bilo kojim od patentnih zahtjeva 1 do 3, naznačen time što p predstavlja 2, u obliku baze ili adicijske soli s kiselinom.
5. Spoj formule (I) u skladu s bilo kojim od patentnih zahtjeva 1 do 3, naznačen time što p predstavlja 3, u obliku baze ili adicijske soli s kiselinom.
6. Spoj formule (I) u skladu s bilo kojim od patentnih zahtjeva 1 do 5, naznačen time što R6 predstavlja skupinu koju se bira između atoma vodika, skupine COOR ili skupine C(O)NR7R8, u obliku baze ili adicijske soli s kiselinom.
7. Spoj formule (I) u skladu s bilo kojim od patentnih zahtjeva 1 do 6, naznačen time što R6 predstavlja skupinu koju se bira između atoma vodika, skupine COOH ili COOMe ili skupine C(O)N(Et)2, u obliku baze ili adicijske soli s kiselinom.
8. Spoj formule (I) u skladu s bilo kojim od patentnih zahtjeva 1 do 7, naznačen time što:
W predstavlja metilensku ili skupinu C(O);
p predstavlja 2 ili 3;
R1 predstavlja atom vodika, (C1-C10)alkilnu, skupinu COOR ili S(O)mR, gdje je (C1-C10)alkilna skupina, izborno supstituirana s jednom ili više (C1-C6)alkilnih skupina;
R2 predstavlja jednu ili više skupina koje se bira između atoma vodika ili atoma halogena;
R4 i R5 predstavljaju atom vodika ili, s atomom ugljika koji ih nosi, tvore ciklopropilnu skupinu;
R6 predstavlja skupinu koju se bira između atoma vodika, skupine COOR ili skupine C(O)NR7R8; i
R, R7 i R8, međusobno neovisno, predstavljaju atom vodika ili jednu ili više (C1-C6)alkilnih skupina, u obliku baze ili adicijske soli s kiselinom.
9. Spoj formule (I) u skladu s bilo kojim od patentnih zahtjeva 1 do 8, naznačen time što ga se bira između:
• 2-tert-butil-8-metil-6-{[(1S,2R)-1-benzil-2-hidroksi-3-({1-[3-(trifluormetil)fenil]ciklopropil}amino)propil]karbamoil}-3,4-dihidropirolo[1,2-a]pirazin-2,8(1H)-dikarboksilata;
• 6-{[(1S,2R)-1-benzil-2-hidroksi-3-({1-[3-(trifluormetil)fenil]ciklopropil}amino)propil]karbamoil}-2-(tert-butoksikarbonil)-1,2,3,4-tetrahidropirolo[1,2-a]pirazin-8-karboksilne kiseline;
• hidroklorida 6-{[(1S,2R)-1-benzil-2-hidroksi-3-({1-[3-(trifluormetil)fenil]ciklopropil}amino)propil]karbamoil}-1,2,3,4-tetrahidropirolo[1,2-a]pirazin-8-karboksilne kiseline (2:1);
• tert-butil-6-{[(1S,2R)-1-benzil-2-hidroksi-3-({1-[3-(trifluormetil)fenil]ciklopropil}amino)propil]karbamoil}-8-(dietilkarbamoil)-3,4-dihidropirolo[1,2-a]pirazin-2(1H)-karboksilata;
• 6-{(1S,2R)-1-benzil-2-hidroksi-3-[1-(3-trifluormetilfenil)ciklopropilamino]propil}-N-8,N-8-dietil-1,2,3,4-tetrahidropirolo[1,2-a]pirazin-6,8-dikarboksamida i njegovog hidroklorida (2:1);
• 6-{(1S,2R)-1-benzil-2-hidroksi-3-[1-(3-trifluormetilfenil)ciklopropilamino]propil}-N-8,N-8-dietil-2-(metilsulfonil)-1,2,3,4-tetrahidropirolo[1,2-a]pirazin-6,8-dikarboksamida;
• N-[(1S,2R)-1-(3,5-difluorbenzil)-2-hidroksi-3-({1-[3-(trifluormetil)fenil]ciklopropil}amino)propil]-1-okso-2-(1-propilbutil)-1,2,3,4-tetrahidropirolo[1,2-a]pirazin-6-karboksamida i njegovog hidroklorida (1:1);
• N-[(1S,2R)-1-benzil-2-hidroksi-3-({1-[3-(trifluormetil)fenil]ciklopropil}amino)propil]-1-okso-2-(1-propilbutil)-1,2,3,4-tetrahidropirolo[1,2-a]pirazin-6-karboksamida i njegovog hidroklorida (1:1);
• N-[(1S,2R)-1-benzil-2-hidroksi-3-{[3-(trifluormetil)benzil]amino}propil]-1-okso-2-(1-propilbutil)-1,2,3,4-tetrahidropirolo[1,2-a]pirazin-6-karboksamida i njegovog hidroklorida (1:1);
• N-[(1S,2R)-1-benzil-2-hidroksi-3-{[3-(trifluormetil)benzil]amino}propil]-2-(1-etilpropil)-1-okso-1,2,3,4-tetrahidropirolo[1,2-a]pirazin-6-karboksamida i njegovog hidroklorida (1:1); i
• N-[(1S,2R)-1-benzil-2-hidroksi-3-{[3-(trifluormetil)benzil]amino}propil]-1-okso-2-(1-propilbutil)-2,3,4,5-tetrahidro-1H-pirolo[1,2-a][1,4]diazepin-7-karboksamida i njegovog hidroklorida (1:1).
