UA62966C2 - Quaternary ammonuim compounds as tachykinin antagonists - Google Patents

Quaternary ammonuim compounds as tachykinin antagonists Download PDF

Info

Publication number: UA62966C2
Authority: UA; Ukraine
Prior art keywords: phenyl; dichlorophenyl; disease; compound; group
Prior art date: 1997-06-18

Application number

UA99126551A

Other languages

English (en)

Ukrainian (uk)

Original Assignee

Pfizer

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.)

1997-06-18

Filing date

1998-05-06

Publication date

2004-01-15

1998-05-06 Application filed by Pfizer filed Critical Pfizer

2004-01-15 Publication of UA62966C2 publication Critical patent/UA62966C2/uk

Links

150000001875 compounds Chemical class 0.000 title claims abstract description 140
239000005557 antagonist Substances 0.000 title abstract description 7
102000003141 Tachykinin Human genes 0.000 title abstract description 4
108060008037 tachykinin Proteins 0.000 title abstract description 4
-1 2,3-dihydrobenzo[b]furanyl Chemical group 0.000 claims abstract description 99
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 69
125000001153 fluoro group Chemical group F* 0.000 claims abstract description 18
150000001450 anions Chemical class 0.000 claims abstract description 16
125000001424 substituent group Chemical group 0.000 claims abstract description 16
125000001072 heteroaryl group Chemical group 0.000 claims abstract description 13
125000001624 naphthyl group Chemical group 0.000 claims abstract description 10
125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 9
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims abstract description 8
125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims abstract description 8
125000004432 carbon atom Chemical group C* 0.000 claims abstract description 7
125000001544 thienyl group Chemical group 0.000 claims abstract description 7
229910052799 carbon Inorganic materials 0.000 claims abstract description 5
125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims abstract description 5
VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims abstract description 3
239000005977 Ethylene Substances 0.000 claims abstract description 3
125000002947 alkylene group Chemical group 0.000 claims abstract description 3
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims abstract description 3
125000001041 indolyl group Chemical group 0.000 claims abstract description 3
125000004076 pyridyl group Chemical group 0.000 claims abstract description 3
125000000753 cycloalkyl group Chemical group 0.000 claims abstract 6
239000000203 mixture Substances 0.000 claims description 142
238000000034 method Methods 0.000 claims description 41
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 38
201000010099 disease Diseases 0.000 claims description 27
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims description 23
125000000217 alkyl group Chemical group 0.000 claims description 17
241000282414 Homo sapiens Species 0.000 claims description 14
230000003042 antagnostic effect Effects 0.000 claims description 14
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 14
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims description 13
125000004204 2-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C(OC([H])([H])[H])C([H])=C1[H] 0.000 claims description 12
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 12
102000007124 Tachykinin Receptors Human genes 0.000 claims description 12
108010072901 Tachykinin Receptors Proteins 0.000 claims description 12
208000035475 disorder Diseases 0.000 claims description 11
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 11
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210000003169 central nervous system Anatomy 0.000 claims description 10
150000002367 halogens Chemical class 0.000 claims description 10
125000001622 2-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C(*)C([H])=C([H])C2=C1[H] 0.000 claims description 9
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 9
239000000460 chlorine Substances 0.000 claims description 9
229910052801 chlorine Inorganic materials 0.000 claims description 9
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 9
229910052736 halogen Inorganic materials 0.000 claims description 9
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PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 8
229910052731 fluorine Inorganic materials 0.000 claims description 8
239000011737 fluorine Substances 0.000 claims description 8
230000002496 gastric effect Effects 0.000 claims description 8
201000004624 Dermatitis Diseases 0.000 claims description 7
125000003545 alkoxy group Chemical group 0.000 claims description 7
125000002541 furyl group Chemical group 0.000 claims description 7
208000006673 asthma Diseases 0.000 claims description 6
125000004189 3,4-dichlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(Cl)C([H])=C1* 0.000 claims description 5
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206010011224 Cough Diseases 0.000 claims description 5
208000011231 Crohn disease Diseases 0.000 claims description 5
206010012289 Dementia Diseases 0.000 claims description 5
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208000019693 Lung disease Diseases 0.000 claims description 5
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241000208225 Rhus Species 0.000 claims description 5
235000014220 Rhus chinensis Nutrition 0.000 claims description 5
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206010003246 arthritis Diseases 0.000 claims description 5
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206010009887 colitis Diseases 0.000 claims description 5
