BG64176B1 - Бензил(илиден)лактамови производни, тяхното получаване и използването им като селективни антагонисти/агонисти на 5-нт1а и/или 5-нт1d рецептори - Google Patents
Бензил(илиден)лактамови производни, тяхното получаване и използването им като селективни антагонисти/агонисти на 5-нт1а и/или 5-нт1d рецептори Download PDFInfo
- Publication number
- BG64176B1 BG64176B1 BG102791A BG10279198A BG64176B1 BG 64176 B1 BG64176 B1 BG 64176B1 BG 102791 A BG102791 A BG 102791A BG 10279198 A BG10279198 A BG 10279198A BG 64176 B1 BG64176 B1 BG 64176B1
- Authority
- BG
- Bulgaria
- Prior art keywords
- disorders
- methylpiperazin
- benzylidene
- compound
- alkyl
- Prior art date
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- 239000005557 antagonist Substances 0.000 title claims abstract description 9
- 238000002360 preparation method Methods 0.000 title claims description 16
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 title claims description 5
- 239000000556 agonist Substances 0.000 title abstract description 11
- 150000001875 compounds Chemical class 0.000 claims abstract description 171
- 150000003839 salts Chemical class 0.000 claims abstract description 56
- -1 chloro, fluoro, bromo, iodo Chemical group 0.000 claims abstract description 43
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 34
- 239000001257 hydrogen Substances 0.000 claims abstract description 31
- 125000001072 heteroaryl group Chemical group 0.000 claims abstract description 20
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 18
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims abstract description 17
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 17
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 16
- 125000003118 aryl group Chemical group 0.000 claims abstract description 15
- 125000001424 substituent group Chemical group 0.000 claims abstract description 14
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims abstract description 14
- 125000001624 naphthyl group Chemical group 0.000 claims abstract description 12
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims abstract description 11
- 125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 8
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 8
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims abstract description 7
- 239000003795 chemical substances by application Substances 0.000 claims abstract description 6
- 125000005842 heteroatom Chemical group 0.000 claims abstract description 6
- 125000004433 nitrogen atom Chemical group N* 0.000 claims abstract description 6
- 125000004076 pyridyl group Chemical group 0.000 claims abstract description 6
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims abstract description 5
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 5
- 229910052760 oxygen Chemical group 0.000 claims abstract description 5
- 239000001301 oxygen Chemical group 0.000 claims abstract description 5
- 125000003831 tetrazolyl group Chemical group 0.000 claims abstract description 5
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims abstract description 4
- 125000002883 imidazolyl group Chemical group 0.000 claims abstract description 4
- 125000000896 monocarboxylic acid group Chemical group 0.000 claims abstract description 4
- 125000001786 isothiazolyl group Chemical group 0.000 claims abstract description 3
