IL102008A - Quinuclidine derivatives pharmaceutical compositions containing them and uses therof - Google Patents

Quinuclidine derivatives pharmaceutical compositions containing them and uses therof

Info

Publication number: IL102008A
Authority: IL; Israel
Prior art keywords: compound; disorders; substance; formula; methyl
Prior art date: 1991-05-31

Application number

IL10200892A

Other languages

English (en)

Other versions

IL102008A0 (en

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.)

1991-05-31

Filing date

1992-05-26

Publication date

1995-12-08

Family has litigation

First worldwide family litigation filed litigation Critical https://patents.darts-ip.com/?family=24845673&utm_source=google_patent&utm_medium=platform_link&utm_campaign=public_patent_search&patent=IL102008(A) "Global patent litigation dataset” by Darts-ip is licensed under a Creative Commons Attribution 4.0 International License.

1992-05-26 Application filed by Pfizer filed Critical Pfizer

1992-12-30 Publication of IL102008A0 publication Critical patent/IL102008A0/xx

1995-12-08 Publication of IL102008A publication Critical patent/IL102008A/en

Links

239000008194 pharmaceutical composition Substances 0.000 title claims description 13
150000008584 quinuclidines Chemical class 0.000 title description 4
150000001875 compounds Chemical class 0.000 claims abstract description 89
150000003839 salts Chemical class 0.000 claims abstract description 30
208000027866 inflammatory disease Diseases 0.000 claims abstract description 9
208000002193 Pain Diseases 0.000 claims abstract description 8
230000036407 pain Effects 0.000 claims abstract description 8
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims abstract description 3
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims abstract description 3
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims abstract description 3
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 3
125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims abstract description 3
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims abstract description 3
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 55
208000035475 disorder Diseases 0.000 claims description 42
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 36
102100024304 Protachykinin-1 Human genes 0.000 claims description 36
101800003906 Substance P Proteins 0.000 claims description 36
241000124008 Mammalia Species 0.000 claims description 22
239000003814 drug Substances 0.000 claims description 19
230000003042 antagnostic effect Effects 0.000 claims description 14
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206010020751 Hypersensitivity Diseases 0.000 claims description 12
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239000003937 drug carrier Substances 0.000 claims description 10
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VGGMVUWJFXUQBN-YBZGWEFGSA-N (2S,3S)-2-benzhydryl-N-(2-methoxy-5-propan-2-ylphenyl)-2-methyl-1-azabicyclo[2.2.2]octan-3-amine dihydrochloride Chemical compound Cl.Cl.C(C)(C)C=1C=CC(=C(C1)N[C@@H]1[C@@](N2CCC1CC2)(C(C2=CC=CC=C2)C2=CC=CC=C2)C)OC VGGMVUWJFXUQBN-YBZGWEFGSA-N 0.000 claims description 2
UYMNXIGGKXTLHU-VMPREFPWSA-N (2s,3s)-2-benzhydryl-n-(2-methoxy-5-methylphenyl)-2-methyl-1-azabicyclo[2.2.2]octan-3-amine Chemical compound COC1=CC=C(C)C=C1N[C@@H]1[C@@](C(C=2C=CC=CC=2)C=2C=CC=CC=2)(C)N2CCC1CC2 UYMNXIGGKXTLHU-VMPREFPWSA-N 0.000 claims description 2
QFTQKCRAJOXJNK-DKJKITOUSA-N (2s,3s)-2-benzhydryl-n-(5-butan-2-yl-2-methoxyphenyl)-2-methyl-1-azabicyclo[2.2.2]octan-3-amine Chemical compound CCC(C)C1=CC=C(OC)C(N[C@@H]2[C@](N3CCC2CC3)(C)C(C=2C=CC=CC=2)C=2C=CC=CC=2)=C1 QFTQKCRAJOXJNK-DKJKITOUSA-N 0.000 claims description 2
ZXKQLZMZYWXUJC-CDZUIXILSA-N (2s,3s)-2-benzhydryl-n-(5-tert-butyl-2-methoxyphenyl)-2-methyl-1-azabicyclo[2.2.2]octan-3-amine Chemical compound COC1=CC=C(C(C)(C)C)C=C1N[C@@H]1[C@@](C(C=2C=CC=CC=2)C=2C=CC=CC=2)(C)N2CCC1CC2 ZXKQLZMZYWXUJC-CDZUIXILSA-N 0.000 claims description 2
