ZA200202589B - Chemical compounds. - Google Patents

Chemical compounds. Download PDF

Info

Publication number: ZA200202589B
Authority: ZA; South Africa
Prior art keywords: methyl; group; phenyl; compound; hydrogen
Prior art date: 1999-10-07

Application number

ZA200202589A

Other languages

English (en)

Inventor

Giuseppe Alvaro

Romano Di Fabio

Riccardo Giovannini

Giuseppe Guercio

Yves St-Denis

Antonella Ursini

Original Assignee

Glaxo Group Ltd

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1999-10-07

Filing date

2002-04-03

Publication date

2003-08-27

2002-04-03 Application filed by Glaxo Group Ltd filed Critical Glaxo Group Ltd

2003-08-27 Publication of ZA200202589B publication Critical patent/ZA200202589B/en

Links

150000001875 compounds Chemical class 0.000 title claims description 93
239000001257 hydrogen Substances 0.000 claims description 57
229910052739 hydrogen Inorganic materials 0.000 claims description 57
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 37
125000000217 alkyl group Chemical group 0.000 claims description 35
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 34
-1 hydroxy, amino, methylamino, dimethylamino Chemical group 0.000 claims description 29
238000011282 treatment Methods 0.000 claims description 26
125000004432 carbon atom Chemical group C* 0.000 claims description 17
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical group N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 16
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 15
150000003839 salts Chemical class 0.000 claims description 14
QDZOEBFLNHCSSF-PFFBOGFISA-N (2S)-2-[[(2R)-2-[[(2S)-1-[(2S)-6-amino-2-[[(2S)-1-[(2R)-2-amino-5-carbamimidamidopentanoyl]pyrrolidine-2-carbonyl]amino]hexanoyl]pyrrolidine-2-carbonyl]amino]-3-(1H-indol-3-yl)propanoyl]amino]-N-[(2R)-1-[[(2S)-1-[[(2R)-1-[[(2S)-1-[[(2S)-1-amino-4-methyl-1-oxopentan-2-yl]amino]-4-methyl-1-oxopentan-2-yl]amino]-3-(1H-indol-3-yl)-1-oxopropan-2-yl]amino]-1-oxo-3-phenylpropan-2-yl]amino]-3-(1H-indol-3-yl)-1-oxopropan-2-yl]pentanediamide Chemical compound C([C@@H](C(=O)N[C@H](CC=1C2=CC=CC=C2NC=1)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CC(C)C)C(N)=O)NC(=O)[C@@H](CC=1C2=CC=CC=C2NC=1)NC(=O)[C@H](CCC(N)=O)NC(=O)[C@@H](CC=1C2=CC=CC=C2NC=1)NC(=O)[C@H]1N(CCC1)C(=O)[C@H](CCCCN)NC(=O)[C@H]1N(CCC1)C(=O)[C@H](N)CCCNC(N)=N)C1=CC=CC=C1 QDZOEBFLNHCSSF-PFFBOGFISA-N 0.000 claims description 11
102100024304 Protachykinin-1 Human genes 0.000 claims description 10
101800003906 Substance P Proteins 0.000 claims description 10
239000002253 acid Substances 0.000 claims description 10
229910052799 carbon Chemical group 0.000 claims description 10
125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 10
229910052736 halogen Inorganic materials 0.000 claims description 10
150000002367 halogens Chemical class 0.000 claims description 10
239000000203 mixture Substances 0.000 claims description 10
239000012453 solvate Substances 0.000 claims description 10
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 10
238000002360 preparation method Methods 0.000 claims description 9
238000000034 method Methods 0.000 claims description 8
229910052757 nitrogen Inorganic materials 0.000 claims description 8
239000003814 drug Substances 0.000 claims description 7
229910052731 fluorine Inorganic materials 0.000 claims description 7
239000011737 fluorine Substances 0.000 claims description 7
102000003141 Tachykinin Human genes 0.000 claims description 6
125000000753 cycloalkyl group Chemical group 0.000 claims description 6
125000005843 halogen group Chemical group 0.000 claims description 6
239000008194 pharmaceutical composition Substances 0.000 claims description 6
108060008037 tachykinin Proteins 0.000 claims description 6
125000006569 (C5-C6) heterocyclic group Chemical group 0.000 claims description 5
125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 5
125000003545 alkoxy group Chemical group 0.000 claims description 5
238000006243 chemical reaction Methods 0.000 claims description 5
230000001404 mediated effect Effects 0.000 claims description 5
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 5
125000003342 alkenyl group Chemical group 0.000 claims description 4
125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 4
230000008569 process Effects 0.000 claims description 4
125000000022 2-aminoethyl group Chemical group [H]C([*])([H])C([H])([H])N([H])[H] 0.000 claims description 3
125000006164 6-membered heteroaryl group Chemical group 0.000 claims description 3
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims description 3
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 3
239000005864 Sulphur Chemical group 0.000 claims description 3
150000001412 amines Chemical class 0.000 claims description 3
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 3
125000003630 glycyl group Chemical group [H]N([H])C([H])([H])C(*)=O 0.000 claims description 3
125000005842 heteroatom Chemical group 0.000 claims description 3
125000004433 nitrogen atom Chemical group N* 0.000 claims description 3
QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 3
239000001301 oxygen Substances 0.000 claims description 3
229910052760 oxygen Inorganic materials 0.000 claims description 3
239000000546 pharmaceutical excipient Substances 0.000 claims description 3
125000004193 piperazinyl group Chemical group 0.000 claims description 3
230000009467 reduction Effects 0.000 claims description 3
125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 3
125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 2
RXWMPRIHXVRKNM-UHFFFAOYSA-N 2-phenylpiperazine-1-carboxylic acid Chemical compound OC(=O)N1CCNCC1C1=CC=CC=C1 RXWMPRIHXVRKNM-UHFFFAOYSA-N 0.000 claims description 2
125000006163 5-membered heteroaryl group Chemical group 0.000 claims description 2
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 2
125000001153 fluoro group Chemical group F* 0.000 claims description 2
150000007530 organic bases Chemical class 0.000 claims description 2
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
125000006239 protecting group Chemical group 0.000 claims description 2
125000001424 substituent group Chemical group 0.000 claims description 2
238000002560 therapeutic procedure Methods 0.000 claims description 2
UCPYLLCMEDAXFR-UHFFFAOYSA-N triphosgene Chemical compound ClC(Cl)(Cl)OC(=O)OC(Cl)(Cl)Cl UCPYLLCMEDAXFR-UHFFFAOYSA-N 0.000 claims description 2
150000002431 hydrogen Chemical class 0.000 claims 11
125000002887 hydroxy group Chemical group [H]O* 0.000 claims 2
VNVQBRRPWZODEL-UHFFFAOYSA-N 2-(3,4-dichlorophenyl)piperazine-1-carboxylic acid Chemical compound OC(=O)N1CCNCC1C1=CC=C(Cl)C(Cl)=C1 VNVQBRRPWZODEL-UHFFFAOYSA-N 0.000 claims 1
NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims 1
RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims 1
SGPGESCZOCHFCL-UHFFFAOYSA-N Tilisolol hydrochloride Chemical compound [Cl-].C1=CC=C2C(=O)N(C)C=C(OCC(O)C[NH2+]C(C)(C)C)C2=C1 SGPGESCZOCHFCL-UHFFFAOYSA-N 0.000 claims 1
239000000969 carrier Substances 0.000 claims 1
238000002955 isolation Methods 0.000 claims 1
125000006178 methyl benzyl group Chemical group 0.000 claims 1
238000000926 separation method Methods 0.000 claims 1
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
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RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
241000282414 Homo sapiens Species 0.000 description 4
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JTJMJGYZQZDUJJ-UHFFFAOYSA-N phencyclidine Chemical compound C1CCCCN1C1(C=2C=CC=CC=2)CCCCC1 JTJMJGYZQZDUJJ-UHFFFAOYSA-N 0.000 description 4
229950010883 phencyclidine Drugs 0.000 description 4
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125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 description 3
PRPHSPRYBLISIU-UHFFFAOYSA-N 2-(4-fluoro-2-methylphenyl)piperazine-1-carboxylic acid Chemical compound CC1=CC(F)=CC=C1C1N(C(O)=O)CCNC1 PRPHSPRYBLISIU-UHFFFAOYSA-N 0.000 description 3
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ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
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- 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
- C07D241/04—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/06—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms