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims abstract description 3
- 125000002971 oxazolyl group Chemical group 0.000 claims abstract description 3
- 125000003226 pyrazolyl group Chemical group 0.000 claims abstract description 3
- 125000000335 thiazolyl group Chemical group 0.000 claims abstract description 3
- 125000001544 thienyl group Chemical group 0.000 claims abstract description 3
- 125000001425 triazolyl group Chemical group 0.000 claims abstract description 3
- QZAYGJVTTNCVMB-UHFFFAOYSA-N serotonin Chemical compound C1=C(O)C=C2C(CCN)=CNC2=C1 QZAYGJVTTNCVMB-UHFFFAOYSA-N 0.000 claims description 108
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 80
- 208000035475 disorder Diseases 0.000 claims description 76
- 238000011282 treatment Methods 0.000 claims description 46
- 241000124008 Mammalia Species 0.000 claims description 26
- 239000003112 inhibitor Substances 0.000 claims description 26
- 229960002073 sertraline Drugs 0.000 claims description 18
- VGKDLMBJGBXTGI-SJCJKPOMSA-N sertraline Chemical compound C1([C@@H]2CC[C@@H](C3=CC=CC=C32)NC)=CC=C(Cl)C(Cl)=C1 VGKDLMBJGBXTGI-SJCJKPOMSA-N 0.000 claims description 18
- 239000000126 substance Substances 0.000 claims description 18
- 108091032151 5-hydroxytryptamine receptor family Proteins 0.000 claims description 17
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- 208000018737 Parkinson disease Diseases 0.000 claims description 17
- 239000003814 drug Substances 0.000 claims description 17
- 230000005062 synaptic transmission Effects 0.000 claims description 16
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- 206010036596 premature ejaculation Diseases 0.000 claims description 14
- 230000002265 prevention Effects 0.000 claims description 14
- 238000011321 prophylaxis Methods 0.000 claims description 14
- 230000000862 serotonergic effect Effects 0.000 claims description 14
- 125000004195 4-methylpiperazin-1-yl group Chemical group [H]C([H])([H])N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 claims description 13
- 206010020772 Hypertension Diseases 0.000 claims description 13
- 210000001035 gastrointestinal tract Anatomy 0.000 claims description 13
- 239000008194 pharmaceutical composition Substances 0.000 claims description 13
- 208000019899 phobic disease Diseases 0.000 claims description 13
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- 231100000869 headache Toxicity 0.000 claims description 12
- 230000004899 motility Effects 0.000 claims description 12
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- 102000040125 5-hydroxytryptamine receptor family Human genes 0.000 claims description 11
- 208000024827 Alzheimer disease Diseases 0.000 claims description 11
- 238000011049 filling Methods 0.000 claims description 11
- 206010050389 Cerebral ataxia Diseases 0.000 claims description 10
- 208000006561 Cluster Headache Diseases 0.000 claims description 10
- 208000017701 Endocrine disease Diseases 0.000 claims description 10
- 125000000217 alkyl group Chemical group 0.000 claims description 10
- 208000018912 cluster headache syndrome Diseases 0.000 claims description 10
- 230000002708 enhancing effect Effects 0.000 claims description 10
- 125000000649 benzylidene group Chemical group [H]C(=[*])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 9
- 206010009094 Chronic paroxysmal hemicrania Diseases 0.000 claims description 8
