HRP970175A2 - Lactam derivatives - Google Patents
Lactam derivativesInfo
- Publication number
- HRP970175A2 HRP970175A2 HR60/015,134A HRP970175A HRP970175A2 HR P970175 A2 HRP970175 A2 HR P970175A2 HR P970175 A HRP970175 A HR P970175A HR P970175 A2 HRP970175 A2 HR P970175A2
- Authority
- HR
- Croatia
- Prior art keywords
- methylpiperazin
- disorder
- benzylidene
- disorders
- pyrrolidin
- Prior art date
Links
- 150000003951 lactams Chemical class 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims description 173
- QZAYGJVTTNCVMB-UHFFFAOYSA-N serotonin Chemical compound C1=C(O)C=C2C(CCN)=CNC2=C1 QZAYGJVTTNCVMB-UHFFFAOYSA-N 0.000 claims description 70
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 66
- 208000035475 disorder Diseases 0.000 claims description 66
- 150000003839 salts Chemical group 0.000 claims description 61
- 238000000034 method Methods 0.000 claims description 56
- -1 chloro, fluoro, bromo, iodo Chemical group 0.000 claims description 42
- 241000124008 Mammalia Species 0.000 claims description 39
- 230000002265 prevention Effects 0.000 claims description 27
- 229910052739 hydrogen Inorganic materials 0.000 claims description 25
- 239000001257 hydrogen Substances 0.000 claims description 25
- 239000003112 inhibitor Substances 0.000 claims description 25
- 206010019233 Headaches Diseases 0.000 claims description 24
- 231100000869 headache Toxicity 0.000 claims description 24
- 238000010521 absorption reaction Methods 0.000 claims description 22
- 239000000126 substance Substances 0.000 claims description 22
- 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 21
- 208000018737 Parkinson disease Diseases 0.000 claims description 20
- 229960002073 sertraline Drugs 0.000 claims description 20
- 208000026139 Memory disease Diseases 0.000 claims description 19
- 208000019901 Anxiety disease Diseases 0.000 claims description 18
- 208000019695 Migraine disease Diseases 0.000 claims description 17
- 206010027599 migraine Diseases 0.000 claims description 17
- 206010012335 Dependence Diseases 0.000 claims description 16
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 15
- 125000000217 alkyl group Chemical group 0.000 claims description 15
- 230000036506 anxiety Effects 0.000 claims description 15
- 208000019906 panic disease Diseases 0.000 claims description 15
- 230000005062 synaptic transmission Effects 0.000 claims description 15
- 208000021384 Obsessive-Compulsive disease Diseases 0.000 claims description 14
- 239000000825 pharmaceutical preparation Substances 0.000 claims description 14
- 208000024827 Alzheimer disease Diseases 0.000 claims description 13
- 208000017701 Endocrine disease Diseases 0.000 claims description 13
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 13
- 208000002193 Pain Diseases 0.000 claims description 13
- 206010047163 Vasospasm Diseases 0.000 claims description 13
- 230000004899 motility Effects 0.000 claims description 13
- 208000019899 phobic disease Diseases 0.000 claims description 13
- 206010036596 premature ejaculation Diseases 0.000 claims description 13
- 230000028327 secretion Effects 0.000 claims description 13
- 208000011580 syndromic disease Diseases 0.000 claims description 13
- 206010008025 Cerebellar ataxia Diseases 0.000 claims description 12
- 206010020772 Hypertension Diseases 0.000 claims description 12
- 125000003118 aryl group Chemical group 0.000 claims description 12
- 239000003937 drug carrier Substances 0.000 claims description 12
- 150000002431 hydrogen Chemical class 0.000 claims description 12
- 208000007777 paroxysmal Hemicrania Diseases 0.000 claims description 12
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 12
- 125000001424 substituent group Chemical group 0.000 claims description 12
- 208000019553 vascular disease Diseases 0.000 claims description 12
- 102000040125 5-hydroxytryptamine receptor family Human genes 0.000 claims description 11
- 108091032151 5-hydroxytryptamine receptor family Proteins 0.000 claims description 11
- 206010009094 Chronic paroxysmal hemicrania Diseases 0.000 claims description 11