208000014439 complex regional pain syndrome type 2 Diseases 0.000 claims description 5
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239000012634 fragment Substances 0.000 claims description 5
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230000035859 hyperreflexia Effects 0.000 claims description 5
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125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 5
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WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 4
206010012438 Dermatitis atopic Diseases 0.000 claims description 4
206010036376 Postherpetic Neuralgia Diseases 0.000 claims description 4
201000008937 atopic dermatitis Diseases 0.000 claims description 4
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 4
229910052794 bromium Inorganic materials 0.000 claims description 4
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 4
125000006239 protecting group Chemical group 0.000 claims description 4
OVFCSRJZUQAXOA-UHFFFAOYSA-N 1-azoniabicyclo[2.2.2]octane;methanesulfonate Chemical compound CS([O-])(=O)=O.C1CC2CC[NH+]1CC2 OVFCSRJZUQAXOA-UHFFFAOYSA-N 0.000 claims description 3
206010039085 Rhinitis allergic Diseases 0.000 claims description 3
201000010105 allergic rhinitis Diseases 0.000 claims description 3
125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 3
229940126601 medicinal product Drugs 0.000 claims description 3
125000005948 methanesulfonyloxy group Chemical group 0.000 claims description 3
125000005951 trifluoromethanesulfonyloxy group Chemical group 0.000 claims description 3
125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 3
125000004201 2,4-dichlorophenyl group Chemical group [H]C1=C([H])C(*)=C(Cl)C([H])=C1Cl 0.000 claims description 2
125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 claims description 2
CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 claims description 2
229910002651 NO3 Inorganic materials 0.000 claims description 2
NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 claims description 2
QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 claims description 2
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 2
239000013543 active substance Substances 0.000 claims description 2
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 2
229940077388 benzenesulfonate Drugs 0.000 claims description 2
SRSXLGNVWSONIS-UHFFFAOYSA-M benzenesulfonate Chemical compound [O-]S(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-M 0.000 claims description 2
125000004122 cyclic group Chemical group 0.000 claims description 2
239000003085 diluting agent Substances 0.000 claims description 2
230000003993 interaction Effects 0.000 claims description 2
PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 claims description 2
239000001301 oxygen Substances 0.000 claims description 2
229910052760 oxygen Inorganic materials 0.000 claims description 2
239000008194 pharmaceutical composition Substances 0.000 claims description 2
229910052709 silver Inorganic materials 0.000 claims description 2
125000001712 tetrahydronaphthyl group Chemical group C1(CCCC2=CC=CC=C12)* 0.000 claims description 2
JOXIMZWYDAKGHI-UHFFFAOYSA-M toluene-4-sulfonate Chemical compound CC1=CC=C(S([O-])(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-M 0.000 claims description 2
208000023783 Genitourinary tract disease Diseases 0.000 claims 2
GRVDJDISBSALJP-UHFFFAOYSA-N methyloxidanyl Chemical compound [O]C GRVDJDISBSALJP-UHFFFAOYSA-N 0.000 claims 2
241000588653 Neisseria Species 0.000 claims 1
SZMUSGRLLRWRIV-UHFFFAOYSA-N [4-methoxy-3-propan-2-yloxy-2-(trifluoromethoxy)phenyl] hypofluorite Chemical compound COC1=C(C(=C(OF)C=C1)OC(F)(F)F)OC(C)C SZMUSGRLLRWRIV-UHFFFAOYSA-N 0.000 claims 1
JFSPBVWPKOEZCB-UHFFFAOYSA-N fenfuram Chemical compound O1C=CC(C(=O)NC=2C=CC=CC=2)=C1C JFSPBVWPKOEZCB-UHFFFAOYSA-N 0.000 claims 1
125000000229 (C1-C4)alkoxy group Chemical group 0.000 abstract description 7
125000005843 halogen group Chemical group 0.000 abstract description 4
125000004169 (C1-C6) alkyl group Chemical group 0.000 abstract description 3
125000002252 acyl group Chemical group 0.000 abstract description 2
125000004178 (C1-C4) alkyl group Chemical group 0.000 abstract 7
125000002861 (C1-C4) alkanoyl group Chemical group 0.000 abstract 1
125000004453 alkoxycarbonyl group Chemical group 0.000 abstract 1
125000003016 chromanyl group Chemical group O1C(CCC2=CC=CC=C12)* 0.000 abstract 1
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 243
238000002360 preparation method Methods 0.000 description 157
230000002829 reductive effect Effects 0.000 description 113
239000002904 solvent Substances 0.000 description 111
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 105
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 96
238000005481 NMR spectroscopy Methods 0.000 description 74
239000000243 solution Substances 0.000 description 72
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 69
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238000004587 chromatography analysis Methods 0.000 description 26
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Vascular Medicine (AREA)
Orthopedic Medicine & Surgery (AREA)
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Molecular Biology (AREA)
Ophthalmology & Optometry (AREA)
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UA99126551A 1997-06-18 1998-05-06 Quaternary ammonuim compounds as tachykinin antagonists UA62966C2 (en)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
GBGB9712882.1A GB9712882D0 (en)	1997-06-18	1997-06-18	Quaternary ammonium compounds
PCT/EP1998/003500 WO1998057972A1 (fr)	1997-06-18	1998-06-05	Composes d'ammonium quaternaire utiles en tant qu'antagonistes des tachykinines