- 208000030814 Eating disease Diseases 0.000 claims description 8
- 208000019454 Feeding and Eating disease Diseases 0.000 claims description 8
- 208000007101 Muscle Cramp Diseases 0.000 claims description 8
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims description 8
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- 150000002431 hydrogen Chemical group 0.000 claims description 8
- 208000007777 paroxysmal Hemicrania Diseases 0.000 claims description 8
- HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 claims description 8
- 230000003042 antagnostic effect Effects 0.000 claims description 7
- 206010012335 Dependence Diseases 0.000 claims description 6
- 102000014630 G protein-coupled serotonin receptor activity proteins Human genes 0.000 claims description 6
- 229910052799 carbon Inorganic materials 0.000 claims description 6
- 125000004432 carbon atom Chemical group C* 0.000 claims description 5
- 125000003386 piperidinyl group Chemical group 0.000 claims description 5
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 5
- 239000004001 serotonin 1D antagonist Substances 0.000 claims description 5
- QUBOFKHGVPGAKC-UHFFFAOYSA-N 1-(3,4-dichlorophenyl)-3-[[5-fluoro-2-(4-methylpiperazin-1-yl)phenyl]methylidene]piperidin-2-one Chemical compound C1CN(C)CCN1C1=CC=C(F)C=C1C=C1C(=O)N(C=2C=C(Cl)C(Cl)=CC=2)CCC1 QUBOFKHGVPGAKC-UHFFFAOYSA-N 0.000 claims description 4
- TWFJKRVEOJPLHP-UHFFFAOYSA-N 3-[[2-(4-methylpiperazin-1-yl)phenyl]methyl]-1-phenylpyrrolidin-2-one Chemical compound C1CN(C)CCN1C1=CC=CC=C1CC1C(=O)N(C=2C=CC=CC=2)CC1 TWFJKRVEOJPLHP-UHFFFAOYSA-N 0.000 claims description 4
- OTIKXZGZQMSIQE-UHFFFAOYSA-N 3-[[2-(4-methylpiperazin-1-yl)phenyl]methylidene]-1-phenylpyrrolidin-2-one Chemical compound C1CN(C)CCN1C1=CC=CC=C1C=C1C(=O)N(C=2C=CC=CC=2)CC1 OTIKXZGZQMSIQE-UHFFFAOYSA-N 0.000 claims description 4
- 206010047163 Vasospasm Diseases 0.000 claims description 4
- 235000016709 nutrition Nutrition 0.000 claims description 4
- 230000035764 nutrition Effects 0.000 claims description 4
- 229910052717 sulfur Inorganic materials 0.000 claims description 4
- 239000011593 sulfur Substances 0.000 claims description 4
- SVUVRUJADOUWEN-UHFFFAOYSA-N 1-(3,4-difluorophenyl)-3-[[2-(4-methylpiperazin-1-yl)phenyl]methylidene]pyrrolidin-2-one Chemical compound C1CN(C)CCN1C1=CC=CC=C1C=C1C(=O)N(C=2C=C(F)C(F)=CC=2)CC1 SVUVRUJADOUWEN-UHFFFAOYSA-N 0.000 claims description 3
- YMYPGNNKKHIXNU-UHFFFAOYSA-N 1-(4-methylphenyl)-3-[[2-(4-methylpiperazin-1-yl)phenyl]methylidene]pyrrolidin-2-one Chemical compound C1CN(C)CCN1C1=CC=CC=C1C=C1C(=O)N(C=2C=CC(C)=CC=2)CC1 YMYPGNNKKHIXNU-UHFFFAOYSA-N 0.000 claims description 3
- GVZDDZHOCZYDBT-UHFFFAOYSA-N 3-[[2-(4-methylpiperazin-1-yl)phenyl]methylidene]-1h-indol-2-one Chemical compound C1CN(C)CCN1C1=CC=CC=C1C=C1C2=CC=CC=C2NC1=O GVZDDZHOCZYDBT-UHFFFAOYSA-N 0.000 claims description 3
- GJKSPFSIHQBAAA-UHFFFAOYSA-N 3-[[4-fluoro-2-(4-methylpiperazin-1-yl)phenyl]methylidene]-1-phenylpyrrolidin-2-one Chemical compound C1CN(C)CCN1C1=CC(F)=CC=C1C=C1C(=O)N(C=2C=CC=CC=2)CC1 GJKSPFSIHQBAAA-UHFFFAOYSA-N 0.000 claims description 3
- 125000004604 benzisothiazolyl group Chemical group S1N=C(C2=C1C=CC=C2)* 0.000 claims description 3
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 claims description 3
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- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims description 3