10. Spoj formule (IIIa)
[image]
naznačen time što R1 i R6 su kao što je definirano u općoj formuli (I) u skladu s patentnim zahtjevom 1.
11. Spoj formule (IIIb)
[image]
naznačen time što R1 i R6 su kao što je definirano u općoj formuli (I) u skladu s patentnim zahtjevom 1.
12. Spoj u skladu s patentnim zahtjevom 11, naznačen time što spoj formule (IIIb) je 2-(tert-butoksikarbonil)-8-(metoksikarbonil)-1,2,3,4-tetrahidropirolo[1,2-a]pirazin-6-karboksilna kiselina.
13. Spoj formule (IIIc)
[image]
naznačen time što R1 i R6 su kao što je definirano u općoj formuli (I) u skladu s patentnim zahtjevom 1.
14. Medikament, naznačen time što sadrži spoj formule (I) u skladu s bilo kojim od patentnih zahtjeva 1 do 9, ili adicijsku sol tog spoja s farmaceutski prihvatljivom kiselinom.
15. Farmaceutski pripravak, naznačen time što sadrži spoj formule (I) u skladu s bilo kojim od patentnih zahtjeva 1 do 9, ili farmaceutski prihvatljivu sol, a također i najmanje jednu farmaceutski prihvatljivu pomoćnu tvar.
16. Upotreba spoja formule (I) u skladu s bilo kojim od patentnih zahtjeva 1 do 9, naznačena time što je navedeni lijek namijenjen pripravi medikamenta namijenjenog liječenju i/ili sprječavanju Alzheimerove bolesti, Parkinsonove bolesti, Huntingtonove bolesti, Creutzfeldt-Jakobove bolesti, Downovog sindroma, demencije s Lewyjevim tijelima, senilne demencije, frontotemporalne demencije, cerebralne i sistemične amiloidoze, blagih kognitivnih poremećaja, cerebralne amiloidne angiopatije, primarnih i sekundarnih poremećaja pamćenja, amiotrofne lateralne skleroze, multiple skleroze, perifernih neuropatija, dijabetičnih neuropatije, migrene, poremećaja raspoloženja, depresije, anksioznosti, vaskularnih poremećaja, poput ateroskleroze, cerebrovaskularne ishemije, tumora i poremećaja stanične proliferacije.
17. Upotreba spoja formule (I) u skladu s bilo kojim od patentnih zahtjeva 1 do 9, naznačena time što je navedeni lijek namijenjen pripravi medikamenta namijenjenog liječenju i/ili sprječavanju Alzheimerove bolesti, Parkinsonove bolesti, Downovog sindroma, demencije s Lewyjevim tijelima, senilne demencije, frontotemporalne demencije, cerebralne i sistemične amiloidoze, blagih kognitivnih poremećaja, cerebralne amiloidne angiopatije, primarnih i sekundarnih poremećaja pamćenja i cerebrovaskularne ishemije.
18. Spoj formule (I) u skladu s bilo kojim od patentnih zahtjeva 1 do 9, u obliku baze, naznačen time što je namijenjen sprječavanju ili liječenju Alzheimerove bolesti, Parkinsonove bolesti, Huntingtonove bolesti, Creutzfeldt-Jakobove bolesti, Downovog sindroma, demencije s Lewyjevim tijelima, senilne demencije, frontotemporalne demencije, cerebralne i sistemične amiloidoze, blagih kognitivnih poremećaja, cerebralne amiloidne angiopatije, primarnih i sekundarnih poremećaja pamćenja, amiotrofne lateralne skleroze, multiple skleroze, perifernih neuropatija, dijabetičnih neuropatija, migrene, poremećaja raspoloženja, depresije, anksioznosti, vaskularnih poremećaja, poput ateroskleroze, cerebrovaskularne ishemije, tumora i poremećaja stanične proliferacije.
