SK284802B6 - Deriváty N-triazolylmetylpiperazínu s antagonistickou aktivitou k neurokinínovým receptorom, spôsob ich výroby, medziprodukt a liečivá s ich obsahom - Google Patents

Deriváty N-triazolylmetylpiperazínu s antagonistickou aktivitou k neurokinínovým receptorom, spôsob ich výroby, medziprodukt a liečivá s ich obsahom Download PDF

Info

Publication number: SK284802B6
Authority: SK; Slovakia
Prior art keywords: alkyl; ring; nitrogen; optionally substituted; atoms
Prior art date: 2000-07-28

Application number

SK757-2001A

Other languages

English (en)

Slovak (sk)

Other versions

SK7572001A3 (en

Inventor

Daniel Jasserand

Uwe Sch�N

Holger Sann

Reinhard Br�Ckner

Christian Eeckhout

Original Assignee

Solvay Pharmaceuticals Gmbh

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.)

2000-07-28

Filing date

2001-06-01

Publication date

2005-11-03

2001-06-01 Application filed by Solvay Pharmaceuticals Gmbh filed Critical Solvay Pharmaceuticals Gmbh

2002-02-05 Publication of SK7572001A3 publication Critical patent/SK7572001A3/sk

2005-11-03 Publication of SK284802B6 publication Critical patent/SK284802B6/sk

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FQXWSUOMZGXWNB-UHFFFAOYSA-N 1-(2h-triazol-4-ylmethyl)piperazine Chemical class C=1NN=NC=1CN1CCNCC1 FQXWSUOMZGXWNB-UHFFFAOYSA-N 0.000 title claims abstract description 10
-1 preparation thereof Substances 0.000 title claims description 24
238000002360 preparation method Methods 0.000 title claims description 16
239000003814 drug Substances 0.000 title claims description 6
239000013067 intermediate product Substances 0.000 title abstract 2
239000002464 receptor antagonist Substances 0.000 title 1
229940044551 receptor antagonist Drugs 0.000 title 1
150000001875 compounds Chemical class 0.000 claims abstract description 154
238000000034 method Methods 0.000 claims abstract description 33
230000008569 process Effects 0.000 claims abstract description 12
125000000217 alkyl group Chemical group 0.000 claims description 126
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 76
229910052757 nitrogen Inorganic materials 0.000 claims description 47
125000006413 ring segment Chemical group 0.000 claims description 36
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 31
GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims description 30
125000003545 alkoxy group Chemical group 0.000 claims description 30
150000003839 salts Chemical class 0.000 claims description 23
229910052739 hydrogen Inorganic materials 0.000 claims description 21
238000006243 chemical reaction Methods 0.000 claims description 20
239000001257 hydrogen Substances 0.000 claims description 20
125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 18
229910052736 halogen Inorganic materials 0.000 claims description 18
150000002367 halogens Chemical class 0.000 claims description 18
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 18
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 18
239000002253 acid Substances 0.000 claims description 17
YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 16
125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 16
QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 16
125000002837 carbocyclic group Chemical group 0.000 claims description 15
125000006239 protecting group Chemical group 0.000 claims description 15
229910052799 carbon Inorganic materials 0.000 claims description 14
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 12
125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims description 12
229910052717 sulfur Inorganic materials 0.000 claims description 12
239000011593 sulfur Substances 0.000 claims description 12
125000000980 1H-indol-3-ylmethyl group Chemical group [H]C1=C([H])C([H])=C2N([H])C([H])=C(C([H])([H])[*])C2=C1[H] 0.000 claims description 11
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 11
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 11
239000001301 oxygen Substances 0.000 claims description 11
229910052760 oxygen Inorganic materials 0.000 claims description 11
125000004430 oxygen atom Chemical group O* 0.000 claims description 11
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 10
125000004432 carbon atom Chemical group C* 0.000 claims description 9
150000002431 hydrogen Chemical class 0.000 claims description 9
125000003282 alkyl amino group Chemical group 0.000 claims description 8
RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical group C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 7
125000004429 atom Chemical group 0.000 claims description 7
239000000546 pharmaceutical excipient Substances 0.000 claims description 6
125000004122 cyclic group Chemical group 0.000 claims description 5
125000005842 heteroatom Chemical group 0.000 claims description 5
NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 4
125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 4
125000001064 morpholinomethyl group Chemical group [H]C([H])(*)N1C([H])([H])C([H])([H])OC([H])([H])C1([H])[H] 0.000 claims description 4
125000004193 piperazinyl group Chemical group 0.000 claims description 4
125000004434 sulfur atom Chemical group 0.000 claims description 4
QPMLSUSACCOBDK-UHFFFAOYSA-N diazepane Chemical compound C1CCNNCC1 QPMLSUSACCOBDK-UHFFFAOYSA-N 0.000 claims description 2