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- 125000000168 pyrrolyl group Chemical group 0.000 claims description 3
- OEFLQFJSZMVNQS-UHFFFAOYSA-N 1-(3,4-dichlorophenyl)-3-[[2-(4-methylpiperazin-1-yl)phenyl]methylidene]pyrrolidin-2-one Chemical compound C1CN(C)CCN1C1=CC=CC=C1C=C1C(=O)N(C=2C=C(Cl)C(Cl)=CC=2)CC1 OEFLQFJSZMVNQS-UHFFFAOYSA-N 0.000 claims description 2
- BTYTYIJITBBUAC-UHFFFAOYSA-N 1-(3,4-dichlorophenyl)-3-[[5-fluoro-2-(4-methylpiperazin-1-yl)phenyl]methylidene]pyrrolidin-2-one Chemical compound C1CN(C)CCN1C1=CC=C(F)C=C1C=C1C(=O)N(C=2C=C(Cl)C(Cl)=CC=2)CC1 BTYTYIJITBBUAC-UHFFFAOYSA-N 0.000 claims description 2
- LWCHTDNWGXRROT-UHFFFAOYSA-N 1-(3,4-difluorophenyl)-3-[[2-(4-methylpiperazin-1-yl)phenyl]methyl]pyrrolidin-2-one Chemical compound C1CN(C)CCN1C1=CC=CC=C1CC1C(=O)N(C=2C=C(F)C(F)=CC=2)CC1 LWCHTDNWGXRROT-UHFFFAOYSA-N 0.000 claims description 2
- NBRKHSQLNPOVMR-UHFFFAOYSA-N 1-(4-chlorophenyl)-3-[[5-fluoro-2-(4-methylpiperazin-1-yl)phenyl]methylidene]piperidin-2-one Chemical compound C1CN(C)CCN1C1=CC=C(F)C=C1C=C1C(=O)N(C=2C=CC(Cl)=CC=2)CCC1 NBRKHSQLNPOVMR-UHFFFAOYSA-N 0.000 claims description 2
- FLKALFUHLVCIIN-UHFFFAOYSA-N 1-[(3,4-dichlorophenyl)methyl]-3-[[2-(4-methylpiperazin-1-yl)phenyl]methylidene]piperidin-2-one Chemical compound C1CN(C)CCN1C1=CC=CC=C1C=C1C(=O)N(CC=2C=C(Cl)C(Cl)=CC=2)CCC1 FLKALFUHLVCIIN-UHFFFAOYSA-N 0.000 claims description 2
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- VILVQZDPIFCZSB-UHFFFAOYSA-N 3-[[2-(4-methylpiperazin-1-yl)phenyl]methylidene]-1-[4-(trifluoromethyl)phenyl]pyrrolidin-2-one Chemical compound C1CN(C)CCN1C1=CC=CC=C1C=C1C(=O)N(C=2C=CC(=CC=2)C(F)(F)F)CC1 VILVQZDPIFCZSB-UHFFFAOYSA-N 0.000 claims description 2
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- WXUKTUAHUGLOSG-UHFFFAOYSA-N 3-[[5-fluoro-2-(4-methylpiperazin-1-yl)phenyl]methylidene]pyrrolidin-2-one Chemical compound C1CN(C)CCN1C1=CC=C(F)C=C1C=C1C(=O)NCC1 WXUKTUAHUGLOSG-UHFFFAOYSA-N 0.000 claims description 2
- FHFDVGZHHVTHEK-UHFFFAOYSA-N 5-chloro-3-[[2-(4-methylpiperazin-1-yl)phenyl]methylidene]-1h-indol-2-one Chemical compound C1CN(C)CCN1C1=CC=CC=C1C=C1C2=CC(Cl)=CC=C2NC1=O FHFDVGZHHVTHEK-UHFFFAOYSA-N 0.000 claims description 2
- OPSDVIJHGJHJNS-UHFFFAOYSA-N 6-chloro-3-[[2-(4-methylpiperazin-1-yl)phenyl]methylidene]-1h-indol-2-one Chemical compound C1CN(C)CCN1C1=CC=CC=C1C=C1C2=CC=C(Cl)C=C2NC1=O OPSDVIJHGJHJNS-UHFFFAOYSA-N 0.000 claims description 2
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- KQCKXYYIIYEARL-UHFFFAOYSA-N 1-(3,4-dichlorophenyl)-3-[[2-(4-methylpiperazin-1-yl)phenyl]methyl]piperidin-2-one Chemical compound C1CN(C)CCN1C1=CC=CC=C1CC1C(=O)N(C=2C=C(Cl)C(Cl)=CC=2)CCC1 KQCKXYYIIYEARL-UHFFFAOYSA-N 0.000 claims 1
- DHEGHIMXBFHOJK-UHFFFAOYSA-N 1-(3,4-dichlorophenyl)-3-[[2-[2-(dimethylamino)ethoxy]phenyl]methylidene]pyrrolidin-2-one Chemical compound CN(C)CCOC1=CC=CC=C1C=C1C(=O)N(C=2C=C(Cl)C(Cl)=CC=2)CC1 DHEGHIMXBFHOJK-UHFFFAOYSA-N 0.000 claims 1
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- LNKUUOUGABSERJ-UHFFFAOYSA-N 1-(3,4-dichlorophenyl)-3-[[5-fluoro-2-(4-methylpiperazin-1-yl)phenyl]methyl]piperidin-2-one Chemical compound C1CN(C)CCN1C1=CC=C(F)C=C1CC1C(=O)N(C=2C=C(Cl)C(Cl)=CC=2)CCC1 LNKUUOUGABSERJ-UHFFFAOYSA-N 0.000 claims 1
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Classifications