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ZA200202589A 1999-10-07 2002-04-03 Chemical compounds. ZA200202589B (en)

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GBGB9923748.9A GB9923748D0 (en)	1999-10-07	1999-10-07	Chemical compounds

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US (6)	US6951861B1 (el)
EP (3)	EP1460066B1 (el)
JP (1)	JP4776844B2 (el)
KR (2)	KR100857671B1 (el)
CN (1)	CN100413850C (el)
AR (2)	AR025975A1 (el)
AT (3)	ATE407125T1 (el)
AU (1)	AU768780B2 (el)
BR (1)	BR0014541A (el)
CA (1)	CA2386515C (el)
CO (1)	CO5251467A1 (el)
CY (2)	CY1110172T1 (el)
CZ (1)	CZ302340B6 (el)
DE (3)	DE60012031T2 (el)
DK (3)	DK1218359T3 (el)
ES (3)	ES2329130T3 (el)
GB (1)	GB9923748D0 (el)
HK (3)	HK1052506B (el)
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IL (2)	IL148964A0 (el)
MX (1)	MXPA02003515A (el)
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NZ (2)	NZ531127A (el)
PE (1)	PE20010741A1 (el)
PL (1)	PL201191B1 (el)
PT (3)	PT1454901E (el)
SI (3)	SI1454901T1 (el)
TN (1)	TNSN00194A1 (el)
TR (1)	TR200200936T2 (el)
TW (1)	TWI225485B (el)
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ZA (1)	ZA200202589B (el)