- 210000001035 gastrointestinal tract Anatomy 0.000 claims description 11
- 125000001072 heteroaryl group Chemical group 0.000 claims description 11
- 229910052757 nitrogen Inorganic materials 0.000 claims description 11
- 230000000862 serotonergic effect Effects 0.000 claims description 11
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 11
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 10
- 206010033307 Overweight Diseases 0.000 claims description 10
- 208000022821 personality disease Diseases 0.000 claims description 10
- 208000030814 Eating disease Diseases 0.000 claims description 9
- 208000019454 Feeding and Eating disease Diseases 0.000 claims description 9
- 230000001270 agonistic effect Effects 0.000 claims description 9
- 230000003042 antagnostic effect Effects 0.000 claims description 9
- 235000014632 disordered eating Nutrition 0.000 claims description 9
- 125000001624 naphthyl group Chemical group 0.000 claims description 9
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 8
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims description 8
- PXBRQCKWGAHEHS-UHFFFAOYSA-N dichlorodifluoromethane Chemical compound FC(F)(Cl)Cl PXBRQCKWGAHEHS-UHFFFAOYSA-N 0.000 claims description 8
- 229910052799 carbon Inorganic materials 0.000 claims description 7
- 230000027455 binding Effects 0.000 claims description 6
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 6
- 125000003545 alkoxy group Chemical group 0.000 claims description 5
- 125000003386 piperidinyl group Chemical group 0.000 claims description 5
- 239000003727 serotonin 1A antagonist Substances 0.000 claims description 5
- 239000004001 serotonin 1D antagonist Substances 0.000 claims description 5
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 4
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 4
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 4
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 4
- 125000005842 heteroatom Chemical group 0.000 claims description 4
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 4
- 239000001301 oxygen Substances 0.000 claims description 4
- 229910052760 oxygen Inorganic materials 0.000 claims description 4
- 125000004076 pyridyl group Chemical group 0.000 claims description 4
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 4
- 239000011593 sulfur Chemical group 0.000 claims description 4
- 229910052717 sulfur Inorganic materials 0.000 claims description 4
- 125000003831 tetrazolyl group Chemical group 0.000 claims description 4
- 125000000335 thiazolyl group Chemical group 0.000 claims description 4
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 3
- LZVAALHOUHRHEN-UHFFFAOYSA-N 1-[(3,4-dichlorophenyl)methyl]-3-[[2-(4-methylpiperazin-1-yl)phenyl]methylidene]indol-2-one Chemical compound C1CN(C)CCN1C1=CC=CC=C1C=C1C2=CC=CC=C2N(CC=2C=C(Cl)C(Cl)=CC=2)C1=O LZVAALHOUHRHEN-UHFFFAOYSA-N 0.000 claims description 3
- 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 3
- 125000004604 benzisothiazolyl group Chemical group S1N=C(C2=C1C=CC=C2)* 0.000 claims description 3
- 125000004603 benzisoxazolyl group Chemical group O1N=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
- 125000004541 benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 claims description 3
- 230000037406 food intake Effects 0.000 claims description 3
- 235000012631 food intake Nutrition 0.000 claims description 3
- 125000002883 imidazolyl group Chemical group 0.000 claims description 3
- 125000000896 monocarboxylic acid group Chemical group 0.000 claims description 3
- 125000004193 piperazinyl group Chemical group 0.000 claims description 3
- 125000000168 pyrrolyl group Chemical group 0.000 claims description 3
- CYRMSUTZVYGINF-UHFFFAOYSA-N trichlorofluoromethane Chemical compound FC(Cl)(Cl)Cl CYRMSUTZVYGINF-UHFFFAOYSA-N 0.000 claims description 3
- 125000006570 (C5-C6) heteroaryl group Chemical group 0.000 claims description 2
- 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 description 2