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- 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
- C07D207/18—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 one double bond between ring members or between a ring member and a non-ring member
- C07D207/22—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 one double bond between ring members or between a ring member and a non-ring member 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
- C07D207/24—Oxygen or sulfur atoms
- C07D207/26—2-Pyrrolidones
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- 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
- C07D207/38—2-Pyrrolones
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/30—Indoles; Hydrogenated indoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to carbon atoms of the hetero ring
- C07D209/32—Oxygen atoms
- C07D209/34—Oxygen atoms in position 2
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/68—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member
- C07D211/72—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, directly attached to ring carbon atoms
- C07D211/74—Oxygen atoms
- C07D211/76—Oxygen atoms attached in position 2 or 6
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/80—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings 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
- C07D211/84—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings 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 directly attached to ring carbon atoms
- C07D211/86—Oxygen atoms
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- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Neurosurgery (AREA)
- Neurology (AREA)
- Biomedical Technology (AREA)
- Obesity (AREA)
- Cardiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Pain & Pain Management (AREA)
- Hematology (AREA)
- Diabetes (AREA)
- Rheumatology (AREA)
- Psychiatry (AREA)
- Endocrinology (AREA)
- Child & Adolescent Psychology (AREA)
- Psychology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Hydrogenated Pyridines (AREA)
- Other In-Based Heterocyclic Compounds (AREA)
- Pyrrole Compounds (AREA)
- Indole Compounds (AREA)
- Quinoline Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US1513496P | 1996-03-29 | 1996-03-29 | |
| PCT/IB1997/000076 WO1997036867A1 (en) | 1996-03-29 | 1997-02-03 | Benzyl(idene)-lactam derivatives, their preparation and their use as selective (ant)agonists of 5-ht1a- and/or 5-ht1d receptors |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| BG102791A BG102791A (en) | 1999-11-30 |
| BG64176B1 true BG64176B1 (bg) | 2004-03-31 |
Family
ID=21769713
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| BG102791A BG64176B1 (bg) | 1996-03-29 | 1998-09-24 | Бензил(илиден)лактамови производни, тяхното получаване и използването им като селективни антагонисти/агонисти на 5-нт1а и/или 5-нт1d рецептори |
Country Status (39)
| Country | Link |
|---|---|
| US (2) | US6462048B2 (cs) |
| EP (1) | EP0894085B1 (cs) |
| JP (1) | JP3118467B2 (cs) |
| KR (1) | KR100305071B1 (cs) |
| CN (1) | CN1128788C (cs) |
| AP (1) | AP824A (cs) |
| AR (1) | AR006390A1 (cs) |
| AT (1) | ATE302182T1 (cs) |
| AU (1) | AU706839B2 (cs) |
| BG (1) | BG64176B1 (cs) |
| BR (1) | BR9708581A (cs) |
| CA (1) | CA2249603A1 (cs) |
| CO (1) | CO4650033A1 (cs) |
| CZ (1) | CZ293628B6 (cs) |
| DE (1) | DE69733996T2 (cs) |
| DZ (1) | DZ2198A1 (cs) |