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1999
- 1999-10-07 GB GBGB9923748.9A patent/GB9923748D0/en not_active Ceased
2000
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- 2000-10-05 AT AT04076650T patent/ATE407125T1/de active
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2002
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Publication number	Publication date
KR20020038800A (ko)	2002-05-23
EP1454901B1 (en)	2008-09-03
CA2386515A1 (en)	2001-04-12
BR0014541A (pt)	2002-09-17
TNSN00194A1 (en)	2005-11-10
AR025975A1 (es)	2002-12-26
IL148964A (en)	2007-02-11
ES2329130T3 (es)	2009-11-23
PL356261A1 (en)	2004-06-28
PT1454901E (pt)	2008-12-12
DE60042501D1 (de)	2009-08-13
US7345041B2 (en)	2008-03-18
CN1391564A (zh)	2003-01-15
US7071196B2 (en)	2006-07-04
PL201191B1 (pl)	2009-03-31
JP2003511377A (ja)	2003-03-25
HK1065798A1 (en)	2005-03-04
ATE270664T1 (de)	2004-07-15
CN100413850C (zh)	2008-08-27
ATE407125T1 (de)	2008-09-15
CZ302340B6 (cs)	2011-03-23
EP1454901A1 (en)	2004-09-08
DE60040176D1 (de)	2008-10-16
ES2312917T3 (es)	2009-03-01
PE20010741A1 (es)	2001-07-18
TWI225485B (en)	2004-12-21
MXPA02003515A (es)	2002-09-02
DK1454901T3 (da)	2009-01-12
US20060122192A1 (en)	2006-06-08
KR100817373B1 (ko)	2008-03-27
HK1066537A1 (en)	2005-03-24
EP1218359B1 (en)	2004-07-07
NZ518144A (en)	2004-04-30
WO2001025219A3 (en)	2001-12-13
US20040209893A1 (en)	2004-10-21
EP1460066B1 (en)	2009-07-01
NO20021637D0 (no)	2002-04-05
SI1218359T1 (en)	2005-02-28
SI1460066T1 (sl)	2009-12-31
ES2222927T3 (es)	2005-02-16
NO20021637L (no)	2002-06-06
KR20070112308A (ko)	2007-11-22
IL148964A0 (en)	2002-11-10
PT1218359E (pt)	2004-10-29
AR077414A2 (es)	2011-08-24
ATE435215T1 (de)	2009-07-15
DK1218359T3 (da)	2004-10-18
KR100857671B1 (ko)	2008-09-08
EP1218359A2 (en)	2002-07-03
MY130907A (en)	2007-07-31
AU7913900A (en)	2001-05-10
CZ20021166A3 (cs)	2002-11-13
DK1460066T3 (da)	2009-11-02
JP4776844B2 (ja)	2011-09-21
US7625904B2 (en)	2009-12-01
CY1110172T1 (el)	2015-01-14
CA2386515C (en)	2011-06-07
TR200200936T2 (tr)	2002-07-22
NO323776B1 (no)	2007-07-02
SI1454901T1 (sl)	2009-02-28
US20080249108A1 (en)	2008-10-09
US6642240B2 (en)	2003-11-04
HK1052506A1 (en)	2003-09-19
US20030028021A1 (en)	2003-02-06
HUP0203136A3 (en)	2003-03-28
CO5251467A1 (es)	2003-02-28
DE60012031T2 (de)	2005-07-07
US20040048862A1 (en)	2004-03-11
EP1460066A1 (en)	2004-09-22
GB9923748D0 (en)	1999-12-08
PT1460066E (pt)	2009-09-10
WO2001025219A2 (en)	2001-04-12
CY1110104T1 (el)	2015-01-14
HUP0203136A2 (hu)	2003-02-28
AU768780B2 (en)	2004-01-08
DE60012031D1 (de)	2004-08-12
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US6951861B1 (en)	2005-10-04

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EP1326832B1 (en)	2004-10-06	Chemical compounds
AU2001295723A1 (en)	2002-07-04	Chemical compounds
ZA200404842B (en)	2005-09-28	Piperidine derivatives
EP1472243A1 (en)	2004-11-03	Piperidine derivatives and their use as antagonists of tachykinins
EP1377558B1 (en)	2005-08-17	[1,4]-diazepane-1-carboxylic acid derivatives, process for their preparation and their use as tachykinin antagonists
US20080249132A1 (en)	2008-10-09	Piperidine Carboxyamide Derivate Suitable as Tachykinin Receptor Antagonist
USRE39921E1 (en)	2007-11-13	Chemical compounds
WO2007009777A1 (en)	2007-01-25	Chemical compounds
WO2007009758A2 (en)	2007-01-25	2r,4s) -4- (4-acetyl-3-hydroxy-1-piperazinyl) -n- { (1r) -1- [3, 5-bis (trifluoromethyl) phenyl] ethyl} -2- (4-fluoro-2-methylphenyl) -n-methyl-1-piperidine-carboxamide as tachykinin receptor antagonist