HRP20010590A2 - Triazole compounds and their use - Google Patents
Triazole compounds and their use Download PDFInfo
- Publication number
- HRP20010590A2 HRP20010590A2 HR20010590A HRP20010590A HRP20010590A2 HR P20010590 A2 HRP20010590 A2 HR P20010590A2 HR 20010590 A HR20010590 A HR 20010590A HR P20010590 A HRP20010590 A HR P20010590A HR P20010590 A2 HRP20010590 A2 HR P20010590A2
- Authority
- HR
- Croatia
- Prior art keywords
- phenyl
- alkyl
- triazol
- propyl
- methyl
- Prior art date
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- -1 Triazole compounds Chemical class 0.000 title claims description 27
- 239000000126 substance Substances 0.000 claims description 91
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 39
- 229910052736 halogen Inorganic materials 0.000 claims description 31
- 150000002367 halogens Chemical class 0.000 claims description 31
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 20
- 238000002360 preparation method Methods 0.000 claims description 19
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 18
- 229910052739 hydrogen Inorganic materials 0.000 claims description 17
- 150000003254 radicals Chemical class 0.000 claims description 16
- 229910052799 carbon Inorganic materials 0.000 claims description 15
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 12
- 125000004432 carbon atom Chemical group C* 0.000 claims description 12
- 229910052757 nitrogen Inorganic materials 0.000 claims description 12
- 229910052760 oxygen Inorganic materials 0.000 claims description 12
- 229910052717 sulfur Inorganic materials 0.000 claims description 12
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 11
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 11
- 125000003396 thiol group Chemical group [H]S* 0.000 claims description 11
- 201000010099 disease Diseases 0.000 claims description 10
- 125000001424 substituent group Chemical group 0.000 claims description 10
- 150000003852 triazoles Chemical class 0.000 claims description 9
- 239000002253 acid Substances 0.000 claims description 8
- 239000003814 drug Substances 0.000 claims description 8
- 125000005842 heteroatom Chemical group 0.000 claims description 8
- 125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims description 6
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 6
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 6
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 6
- 150000003839 salts Chemical class 0.000 claims description 6
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 5
- 125000002373 5 membered heterocyclic group Chemical group 0.000 claims description 4
- JNCMHMUGTWEVOZ-UHFFFAOYSA-N F[CH]F Chemical compound F[CH]F JNCMHMUGTWEVOZ-UHFFFAOYSA-N 0.000 claims description 4
- 108010081348 HRT1 protein Hairy Proteins 0.000 claims description 4
- 102100021881 Hairy/enhancer-of-split related with YRPW motif protein 1 Human genes 0.000 claims description 4
- 150000007513 acids Chemical class 0.000 claims description 4
- 125000003118 aryl group Chemical group 0.000 claims description 4
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 4
- 125000006574 non-aromatic ring group Chemical group 0.000 claims description 4
- 125000001544 thienyl group Chemical group 0.000 claims description 4
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 4
- 125000004429 atom Chemical group 0.000 claims description 3
- 125000002541 furyl group Chemical group 0.000 claims description 3
- 150000002391 heterocyclic compounds Chemical class 0.000 claims description 3
- 125000000623 heterocyclic group Chemical group 0.000 claims description 3
- 125000003373 pyrazinyl group Chemical group 0.000 claims description 3
- 125000004076 pyridyl group Chemical group 0.000 claims description 3
- 125000000168 pyrrolyl group Chemical group 0.000 claims description 3
- 125000000335 thiazolyl group Chemical group 0.000 claims description 3
- PUZSVCVWKDZFCA-UHFFFAOYSA-N 1-[2-[3-[[4-methyl-5-[4-(trifluoromethyl)phenyl]-1,2,4-triazol-3-yl]sulfanyl]propyl]-3,4-dihydro-1h-isoquinolin-7-yl]ethanone Chemical compound C1C2=CC(C(=O)C)=CC=C2CCN1CCCSC(N1C)=NN=C1C1=CC=C(C(F)(F)F)C=C1 PUZSVCVWKDZFCA-UHFFFAOYSA-N 0.000 claims description 2
- 125000004070 6 membered heterocyclic group Chemical group 0.000 claims description 2
- 101100295738 Gallus gallus COR3 gene Proteins 0.000 claims description 2