- 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 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
- WFZDDRBHAPGODK-UHFFFAOYSA-N 1-(4-methoxyphenyl)-3-[[2-(4-methylpiperazin-1-yl)phenyl]methylidene]-4h-quinolin-2-one Chemical compound C1=CC(OC)=CC=C1N(C1=O)C2=CC=CC=C2CC1=CC1=CC=CC=C1N1CCN(C)CC1 WFZDDRBHAPGODK-UHFFFAOYSA-N 0.000 claims description 2
- 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 2
- SSORKNRKKWDREJ-UHFFFAOYSA-N 1-[2-(4-chlorophenyl)ethyl]-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(CCC=2C=CC(Cl)=CC=2)CCC1 SSORKNRKKWDREJ-UHFFFAOYSA-N 0.000 claims description 2
- CVYOLTKZNMYOND-UHFFFAOYSA-N 1-methyl-3-[[2-(4-methylpiperazin-1-yl)phenyl]methylidene]indol-2-one Chemical compound C12=CC=CC=C2N(C)C(=O)C1=CC1=CC=CC=C1N1CCN(C)CC1 CVYOLTKZNMYOND-UHFFFAOYSA-N 0.000 claims description 2
- HRIJMEXHEDAGJI-UHFFFAOYSA-N 3-[[2-(4-methylpiperazin-1-yl)phenyl]methyl]-1-[4-(trifluoromethyl)phenyl]pyrrolidin-2-one Chemical compound C1CN(C)CCN1C1=CC=CC=C1CC1C(=O)N(C=2C=CC(=CC=2)C(F)(F)F)CC1 HRIJMEXHEDAGJI-UHFFFAOYSA-N 0.000 claims description 2
- 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 2
- VLRNGEYXRNXMKH-UHFFFAOYSA-N 3-[[2-(4-methylpiperazin-1-yl)phenyl]methyl]pyrrolidin-2-one Chemical compound C1CN(C)CCN1C1=CC=CC=C1CC1C(=O)NCC1 VLRNGEYXRNXMKH-UHFFFAOYSA-N 0.000 claims description 2
- FJPZQQXEVVFGPJ-UHFFFAOYSA-N 3-[[2-(4-methylpiperazin-1-yl)phenyl]methylidene]-1-phenylindol-2-one Chemical compound C1CN(C)CCN1C1=CC=CC=C1C=C1C2=CC=CC=C2N(C=2C=CC=CC=2)C1=O FJPZQQXEVVFGPJ-UHFFFAOYSA-N 0.000 claims description 2
- 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 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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- 230000002295 serotoninergic effect Effects 0.000 claims 5
- 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 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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Application Number | Priority Date | Filing Date | Title |
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US1513496P | 1996-03-29 | 1996-03-29 |
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HRP970175A2 true HRP970175A2 (en) | 1998-12-31 |
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HR60/015,134A HRP970175A2 (en) | 1996-03-29 | 1997-03-26 | Lactam derivatives |
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US (2) | US6462048B2 (sk) |
EP (1) | EP0894085B1 (sk) |
JP (1) | JP3118467B2 (sk) |
KR (1) | KR100305071B1 (sk) |
CN (1) | CN1128788C (sk) |
AP (1) | AP824A (sk) |
AR (1) | AR006390A1 (sk) |
AT (1) | ATE302182T1 (sk) |
AU (1) | AU706839B2 (sk) |
BG (1) | BG64176B1 (sk) |
BR (1) | BR9708581A (sk) |
CA (1) | CA2249603A1 (sk) |
CO (1) | CO4650033A1 (sk) |
CZ (1) | CZ293628B6 (sk) |
DE (1) | DE69733996T2 (sk) |
DZ (1) | DZ2198A1 (sk) |
EA (1) | EA001485B1 (sk) |
ES (1) | ES2246058T3 (sk) |
HK (1) | HK1019446A1 (sk) |
HN (1) | HN1997000023A (sk) |
HR (1) | HRP970175A2 (sk) |
HU (1) | HUP9902160A3 (sk) |
ID (1) | ID17781A (sk) |
IL (1) | IL125377A (sk) |
IS (1) | IS4813A (sk) |
MA (1) | MA26425A1 (sk) |
MY (1) | MY118498A (sk) |
NO (1) | NO312957B1 (sk) |
NZ (1) | NZ325914A (sk) |
OA (1) | OA10879A (sk) |
PL (1) | PL329170A1 (sk) |
SK (1) | SK131498A3 (sk) |
TN (1) | TNSN97056A1 (sk) |
TR (1) | TR199801929T2 (sk) |
TW (1) | TW413679B (sk) |
UA (1) | UA70284C2 (sk) |
UY (1) | UY24498A1 (sk) |
WO (1) | WO1997036867A1 (sk) |
YU (1) | YU11997A (sk) |
ZA (1) | ZA972690B (sk) |
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US5880141A (en) * | 1995-06-07 | 1999-03-09 | Sugen, Inc. | Benzylidene-Z-indoline compounds 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 |
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 |
WO2000006162A1 (de) * | 1998-07-27 | 2000-02-10 | Boehringer Ingelheim Pharma Kg | Mittel mit antidepressiver wirkung, mit pramipexol und einem weiteren antidepressivum |
US6624171B1 (en) | 1999-03-04 | 2003-09-23 | Smithkline Beecham Corporation | Substituted aza-oxindole derivatives |
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 |