| EA (1) | EA001485B1 (cs) |
| ES (1) | ES2246058T3 (cs) |
| HN (1) | HN1997000023A (cs) |
| HR (1) | HRP970175A2 (cs) |
| HU (1) | HUP9902160A3 (cs) |
| ID (1) | ID17781A (cs) |
| IL (1) | IL125377A (cs) |
| IS (1) | IS4813A (cs) |
| MA (1) | MA26425A1 (cs) |
| MY (1) | MY118498A (cs) |
| NO (1) | NO312957B1 (cs) |
| NZ (1) | NZ325914A (cs) |
| OA (1) | OA10879A (cs) |
| PL (1) | PL329170A1 (cs) |
| SK (1) | SK131498A3 (cs) |
| TN (1) | TNSN97056A1 (cs) |
| TR (1) | TR199801929T2 (cs) |
| TW (1) | TW413679B (cs) |
| UA (1) | UA70284C2 (cs) |
| UY (1) | UY24498A1 (cs) |
| WO (1) | WO1997036867A1 (cs) |
| YU (1) | YU11997A (cs) |
| ZA (1) | ZA972690B (cs) |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| JPH041367U (cs) * | 1990-04-13 | 1992-01-08 | ||
| US6906093B2 (en) | 1995-06-07 | 2005-06-14 | Sugen, Inc. | Indolinone combinatorial libraries and related products and methods for the treatment of disease |
| US5880141A (en) | 1995-06-07 | 1999-03-09 | Sugen, Inc. | Benzylidene-Z-indoline compounds for the treatment of disease |
| US6147106A (en) | 1997-08-20 | 2000-11-14 | Sugen, Inc. | Indolinone combinatorial libraries and related products and methods for the treatment of disease |
| US6696448B2 (en) | 1996-06-05 | 2004-02-24 | Sugen, Inc. | 3-(piperazinylbenzylidenyl)-2-indolinone compounds and derivatives as protein tyrosine kinase inhibitors |
| US6423708B1 (en) * | 1996-09-30 | 2002-07-23 | Pfizer Inc | Aralkyl and aralkylidene heterocyclic lactams and imides |
| UA56185C2 (uk) | 1996-09-30 | 2003-05-15 | Пфайзер Інк. | Аралкіл- та аралкіліденгетероциклічні лактами та іміди, фармацевтична композиція та спосіб лікування |
| GB9718913D0 (en) | 1997-09-05 | 1997-11-12 | Glaxo Group Ltd | Substituted oxindole derivatives |
| US6531502B1 (en) | 1998-01-21 | 2003-03-11 | Sugen, Inc. | 3-Methylidenyl-2-indolinone modulators of protein kinase |
| DE19830201A1 (de) * | 1998-07-07 | 2000-01-13 | Boehringer Ingelheim Pharma | Mittel mit antidepressiver Wirkung |
| CA2301899C (en) * | 1998-07-27 | 2008-11-18 | Boehringer Ingelheim Pharma Kg | Agent with an antidepressant activity |
| US6492398B1 (en) | 1999-03-04 | 2002-12-10 | Smithkline Beechman Corporation | Thiazoloindolinone compounds |
| GB9904933D0 (en) | 1999-03-04 | 1999-04-28 | Glaxo Group Ltd | Compounds |
| US6624171B1 (en) | 1999-03-04 | 2003-09-23 | Smithkline Beecham Corporation | Substituted aza-oxindole derivatives |
| ES2225031T3 (es) * | 1999-12-29 | 2005-03-16 | Pfizer Products Inc. | Compuestos de 3-((2-piperazinil-fenil)metil)-1-(4-(trifluorometil)fenil)-2-pirrolidinona opticamente activos como antagonistas selectivos del receptor de 5-ht1d. |
| KR100713960B1 (ko) | 2000-02-15 | 2007-05-02 | 수젠, 인크. | 피롤 치환 2-인돌리논 단백질 인산화 효소 저해제 |
| US6620818B1 (en) | 2000-03-01 | 2003-09-16 | Smithkline Beecham Corporation | Method for reducing the severity of side effects of chemotherapy and/or radiation therapy |
| AR042586A1 (es) | 2001-02-15 | 2005-06-29 | Sugen Inc | 3-(4-amidopirrol-2-ilmetiliden)-2-indolinona como inhibidores de la protein quinasa; sus composiciones farmaceuticas; un metodo para la modulacion de la actividad catalitica de la proteinquinasa; un metodo para tratar o prevenir una afeccion relacionada con la proteinquinasa |
| MXPA04003385A (es) | 2001-10-10 | 2005-04-11 | Sugen Inc | Derivados de 3-?4-substituido con heterociclilo)-pirrol-2-ilmetilidene?-2-indolinona como inhibidores de cinasa. |