- 125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 claims description 2
- 125000001624 naphthyl group Chemical group 0.000 claims description 2
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 2
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 2
- 229920006395 saturated elastomer Polymers 0.000 claims description 2
- 125000002827 triflate group Chemical group FC(S(=O)(=O)O*)(F)F 0.000 claims description 2
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 2
- 125000003831 tetrazolyl group Chemical group 0.000 claims 2
- LPXVQPDEFFFPJE-UHFFFAOYSA-N 1-[2-[3-[(4-butyl-5-phenyl-1,2,4-triazol-3-yl)sulfanyl]propyl]-3,4-dihydro-1h-isoquinolin-7-yl]ethanone Chemical compound CCCCN1C(SCCCN2CC3=CC(=CC=C3CC2)C(C)=O)=NN=C1C1=CC=CC=C1 LPXVQPDEFFFPJE-UHFFFAOYSA-N 0.000 claims 1
- FKOHUWDUTYFPRW-UHFFFAOYSA-N 1-[2-[3-[(4-cyclopropyl-5-phenyl-1,2,4-triazol-3-yl)sulfanyl]propyl]-3,4-dihydro-1h-isoquinolin-7-yl]ethanone Chemical compound C1C2=CC(C(=O)C)=CC=C2CCN1CCCSC(N1C2CC2)=NN=C1C1=CC=CC=C1 FKOHUWDUTYFPRW-UHFFFAOYSA-N 0.000 claims 1
- BZZZBOULZLXDPH-UHFFFAOYSA-N 1-[2-[3-[(4-ethyl-5-phenyl-1,2,4-triazol-3-yl)sulfanyl]propyl]-3,4-dihydro-1h-isoquinolin-7-yl]ethanone Chemical compound CCN1C(SCCCN2CC3=CC(=CC=C3CC2)C(C)=O)=NN=C1C1=CC=CC=C1 BZZZBOULZLXDPH-UHFFFAOYSA-N 0.000 claims 1
- RMSHQCVNPVBGQB-UHFFFAOYSA-N 1-[2-[3-[(4-methyl-5-phenyl-1,2,4-triazol-3-yl)sulfanyl]propyl]-3,4-dihydro-1h-isoquinolin-7-yl]ethanone Chemical compound C1C2=CC(C(=O)C)=CC=C2CCN1CCCSC(N1C)=NN=C1C1=CC=CC=C1 RMSHQCVNPVBGQB-UHFFFAOYSA-N 0.000 claims 1
- RDUQOUGAYQZKFB-UHFFFAOYSA-N 1-[2-[3-[(5-phenyl-4-propan-2-yl-1,2,4-triazol-3-yl)sulfanyl]propyl]-3,4-dihydro-1h-isoquinolin-7-yl]ethanone Chemical compound CC(C)N1C(SCCCN2CC3=CC(=CC=C3CC2)C(C)=O)=NN=C1C1=CC=CC=C1 RDUQOUGAYQZKFB-UHFFFAOYSA-N 0.000 claims 1
- IEYHIUSHNYYMEW-UHFFFAOYSA-N 1-[2-[3-[(5-phenyl-4-propyl-1,2,4-triazol-3-yl)sulfanyl]propyl]-3,4-dihydro-1h-isoquinolin-7-yl]ethanone Chemical compound CCCN1C(SCCCN2CC3=CC(=CC=C3CC2)C(C)=O)=NN=C1C1=CC=CC=C1 IEYHIUSHNYYMEW-UHFFFAOYSA-N 0.000 claims 1
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- 229940052760 dopamine agonists Drugs 0.000 claims 1
- 239000000018 receptor agonist Substances 0.000 claims 1
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- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 39
- 238000005160 1H NMR spectroscopy Methods 0.000 description 38
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- 229910000041 hydrogen chloride Inorganic materials 0.000 description 21
- 238000006243 chemical reaction Methods 0.000 description 19
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 18
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 17
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- 239000002904 solvent Substances 0.000 description 13
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- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 12
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 12
- VYFYYTLLBUKUHU-UHFFFAOYSA-N dopamine Chemical compound NCCC1=CC=C(O)C(O)=C1 VYFYYTLLBUKUHU-UHFFFAOYSA-N 0.000 description 12
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- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 8
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- 208000035475 disorder Diseases 0.000 description 8
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- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 6
- QKNYBSVHEMOAJP-UHFFFAOYSA-N 2-amino-2-(hydroxymethyl)propane-1,3-diol;hydron;chloride Chemical compound Cl.OCC(N)(CO)CO QKNYBSVHEMOAJP-UHFFFAOYSA-N 0.000 description 6
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- 102000004073 Dopamine D3 Receptors Human genes 0.000 description 6
- 108090000525 Dopamine D3 Receptors Proteins 0.000 description 6
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 6
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 6
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 6
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 6
- 150000001875 compounds Chemical class 0.000 description 6
- 229960003638 dopamine Drugs 0.000 description 6
- 239000012458 free base Substances 0.000 description 6
- 239000003446 ligand Substances 0.000 description 6
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 6
- 238000000746 purification Methods 0.000 description 6