Publications (1)

Publication Number	Publication Date
UA62966C2 true UA62966C2 (en)	2004-01-15

Family

ID=10814535

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
UA99126551A UA62966C2 (en)	1997-06-18	1998-05-06	Quaternary ammonuim compounds as tachykinin antagonists

Country Status (43)

Country	Link
US (2)	US6207678B1 (fr)
EP (1)	EP0994876B1 (fr)
JP (1)	JP3280993B2 (fr)
KR (1)	KR100345389B1 (fr)
CN (1)	CN1199971C (fr)
AP (1)	AP947A (fr)
AR (1)	AR012249A1 (fr)
AT (1)	ATE275564T1 (fr)
AU (1)	AU726027B2 (fr)
BG (1)	BG63341B1 (fr)
BR (1)	BR9810619A (fr)
CA (1)	CA2291975C (fr)
CO (1)	CO4940478A1 (fr)
DE (1)	DE69826129T2 (fr)
DZ (1)	DZ2524A1 (fr)
EA (1)	EA002424B1 (fr)
ES (1)	ES2227856T3 (fr)
GB (1)	GB9712882D0 (fr)
HN (1)	HN1998000087A (fr)
HR (1)	HRP980337B1 (fr)
HU (1)	HUP0003962A3 (fr)
ID (1)	ID23410A (fr)
IL (2)	IL155621A0 (fr)
IS (1)	IS5269A (fr)
MA (1)	MA26509A1 (fr)
MY (1)	MY136376A (fr)
NO (1)	NO995782L (fr)
NZ (1)	NZ501286A (fr)
OA (1)	OA11235A (fr)
PA (1)	PA8452501A1 (fr)
PE (1)	PE80099A1 (fr)
PL (1)	PL189557B1 (fr)
PT (1)	PT994876E (fr)
SI (1)	SI0994876T1 (fr)
SK (1)	SK283346B6 (fr)
TN (1)	TNSN98089A1 (fr)
TR (1)	TR199903135T2 (fr)
TW (1)	TW479055B (fr)
UA (1)	UA62966C2 (fr)
UY (1)	UY25045A1 (fr)
WO (1)	WO1998057972A1 (fr)
YU (1)	YU64699A (fr)
ZA (1)	ZA985239B (fr)

Families Citing this family (8)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
EP1043031A4 (fr) *	1997-12-26	2007-05-02	Astellas Pharma Inc	Compositions medicinales a liberation prolongee
JP4546589B2 (ja) *	1998-04-23	2010-09-15	武田薬品工業株式会社	ナフタレン誘導体
WO2001095904A1 (fr) *	2000-06-12	2001-12-20	University Of Rochester	Methode de traitement de symptomes de la variation hormonale, tels que les bouffees de chaleur, au moyen d'un antagoniste du recepteur de la tachykinine
AU2002230665A1 (en) *	2000-12-06	2002-06-18	Sepracor, Inc.	4,4-disubstituted piperidines for use as dopamine, serotonin and norepinephrine ligands
EP1556054A4 (fr) *	2002-05-29	2007-09-05	Univ California	Antagonisation de recepteurs nk-1 inhibant la toxicomanie
WO2004091597A2 (fr) *	2003-04-15	2004-10-28	Pharmacia & Upjohn Company Llc	Procede pour traiter le syndrome du colon irritable
JP2007536270A (ja) *	2004-05-07	2007-12-13	ジヤンセン・フアーマシユーチカ・ナームローゼ・フエンノートシヤツプ	イミダゾール誘導体のスケールアップ可能な合成
WO2008090114A1 (fr)	2007-01-24	2008-07-31	Glaxo Group Limited	Compositions pharmaceutiques contenant du 2-méthoxy-5- (5-trifluorométhyl-tétrazol-i-yl-benzyl) - (2s-phényl-pipéridin-3s-yl-)