| AU2003214800A1 (en) | 2002-01-02 | 2003-07-24 | Ardent Pharmaceuticals, Inc. | Method of treating sexual dysfunctions with delta opioid receptor agonist compounds |
| TWI263497B (en) * | 2002-03-29 | 2006-10-11 | Lilly Co Eli | Pyridinoylpiperidines as 5-HT1F agonists |
| WO2005051919A1 (en) * | 2003-11-26 | 2005-06-09 | Pfizer Products Inc. | Aminopyrazole derivatives as gsk-3 inhibitors |
| CA2553291A1 (en) * | 2004-01-29 | 2005-09-09 | Pfizer Products Inc. | Combination of .gamma.-aminobutyric acid modulators and 5-ht1b receptor antagonists |
| EP1727794B1 (en) * | 2004-03-17 | 2011-11-16 | Pfizer Products Inc. | Novel benzyl(idene)-lactam derivatives |
| CA2565996A1 (en) * | 2004-05-11 | 2005-11-17 | Pfizer Products Inc. | Combination of atypical antipsychotics and 5-ht1b receptor antagonists |
| MXPA06012347A (es) * | 2004-05-21 | 2007-01-17 | Pfizer Prod Inc | Derivados de pirazinilmetil-lactama. |
| EP1768975A2 (en) * | 2004-06-25 | 2007-04-04 | Pfizer Products Inc. | Pyridyl piperazines for the treatment of cns disorders |
| US8012969B2 (en) | 2005-01-13 | 2011-09-06 | Ge Healthcare Limited | 11C-labeled benzyl-lactam compounds and their use as imaging agents |
| WO2006106416A1 (en) * | 2005-04-08 | 2006-10-12 | Pfizer Products Inc. | PYRIDIL-LACTAMS AND THEIR USE 5 -HTl RECEPTORS LIGAN |
| JP2008543829A (ja) * | 2005-06-17 | 2008-12-04 | ファイザー・プロダクツ・インク | セロトニン受容体アンタゴニストとしての１−［６−（１−エチル−１−ヒドロキシ−プロピル）−ピリジン−３−イル］−３−［２−（４−メチル−ピペラジン−１−イル）−ベンジル］−ピロリジン−２−オンの代謝産物 |
| WO2007012964A1 (en) * | 2005-07-25 | 2007-02-01 | Pfizer Products Inc. | Preparation of alkylpiperazinylphenyl compounds by classical resolution |
| WO2007026224A2 (en) * | 2005-08-31 | 2007-03-08 | Pfizer Products Inc. | 5-ht1b antagonist composition for depression, anxiety and cognition |
| WO2007026219A2 (en) * | 2005-08-31 | 2007-03-08 | Pfizer Products Inc. | Combinations of a 5-ht1b antagonist with a noradrenalin re-uptake inhibitor or a serotonin noradrenalin reutake inhibitor for treating cns conditions |
| US20070096411A1 (en) * | 2005-11-02 | 2007-05-03 | Rempe Gary L Ii | Device for retaining a kneeling rider on a gliding board |
| EP3610890A1 (en) | 2012-11-14 | 2020-02-19 | The Johns Hopkins University | Methods and compositions for treating schizophrenia |
| PL3344248T3 (pl) | 2015-09-02 | 2022-07-18 | Trevena, Inc. | Zawierające sześcioczłonowy aza-heterocykl związki modulujące receptor opioidowy delta oraz sposoby ich wykorzystywania i wytwarzania |
| CN110520129A (zh) | 2017-02-17 | 2019-11-29 | 特维娜有限公司 | 含有5元氮杂杂环的δ阿片受体调节化合物及其使用和制备方法 |
| CN110446495B (zh) | 2017-02-17 | 2023-09-05 | 特维娜有限公司 | 含有7元氮杂杂环的δ阿片受体调节化合物及其使用和制备方法 |
| WO2020183011A1 (en) | 2019-03-14 | 2020-09-17 | Institut Curie | Htr1d inhibitors and uses thereof in the treatment of cancer |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| US4078062A (en) | 1976-10-28 | 1978-03-07 | E. R. Squibb & Sons, Inc. | Substituted 2H-1,4-benzothiazin-3(4H)-ones |
| JPS62116557A (ja) * | 1985-11-15 | 1987-05-28 | Takeda Chem Ind Ltd | 置換ベンジルラクタム類 |
| US5189179A (en) * | 1990-08-29 | 1993-02-23 | Merrell Dow Pharmaceuticals Inc. | Serotonin 5ht1a agonists |
| PT533268E (pt) | 1991-09-18 | 2002-02-28 | Glaxo Group Ltd | Derivados de benzanilida como antagonistas de 5-ht1d |