- XGLHJEZLNGXEAZ-UHFFFAOYSA-N 4-methyl-3-phenyl-1h-1,2,4-triazole-5-thione Chemical compound N1C(=S)N(C)C(C=2C=CC=CC=2)=N1 XGLHJEZLNGXEAZ-UHFFFAOYSA-N 0.000 description 5
- MFESCIUQSIBMSM-UHFFFAOYSA-N I-BCP Chemical compound ClCCCBr MFESCIUQSIBMSM-UHFFFAOYSA-N 0.000 description 5
- 125000000217 alkyl group Chemical group 0.000 description 5
- 239000002585 base Substances 0.000 description 5
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- 238000000605 extraction Methods 0.000 description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 5
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- 150000000565 5-membered heterocyclic compounds Chemical class 0.000 description 2
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- NGQHLYGRTFVUEM-UHFFFAOYSA-N 7-(trifluoromethyl)-1,2,3,4-tetrahydroisoquinoline Chemical compound C1CNCC2=CC(C(F)(F)F)=CC=C21 NGQHLYGRTFVUEM-UHFFFAOYSA-N 0.000 description 2
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
- C07D491/04—Ortho-condensed systems
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Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE19900811 | 1999-01-12 | ||
PCT/EP2000/000177 WO2000042036A1 (de) | 1999-01-12 | 2000-01-12 | Triazolverbindungen mit dopamin-d3-rezeptoraffinität |
Publications (1)
Publication Number | Publication Date |
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HRP20010590A2 true HRP20010590A2 (en) | 2003-08-31 |
Family
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Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
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HR20010590A HRP20010590A2 (en) | 1999-01-12 | 2001-08-10 | Triazole compounds and their use |
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US (3) | US6579892B1 (pt) |
EP (3) | EP1140907B1 (pt) |
JP (3) | JP2002534521A (pt) |
KR (3) | KR100730667B1 (pt) |
CN (3) | CN1267430C (pt) |
AR (3) | AR022229A1 (pt) |
AT (3) | ATE424398T1 (pt) |
AU (3) | AU773047B2 (pt) |
BG (2) | BG65105B1 (pt) |
BR (2) | BR0007500A (pt) |
CA (3) | CA2359948C (pt) |
CO (3) | CO5150227A1 (pt) |
CZ (2) | CZ20012550A3 (pt) |
DE (3) | DE50014472D1 (pt) |
ES (2) | ES2288839T3 (pt) |
HK (1) | HK1045311B (pt) |
HR (1) | HRP20010590A2 (pt) |
HU (2) | HUP0200709A3 (pt) |
ID (2) | ID29930A (pt) |
IL (3) | IL144136A0 (pt) |
NO (2) | NO20013444D0 (pt) |
NZ (2) | NZ512864A (pt) |
PL (2) | PL200238B1 (pt) |
SK (2) | SK9862001A3 (pt) |
TR (2) | TR200102026T2 (pt) |
TW (1) | TWI274750B (pt) |
WO (3) | WO2000042037A1 (pt) |
ZA (2) | ZA200106585B (pt) |
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GB0507680D0 (en) | 2005-04-15 | 2005-05-25 | Glaxo Group Ltd | Compounds |
ATE484502T1 (de) | 2005-06-14 | 2010-10-15 | Glaxo Group Ltd | Neue verbindungen |
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US9227944B2 (en) | 2008-10-10 | 2016-01-05 | Institute Of Pharmacology And Toxicology Academy Of Military Science P.L.A. China | Dopamine D3 receptor ligands and preparation and medical uses of the same |
JP5701213B2 (ja) | 2008-10-10 | 2015-04-15 | インスティチュート オブ ファーマコロジー アンド トキシコロジー アカデミー オブ ミリタリー メディカル サイエンシズ ピー.エル.エー.チャイナ | 新規なドーパミンd3受容体リガンド、その調製及び使用 |
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2000
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- 2000-01-12 TR TR2001/02026T patent/TR200102026T2/xx unknown
- 2000-01-12 CZ CZ20012550A patent/CZ20012550A3/cs unknown
- 2000-01-12 HU HU0200709A patent/HUP0200709A3/hu unknown
- 2000-01-12 EP EP00901535A patent/EP1140907B1/de not_active Expired - Lifetime
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- 2000-01-12 CN CN00804933A patent/CN1347414A/zh active Pending
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2001
- 2001-07-03 IL IL144136A patent/IL144136A/en not_active IP Right Cessation
- 2001-07-11 NO NO20013444A patent/NO20013444D0/no not_active Application Discontinuation
- 2001-07-11 NO NO20013443A patent/NO20013443L/no not_active Application Discontinuation
- 2001-08-03 BG BG105783A patent/BG65105B1/bg unknown
- 2001-08-03 BG BG105784A patent/BG65086B1/bg unknown
- 2001-08-10 HR HR20010590A patent/HRP20010590A2/hr not_active Application Discontinuation
- 2001-08-10 ZA ZA200106585A patent/ZA200106585B/en unknown
- 2001-08-10 ZA ZA200106584A patent/ZA200106584B/en unknown
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2002
- 2002-09-19 HK HK02106847.0A patent/HK1045311B/zh not_active IP Right Cessation
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