150000003235 pyrrolidines Chemical group 0.000 claims description 2
125000004183 alkoxy alkyl group Chemical group 0.000 claims 3
125000001359 1,2,3-triazol-4-yl group Chemical group [H]N1N=NC([*])=C1[H] 0.000 claims 1
125000005078 alkoxycarbonylalkyl group Chemical group 0.000 claims 1
239000003937 drug carrier Substances 0.000 claims 1
125000004404 heteroalkyl group Chemical group 0.000 claims 1
229940124531 pharmaceutical excipient Drugs 0.000 claims 1
108050000302 Neurokinin receptors Proteins 0.000 abstract description 8
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XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 48
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OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 27
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ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 17
BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 16
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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 description 8
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 8
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 8
102100024304 Protachykinin-1 Human genes 0.000 description 8
101800003906 Substance P Proteins 0.000 description 8
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 8
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 8
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 7
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230000036772 blood pressure Effects 0.000 description 7
239000002775 capsule Substances 0.000 description 7
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 7
150000004885 piperazines Chemical group 0.000 description 7
150000003335 secondary amines Chemical group 0.000 description 7
125000001424 substituent group Chemical group 0.000 description 7
239000000725 suspension Substances 0.000 description 7
238000001308 synthesis method Methods 0.000 description 7
GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Chemical compound OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 6
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
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RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 5
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 5
102100021260 Galactosylgalactosylxylosylprotein 3-beta-glucuronosyltransferase 1 Human genes 0.000 description 5
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101000600903 Homo sapiens Substance-P receptor Proteins 0.000 description 5
MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 5
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125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 5
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RCHDLEVSZBOHOS-UHFFFAOYSA-N 1,4-dichlorobut-2-yne Chemical compound ClCC#CCCl RCHDLEVSZBOHOS-UHFFFAOYSA-N 0.000 description 4
ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 4
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 4
PXIPVTKHYLBLMZ-UHFFFAOYSA-N Sodium azide Chemical compound [Na+].[N-]=[N+]=[N-] PXIPVTKHYLBLMZ-UHFFFAOYSA-N 0.000 description 4
150000001412 amines Chemical class 0.000 description 4
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ZOWMTYKIOFIWJW-UHFFFAOYSA-N 2-(piperazin-2-ylmethyl)-1h-indole Chemical class C=1C2=CC=CC=C2NC=1CC1CNCCN1 ZOWMTYKIOFIWJW-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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125000001399 1,2,3-triazolyl group Chemical group N1N=NC(=C1)* 0.000 description 2
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AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
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Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero rings
- 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
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/04—Drugs for disorders of the alimentary tract or the digestive system for ulcers, gastritis or reflux esophagitis, e.g. antacids, inhibitors of acid secretion, mucosal protectants
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/06—Anti-spasmodics, e.g. drugs for colics, esophagic dyskinesia
- 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
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
- 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
- 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
- C07D403/14—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 three or more hetero rings

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Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
Public Health (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Chemical Kinetics & Catalysis (AREA)
Pharmacology & Pharmacy (AREA)
Veterinary Medicine (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Bioinformatics & Cheminformatics (AREA)
Engineering & Computer Science (AREA)
Biomedical Technology (AREA)
Neurology (AREA)
Neurosurgery (AREA)
Pain & Pain Management (AREA)
Rheumatology (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)
Plural Heterocyclic Compounds (AREA)

SK757-2001A 2000-07-28 2001-06-01 Deriváty N-triazolylmetylpiperazínu s antagonistickou aktivitou k neurokinínovým receptorom, spôsob ich výroby, medziprodukt a liečivá s ich obsahom SK284802B6 (sk)