EP1113015B1 (en) * | 1999-12-29 | 2004-09-15 | Pfizer Products Inc. | Optically active 3-((2-piperazinyl-phenyl)methyl)-1-(4-(trifluoromethyl)-phenyl)-2-pyrrolidinone compounds as 5-HT1D receptor selective antagonists |
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 |
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. |
EP1469850B1 (en) * | 2002-01-02 | 2013-01-02 | Versi Group, LLC | 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 |
EA200601461A1 (ru) | 2004-03-17 | 2007-02-27 | Пфайзер Продактс, Инк. | Новые производные бензил(иден)лактама |
JP2007537232A (ja) * | 2004-05-11 | 2007-12-20 | ファイザー・プロダクツ・インク | 非定型抗精神病薬と5−ht1b受容体拮抗薬の組合せ |
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 |
ATE521591T1 (de) * | 2005-01-13 | 2011-09-15 | Ge Healthcare Ltd | 11c-markierte benzyl-lactam-verbindungen und deren verwendung als bildgebungsmittel |
WO2006106416A1 (en) * | 2005-04-08 | 2006-10-12 | Pfizer Products Inc. | PYRIDIL-LACTAMS AND THEIR USE 5 -HTl RECEPTORS LIGAN |
CA2612268A1 (en) * | 2005-06-17 | 2006-12-28 | Pfizer Products Inc. | Metabolites of 1-[6-(1-ethyl-1-hydroxy-propyl)-pyridin-3-yl]-3-[2-(4-methyl-piperazin-1-yl)-benzyl]-pyrrolidin-2-one as seratonin receptor antagonists |
WO2007012964A1 (en) * | 2005-07-25 | 2007-02-01 | Pfizer Products Inc. | Preparation of alkylpiperazinylphenyl compounds by classical resolution |
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 |
WO2007026224A2 (en) * | 2005-08-31 | 2007-03-08 | Pfizer Products Inc. | 5-ht1b antagonist composition for depression, anxiety and cognition |
US20070096411A1 (en) * | 2005-11-02 | 2007-05-03 | Rempe Gary L Ii | Device for retaining a kneeling rider on a gliding board |
CA2891122C (en) | 2012-11-14 | 2021-07-20 | The Johns Hopkins University | Methods and compositions for treating schizophrenia |
RS63319B1 (sr) | 2015-09-02 | 2022-07-29 | Trevena Inc | Jedinjenja koja modulišu delta-opioidni receptor, koja sadrže 6-člani aza-heterociklik, postupci njihove upotrebe i spravljanja |
KR20190129867A (ko) | 2017-02-17 | 2019-11-20 | 트레베나, 인코포레이티드. | 5-원 아자-헤테로고리 함유 델타-오피오이드 수용체 조절 화합물, 및 그의 사용 및 제조 방법 |
AU2018221705B2 (en) | 2017-02-17 | 2022-10-27 | Trevena, Inc. | 7-membered aza-heterocyclic containing delta-opioid receptor modulating compounds, methods of using and making the same |
WO2020183011A1 (en) | 2019-03-14 | 2020-09-17 | Institut Curie | Htr1d inhibitors and uses thereof in the treatment of cancer |
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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 |
DE69232003T2 (de) | 1991-09-18 | 2002-04-25 | Glaxo Group Ltd | Benzanilidderivate als 5-HT1D-Antagonisten |
EP0765873B1 (en) * | 1991-10-11 | 2002-04-17 | Dupont Pharmaceuticals Company | Cyclic ureas and analogues useful as retroviral protease inhibitors |
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 |
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1997
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- 1997-02-03 KR KR1019980707713A patent/KR100305071B1/ko not_active IP Right Cessation
- 1997-02-03 AU AU13170/97A patent/AU706839B2/en not_active Ceased
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- 1997-02-03 ES ES97900717T patent/ES2246058T3/es not_active Expired - Lifetime
- 1997-02-03 DE DE69733996T patent/DE69733996T2/de not_active Expired - Fee Related
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- 1997-03-25 AR ARP970101200A patent/AR006390A1/es not_active Application Discontinuation
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- 1997-03-26 HR HR60/015,134A patent/HRP970175A2/hr not_active Application Discontinuation
- 1997-03-26 DZ DZ970045A patent/DZ2198A1/fr active
- 1997-03-27 ID IDP971025A patent/ID17781A/id unknown
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- 1997-03-27 ZA ZA972690A patent/ZA972690B/xx unknown
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1998
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1999
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