19. Spoj formule (I) u skladu s bilo kojim od patentnih zahtjeva 1 do 9, u obliku baze, naznačen time što je namijenjen pripravi medikamenta namijenjenog liječenju i/ili sprječavanju Alzheimerove bolesti, Parkinsonove bolesti, Downovog sindroma, demencije s Lewyjevim tijelima, senilne demencije, frontotemporalne demencije, cerebralne i sistemične amiloidoze, blagih kognitivnih poremećaja, cerebralne amiloidne angiopatije, primarnih i sekundarnih poremećaja pamćenja i cerebrovaskularne ishemije.
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| PCT/FR2008/001096 WO2009044007A2 (fr) | 2007-07-27 | 2008-07-24 | Dérivés de 1,2,3,4-tetrahydropyrrolo[1,2-a]pyrazine-6-carboxamides et de 2,3,4,5-tetrahydropyrrolo[1,2-a][1,4]-diazépine-7-carboxamides, leur préparation et leur application en thérapeutique |
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| CA2860933C (en) * | 2012-02-03 | 2020-01-14 | Sanofi | Fused pyrroledicarboxamides and their use as pharmaceuticals |
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2008
- 2008-07-24 SI SI200830365T patent/SI2185561T1/sl unknown
- 2008-07-24 EA EA201070195A patent/EA201070195A1/ru unknown
- 2008-07-24 WO PCT/FR2008/001096 patent/WO2009044007A2/fr active Application Filing
- 2008-07-24 CA CA2694288A patent/CA2694288A1/fr not_active Abandoned
- 2008-07-24 AT AT08836692T patent/ATE512968T1/de active
- 2008-07-24 PL PL08836692T patent/PL2185561T3/pl unknown
- 2008-07-24 KR KR1020107001731A patent/KR20100050485A/ko not_active Application Discontinuation
- 2008-07-24 AU AU2008306835A patent/AU2008306835A1/en not_active Abandoned
- 2008-07-24 DK DK08836692.7T patent/DK2185561T3/da active
- 2008-07-24 EP EP08836692A patent/EP2185561B1/fr active Active
- 2008-07-24 RS RS20110374A patent/RS51912B/en unknown
- 2008-07-24 NZ NZ582871A patent/NZ582871A/en not_active IP Right Cessation
- 2008-07-24 BR BRPI0813094-9A2A patent/BRPI0813094A2/pt not_active IP Right Cessation
- 2008-07-24 CN CN200880100661.4A patent/CN101765601A/zh active Pending
- 2008-07-24 PT PT08836692T patent/PT2185561E/pt unknown
- 2008-07-24 MX MX2010001076A patent/MX2010001076A/es active IP Right Grant
- 2008-07-24 JP JP2010517449A patent/JP2010534639A/ja not_active Withdrawn
-
2010
- 2010-01-26 US US12/693,601 patent/US20100197668A1/en not_active Abandoned
- 2010-01-26 CO CO10007695A patent/CO6290689A2/es not_active Application Discontinuation
- 2010-01-26 ZA ZA2010/00581A patent/ZA201000581B/en unknown
- 2010-02-24 MA MA32647A patent/MA31630B1/fr unknown
-
2011
- 2011-09-09 HR HR20110650T patent/HRP20110650T1/hr unknown
- 2011-09-15 CY CY20111100888T patent/CY1112121T1/el unknown
Also Published As
| Publication number | Publication date |
|---|---|
| JP2010534639A (ja) | 2010-11-11 |
| AU2008306835A1 (en) | 2009-04-09 |
| ZA201000581B (en) | 2011-04-28 |
| PL2185561T3 (pl) | 2011-11-30 |
| SI2185561T1 (sl) | 2011-10-28 |
| MA31630B1 (fr) | 2010-08-02 |
| CY1112121T1 (el) | 2015-11-04 |
| EA201070195A1 (ru) | 2010-10-29 |
| ATE512968T1 (de) | 2011-07-15 |
| EP2185561A2 (fr) | 2010-05-19 |
| WO2009044007A3 (fr) | 2009-09-17 |
| EP2185561B1 (fr) | 2011-06-15 |
| BRPI0813094A2 (pt) | 2014-12-23 |
| CO6290689A2 (es) | 2011-06-20 |
| MX2010001076A (es) | 2010-03-09 |
| NZ582871A (en) | 2011-09-30 |
| PT2185561E (pt) | 2011-09-07 |
| US20100197668A1 (en) | 2010-08-05 |
| DK2185561T3 (da) | 2011-10-10 |
| RS51912B (en) | 2012-02-29 |
| WO2009044007A2 (fr) | 2009-04-09 |
| KR20100050485A (ko) | 2010-05-13 |
| CN101765601A (zh) | 2010-06-30 |
| CA2694288A1 (fr) | 2009-04-09 |
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