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DE10036818A DE10036818A1 (de)	2000-07-28	2000-07-28	Neue N-Triazolylmethyl-Piperazinderivate als Neurokininrezeptor-Antagonisten

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SK284802B6 true SK284802B6 (sk)	2005-11-03

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US (1)	US6407106B1 (ja)
EP (1)	EP1176144B1 (ja)
JP (1)	JP2002053577A (ja)
KR (1)	KR100924405B1 (ja)
CN (1)	CN1167698C (ja)
AR (1)	AR028743A1 (ja)
AT (1)	ATE244716T1 (ja)
AU (1)	AU779318B2 (ja)
BR (1)	BR0103048A (ja)
CA (1)	CA2354213C (ja)
CZ (1)	CZ301695B6 (ja)
DE (2)	DE10036818A1 (ja)
DK (1)	DK1176144T3 (ja)
DZ (1)	DZ3119A1 (ja)
ES (1)	ES2201007T3 (ja)
HU (1)	HU226687B1 (ja)
IL (1)	IL144299A (ja)
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NO (1)	NO323233B1 (ja)
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PL (1)	PL210436B1 (ja)
PT (1)	PT1176144E (ja)
RU (1)	RU2288918C2 (ja)
SK (1)	SK284802B6 (ja)
TW (1)	TWI304403B (ja)
UA (1)	UA73728C2 (ja)
ZA (1)	ZA200105737B (ja)

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UA77515C2 (en) *	2002-04-04	2006-12-15		Diazabicyclo alkane derivatives possessing neuroldnin-nk1 receptor antagonistic activity
WO2003091227A1 (en) *	2002-04-26	2003-11-06	Eli Lilly And Company	Tachykinin receptor antagonists
AR039329A1 (es) *	2002-04-26	2005-02-16	Lilly Co Eli	Derivados de triazol, antagonistas de receptor de taquicinina
EP1638944A1 (en) *	2003-06-12	2006-03-29	Eli Lilly And Company	Tachykinin receptor antagonists
US20070082905A1 (en) *	2005-05-27	2007-04-12	De Vries Michiel H	Pharmaceutical compositions comprising n-triazolymethyl-piperazine compounds and methods of using same
EP1910316B1 (en) *	2005-07-25	2010-11-10	F. Hoffmann-La Roche AG	Substituted triazole derivatives and their use as neurokinin 3 receptor antagonists
PE20081229A1 (es) *	2006-12-01	2008-08-28	Merck & Co Inc	Antagonistas de receptor de orexina de diazepam sustituido
KR20090112722A (ko)	2007-01-24	2009-10-28	글락소 그룹 리미티드	3,5-디아미노-6-(2,3-디클로로페닐)-1,2,4-트리아진 또는 ｒ(-)-2,4-디아미노-5-(2,3-디클로로페닐)-6-플루오로메틸 피리미딘 및 ｎｋ1을 포함하는 제약 조성물
EP2467159A1 (en)	2009-08-20	2012-06-27	INSERM (Institut National de la Santé et de la Recherche Médicale)	Vla-4 as a biomarker for prognosis and target for therapy in duchenne muscular dystrophy
EP2729147B1 (en)	2011-07-04	2017-09-06	IRBM - Science Park S.p.A.	Nk-1 receptor antagonists for treating corneal neovascularisation
US20210015834A1 (en)	2018-02-26	2021-01-21	Ospedale San Raffaele S.R.L.	Nk-1 antagonists for use in the treatment of ocular pain
WO2021180885A1 (en)	2020-03-11	2021-09-16	Ospedale San Raffaele S.R.L.	Treatment of stem cell deficiency
CN115184498B (zh) *	2022-07-15	2023-02-21	山东京卫制药有限公司	N-Boc-哌嗪中有关物质哌嗪的检测方法

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IL111730A (en) *	1993-11-29	1998-12-06	Fujisawa Pharmaceutical Co	Piperazine derivatives processes for the preparation thereof and pharmaceutical compositions containing the same
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GB9513118D0 (en) *	1995-06-28	1995-08-30	Merck Sharp & Dohme	Therapeutic agents
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DE19824865A1 (de) *	1997-08-27	1999-03-04	Solvay Pharm Gmbh	Neue Harnstoffderivate
ES2162731B1 (es) *	1999-06-04	2003-02-16	Faes Fabrica Espanola De Produ	Nuevas arilpiperacilnilalquil-3(2h)-piridacinonas.