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US3991201A (en) *	1974-06-27	1976-11-09	Janssen Pharmaceutica N.V.	1-(β-Aryl-β-R-ethyl)imidazoles as antimicrobial agents
FR2696178B1 (fr) *	1992-09-30	1994-12-30	Sanofi Elf	Amides basiques quaternaires, procédé pour leur préparation et compositions pharmaceutiques en contenant.
US5583134A (en) *	1992-09-30	1996-12-10	Sanofi	1-azoniabicyclo[2.2.2] octanes and pharmaceutical compositions in which they are present

1997
- 1997-06-18 GB GBGB9712882.1A patent/GB9712882D0/en active Pending
1998
- 1998-05-06 UA UA99126551A patent/UA62966C2/uk unknown
- 1998-05-19 TW TW087107720A patent/TW479055B/zh not_active IP Right Cessation
- 1998-06-04 PA PA19988452501A patent/PA8452501A1/es unknown
- 1998-06-04 HN HN1998000087A patent/HN1998000087A/es unknown
- 1998-06-05 US US09/380,370 patent/US6207678B1/en not_active Expired - Fee Related
- 1998-06-05 KR KR1019997011931A patent/KR100345389B1/ko not_active Expired - Fee Related
- 1998-06-05 CA CA002291975A patent/CA2291975C/fr not_active Expired - Fee Related
- 1998-06-05 SK SK1744-99A patent/SK283346B6/sk unknown
- 1998-06-05 DE DE69826129T patent/DE69826129T2/de not_active Expired - Fee Related
- 1998-06-05 PL PL98337713A patent/PL189557B1/pl not_active IP Right Cessation
- 1998-06-05 HU HU0003962A patent/HUP0003962A3/hu unknown
- 1998-06-05 SI SI9830692T patent/SI0994876T1/xx unknown
- 1998-06-05 CN CNB988063425A patent/CN1199971C/zh not_active Expired - Fee Related
- 1998-06-05 TR TR1999/03135T patent/TR199903135T2/xx unknown
- 1998-06-05 JP JP50368799A patent/JP3280993B2/ja not_active Expired - Fee Related
- 1998-06-05 AT AT98932148T patent/ATE275564T1/de not_active IP Right Cessation
- 1998-06-05 PT PT98932148T patent/PT994876E/pt unknown
- 1998-06-05 EP EP98932148A patent/EP0994876B1/fr not_active Expired - Lifetime
- 1998-06-05 ID IDW991633A patent/ID23410A/id unknown
- 1998-06-05 ES ES98932148T patent/ES2227856T3/es not_active Expired - Lifetime
- 1998-06-05 BR BR9810619-8A patent/BR9810619A/pt not_active Application Discontinuation
- 1998-06-05 IL IL15562198A patent/IL155621A0/xx not_active IP Right Cessation
- 1998-06-05 YU YU64699A patent/YU64699A/sh unknown
- 1998-06-05 AU AU82153/98A patent/AU726027B2/en not_active Ceased
- 1998-06-05 NZ NZ501286A patent/NZ501286A/xx unknown
- 1998-06-05 IL IL13307998A patent/IL133079A/en not_active IP Right Cessation
- 1998-06-05 EA EA199900986A patent/EA002424B1/ru not_active IP Right Cessation
- 1998-06-05 WO PCT/EP1998/003500 patent/WO1998057972A1/fr not_active Ceased
- 1998-06-08 PE PE1998000468A patent/PE80099A1/es not_active Application Discontinuation
- 1998-06-11 AP APAP/P/1998/001262A patent/AP947A/en active
- 1998-06-15 UY UY25045A patent/UY25045A1/es unknown
- 1998-06-16 MY MYPI98002689A patent/MY136376A/en unknown
- 1998-06-16 AR ARP980102853A patent/AR012249A1/es active IP Right Grant
- 1998-06-17 ZA ZA9805239A patent/ZA985239B/xx unknown
- 1998-06-17 TN TNTNSN98089A patent/TNSN98089A1/fr unknown
- 1998-06-17 DZ DZ980134A patent/DZ2524A1/fr active
- 1998-06-17 MA MA25118A patent/MA26509A1/fr unknown
- 1998-06-18 HR HR980337A patent/HRP980337B1/xx not_active IP Right Cessation
- 1998-06-18 CO CO98034807A patent/CO4940478A1/es unknown
1999
- 1999-11-23 BG BG103919A patent/BG63341B1/bg unknown
- 1999-11-23 IS IS5269A patent/IS5269A/is unknown
- 1999-11-25 NO NO995782A patent/NO995782L/no not_active Application Discontinuation
- 1999-12-15 OA OA9900281A patent/OA11235A/en unknown
2000
- 2000-12-11 US US09/734,266 patent/US6380396B1/en not_active Expired - Fee Related