| ATE156123T1 (de) * | 1991-10-11 | 1997-08-15 | Du Pont Merck Pharma | Cyclische harnstoffe und analoga verwendbar als retrovirale proteasehemmer |
| US5436246A (en) | 1992-09-17 | 1995-07-25 | Merrell Dow Pharmaceuticals Inc. | Serotonin receptor agents |
| GB9410512D0 (en) * | 1994-05-25 | 1994-07-13 | Smithkline Beecham Plc | Novel treatment |
| US5880141A (en) * | 1995-06-07 | 1999-03-09 | Sugen, Inc. | Benzylidene-Z-indoline compounds for the treatment of disease |
| US6467084B1 (en) * | 1999-12-16 | 2002-10-15 | Emware, Inc. | Systems and methods for reprogramming an embedded device with program code using relocatable program code |
-
1997
- 1997-02-03 JP JP09535074A patent/JP3118467B2/ja not_active Expired - Fee Related
- 1997-02-03 PL PL97329170A patent/PL329170A1/xx unknown
- 1997-02-03 CA CA002249603A patent/CA2249603A1/en not_active Abandoned
- 1997-02-03 SK SK1314-98A patent/SK131498A3/sk unknown
- 1997-02-03 BR BR9708581A patent/BR9708581A/pt not_active Application Discontinuation
- 1997-02-03 AT AT97900717T patent/ATE302182T1/de not_active IP Right Cessation
- 1997-02-03 WO PCT/IB1997/000076 patent/WO1997036867A1/en not_active Ceased
- 1997-02-03 DE DE69733996T patent/DE69733996T2/de not_active Expired - Fee Related
- 1997-02-03 ES ES97900717T patent/ES2246058T3/es not_active Expired - Lifetime
- 1997-02-03 TR TR1998/01929T patent/TR199801929T2/xx unknown
- 1997-02-03 NZ NZ325914A patent/NZ325914A/en unknown
- 1997-02-03 EP EP97900717A patent/EP0894085B1/en not_active Expired - Lifetime
- 1997-02-03 US US09/155,215 patent/US6462048B2/en not_active Expired - Fee Related
- 1997-02-03 KR KR1019980707713A patent/KR100305071B1/ko not_active Expired - Fee Related
- 1997-02-03 CZ CZ19983052A patent/CZ293628B6/cs not_active IP Right Cessation
- 1997-02-03 AU AU13170/97A patent/AU706839B2/en not_active Ceased
- 1997-02-03 CN CN97193251A patent/CN1128788C/zh not_active Expired - Fee Related
- 1997-02-03 EA EA199800771A patent/EA001485B1/ru not_active IP Right Cessation
- 1997-02-03 IL IL12537797A patent/IL125377A/xx not_active IP Right Cessation
- 1997-02-03 HU HU9902160A patent/HUP9902160A3/hu unknown
- 1997-02-04 TW TW086101295A patent/TW413679B/zh active
- 1997-02-06 HN HN1997000023A patent/HN1997000023A/es unknown
- 1997-03-02 UA UA98095077A patent/UA70284C2/uk unknown
- 1997-03-13 CO CO97013714A patent/CO4650033A1/es unknown
- 1997-03-21 UY UY24498A patent/UY24498A1/es not_active IP Right Cessation
- 1997-03-25 AR ARP970101200A patent/AR006390A1/es not_active Application Discontinuation
- 1997-03-26 TN TNTNSN97056A patent/TNSN97056A1/fr unknown
- 1997-03-26 MA MA24535A patent/MA26425A1/fr unknown
- 1997-03-26 DZ DZ970045A patent/DZ2198A1/fr active
- 1997-03-26 HR HR60/015,134A patent/HRP970175A2/hr not_active Application Discontinuation
- 1997-03-27 ZA ZA972690A patent/ZA972690B/xx unknown
- 1997-03-27 YU YU11997A patent/YU11997A/sh unknown
- 1997-03-27 AP APAP/P/1997/000955A patent/AP824A/en active
- 1997-03-27 ID IDP971025A patent/ID17781A/id unknown
- 1997-03-28 MY MYPI97001340A patent/MY118498A/en unknown
-
1998
- 1998-07-29 IS IS4813A patent/IS4813A/is unknown
- 1998-09-16 OA OA9800170A patent/OA10879A/en unknown
- 1998-09-24 BG BG102791A patent/BG64176B1/bg unknown
- 1998-09-28 NO NO19984513A patent/NO312957B1/no unknown
-
2002
- 2002-08-15 US US10/219,692 patent/US6924289B2/en not_active Expired - Fee Related
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