2000
- 2000-07-28 DE DE10036818A patent/DE10036818A1/de not_active Withdrawn
2001
- 2001-05-23 CZ CZ20011813A patent/CZ301695B6/cs not_active IP Right Cessation
- 2001-06-01 SK SK757-2001A patent/SK284802B6/sk not_active IP Right Cessation
- 2001-06-21 AR ARP010102959A patent/AR028743A1/es active IP Right Grant
- 2001-07-10 CN CNB011228261A patent/CN1167698C/zh not_active Expired - Fee Related
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- 2001-07-12 TW TW090117136A patent/TWI304403B/zh not_active IP Right Cessation
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- 2001-07-19 DK DK01117433T patent/DK1176144T3/da active
- 2001-07-19 PT PT01117433T patent/PT1176144E/pt unknown
- 2001-07-19 AT AT01117433T patent/ATE244716T1/de active
- 2001-07-19 EP EP01117433A patent/EP1176144B1/de not_active Expired - Lifetime
- 2001-07-19 DE DE50100358T patent/DE50100358D1/de not_active Expired - Lifetime
- 2001-07-25 JP JP2001224792A patent/JP2002053577A/ja active Pending
- 2001-07-26 AU AU57675/01A patent/AU779318B2/en not_active Ceased
- 2001-07-26 BR BR0103048-5A patent/BR0103048A/pt not_active IP Right Cessation
- 2001-07-26 CA CA2354213A patent/CA2354213C/en not_active Expired - Fee Related
- 2001-07-27 US US09/915,558 patent/US6407106B1/en not_active Expired - Lifetime
- 2001-07-27 PL PL348946A patent/PL210436B1/pl not_active IP Right Cessation
- 2001-07-27 UA UA2001075403A patent/UA73728C2/uk unknown
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Also Published As

Publication number	Publication date
DE10036818A1 (de)	2002-02-07
CZ20011813A3 (cs)	2002-03-13
SK7572001A3 (en)	2002-02-05
RU2288918C2 (ru)	2006-12-10
CN1167698C (zh)	2004-09-22
US20020065276A1 (en)	2002-05-30
NO20013709D0 (no)	2001-07-27
CN1335316A (zh)	2002-02-13
PL210436B1 (pl)	2012-01-31
EP1176144B1 (de)	2003-07-09
EP1176144A1 (de)	2002-01-30
ES2201007T3 (es)	2004-03-16
TWI304403B (en)	2008-12-21
IL144299A0 (en)	2002-05-23
AU779318B2 (en)	2005-01-13
CA2354213C (en)	2010-04-27
UA73728C2 (en)	2005-09-15
HUP0102931A3 (en)	2003-07-28
HU226687B1 (en)	2009-06-29
NO323233B1 (no)	2007-02-05
AU5767501A (en)	2002-01-31
DE50100358D1 (de)	2003-08-14
HUP0102931A2 (hu)	2002-11-28
US6407106B1 (en)	2002-06-18
CZ301695B6 (cs)	2010-05-26
KR100924405B1 (ko)	2009-10-29
JP2002053577A (ja)	2002-02-19
PL348946A1 (en)	2002-02-11
PT1176144E (pt)	2003-11-28
IL144299A (en)	2004-08-31
DK1176144T3 (da)	2003-10-27
BR0103048A (pt)	2002-04-02
KR20020010482A (ko)	2002-02-04
NZ513041A (en)	2002-12-20
HK1042699A1 (en)	2002-08-23
NO20013709L (no)	2002-01-29
DZ3119A1 (fr)	2004-09-19
AR028743A1 (es)	2003-05-21
ZA200105737B (en)	2002-01-22
HU0102931D0 (en)	2001-09-28
ATE244716T1 (de)	2003-07-15
CA2354213A1 (en)	2002-01-28
IN191021B (ja)	2003-09-13

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2013-03-01	MM4A	Patent lapsed due to non-payment of maintenance fees	Effective date: 20120601