Also Published As

Publication number	Publication date
IL155621A0 (en)	2003-11-23
CA2291975A1 (fr)	1998-12-23
NO995782D0 (no)	1999-11-25
AU726027B2 (en)	2000-10-26
ZA985239B (en)	1999-12-17
IL133079A0 (en)	2001-03-19
SK283346B6 (sk)	2003-06-03
OA11235A (en)	2003-07-09
TW479055B (en)	2002-03-11
NO995782L (no)	2000-02-16
IS5269A (is)	1999-11-23
YU64699A (sh)	2002-06-19
PL189557B1 (pl)	2005-08-31
DE69826129D1 (de)	2004-10-14
PL337713A1 (en)	2000-08-28
ID23410A (id)	2000-04-20
EP0994876A1 (fr)	2000-04-26
JP2000513030A (ja)	2000-10-03
JP3280993B2 (ja)	2002-05-13
NZ501286A (en)	2000-07-28
AU8215398A (en)	1999-01-04
TR199903135T2 (xx)	2000-04-21
CN1199971C (zh)	2005-05-04
HUP0003962A2 (hu)	2001-04-28
BG63341B1 (bg)	2001-10-31
BR9810619A (pt)	2000-09-12
CA2291975C (fr)	2004-02-10
AR012249A1 (es)	2000-09-27
SI0994876T1 (en)	2005-02-28
HRP980337B1 (en)	2003-02-28
PT994876E (pt)	2005-01-31
TNSN98089A1 (fr)	2005-03-15
GB9712882D0 (en)	1997-08-20
PA8452501A1 (es)	2000-05-24
BG103919A (en)	2001-07-31
MY136376A (en)	2008-09-30
AP947A (en)	2001-03-08
SK174499A3 (en)	2001-05-10
EA199900986A1 (ru)	2000-06-26
KR20010013909A (ko)	2001-02-26
US6207678B1 (en)	2001-03-27
ES2227856T3 (es)	2005-04-01
KR100345389B1 (ko)	2002-07-24
PE80099A1 (es)	1999-08-25
EA002424B1 (ru)	2002-04-25
EP0994876B1 (fr)	2004-09-08
DZ2524A1 (fr)	2003-02-01
IL133079A (en)	2004-06-01
ATE275564T1 (de)	2004-09-15
CN1260795A (zh)	2000-07-19
MA26509A1 (fr)	2004-12-20
UY25045A1 (es)	2000-09-29
CO4940478A1 (es)	2000-07-24
HRP980337A2 (en)	1999-02-28
HN1998000087A (es)	1998-10-22
WO1998057972A1 (fr)	1998-12-23
AP9801262A0 (en)	1998-06-30
DE69826129T2 (de)	2005-09-22
HUP0003962A3 (en)	2001-12-28
US6380396B1 (en)	2002-04-30

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NO311977B1 (no)	2002-02-25	(Azetidin-1-ylalkyl) laktamer som tachykinin-antagonister
RU2158264C2 (ru)	2000-10-27	3-азетидинилалкилпиперидины или пирролидины в качестве антагонистов тахикинина, способы их получения, промежуточные соединения, фармацевтическая композиция на их основе и способ лечения
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US20050176772A1 (en)	2005-08-11	Pharmaceutically active compounds
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