CWWARWOPSKGELM-SARDKLJWSA-N methyl (2s)-2-[[(2s)-2-[[2-[[(2s)-2-[[(2s)-2-[[(2s)-5-amino-2-[[(2s)-5-amino-2-[[(2s)-1-[(2s)-6-amino-2-[[(2s)-1-[(2s)-2-amino-5-(diaminomethylideneamino)pentanoyl]pyrrolidine-2-carbonyl]amino]hexanoyl]pyrrolidine-2-carbonyl]amino]-5-oxopentanoyl]amino]-5 Chemical compound C([C@@H](C(=O)NCC(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCSC)C(=O)OC)NC(=O)[C@H](CC=1C=CC=CC=1)NC(=O)[C@H](CCC(N)=O)NC(=O)[C@H](CCC(N)=O)NC(=O)[C@H]1N(CCC1)C(=O)[C@H](CCCCN)NC(=O)[C@H]1N(CCC1)C(=O)[C@@H](N)CCCN=C(N)N)C1=CC=CC=C1 CWWARWOPSKGELM-SARDKLJWSA-N 0.000 claims description 2
QSBHMJMADHILTB-KYJUHHDHSA-N (2s,3s)-2-benzhydryl-n-(5-ethyl-2-methoxyphenyl)-2-methyl-1-azabicyclo[2.2.2]octan-3-amine Chemical compound CCC1=CC=C(OC)C(N[C@@H]2[C@](N3CCC2CC3)(C)C(C=2C=CC=CC=2)C=2C=CC=CC=2)=C1 QSBHMJMADHILTB-KYJUHHDHSA-N 0.000 claims 1
XPNMCDYOYIKVGB-CONSDPRKSA-N (2s,3s)-2-benzhydryl-n-[(2-methoxy-5-propan-2-ylphenyl)methyl]-1-azabicyclo[2.2.2]octan-3-amine Chemical compound COC1=CC=C(C(C)C)C=C1CN[C@@H]1[C@H](C(C=2C=CC=CC=2)C=2C=CC=CC=2)N2CCC1CC2 XPNMCDYOYIKVGB-CONSDPRKSA-N 0.000 claims 1
OPTAPOYRQUYZJY-UHFFFAOYSA-N CS(=O)(=O)O.CC1(N2CCC(C1N)CC2)C(C2=CC=CC=C2)C2=CC=CC=C2 Chemical compound CS(=O)(=O)O.CC1(N2CCC(C1N)CC2)C(C2=CC=CC=C2)C2=CC=CC=C2 OPTAPOYRQUYZJY-UHFFFAOYSA-N 0.000 claims 1
230000011514 reflex Effects 0.000 claims 1
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239000003890 substance P antagonist Substances 0.000 abstract description 5
208000018522 Gastrointestinal disease Diseases 0.000 abstract description 3
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YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 30
-1 methoxybenzyl group Chemical group 0.000 description 15
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 14
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 13
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
239000000243 solution Substances 0.000 description 11
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 10
238000000034 method Methods 0.000 description 8
239000002585 base Substances 0.000 description 7
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 7
210000001519 tissue Anatomy 0.000 description 7
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 6
DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 6
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
239000003638 chemical reducing agent Substances 0.000 description 6
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239000002253 acid Substances 0.000 description 5
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229910052739 hydrogen Inorganic materials 0.000 description 5
239000001257 hydrogen Substances 0.000 description 5
HQPBPHWHPVDJQU-UHFFFAOYSA-N methanesulfonic acid;octan-3-amine Chemical compound CS(O)(=O)=O.CCCCCC(N)CC HQPBPHWHPVDJQU-UHFFFAOYSA-N 0.000 description 5
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XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
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URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 1
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NLJMYIDDQXHKNR-UHFFFAOYSA-K sodium citrate Chemical compound O.O.[Na+].[Na+].[Na+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O NLJMYIDDQXHKNR-UHFFFAOYSA-K 0.000 description 1
229960001790 sodium citrate Drugs 0.000 description 1
235000011083 sodium citrates Nutrition 0.000 description 1
BEOOHQFXGBMRKU-UHFFFAOYSA-N sodium cyanoborohydride Chemical compound [Na+].[B-]C#N BEOOHQFXGBMRKU-UHFFFAOYSA-N 0.000 description 1
235000019333 sodium laurylsulphate Nutrition 0.000 description 1
239000008247 solid mixture Substances 0.000 description 1
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ADNPLDHMAVUMIW-CUZNLEPHSA-N substance P Chemical compound C([C@@H](C(=O)NCC(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCSC)C(N)=O)NC(=O)[C@H](CC=1C=CC=CC=1)NC(=O)[C@H](CCC(N)=O)NC(=O)[C@H](CCC(N)=O)NC(=O)[C@H]1N(CCC1)C(=O)[C@H](CCCCN)NC(=O)[C@H]1N(CCC1)C(=O)[C@@H](N)CCCN=C(N)N)C1=CC=CC=C1 ADNPLDHMAVUMIW-CUZNLEPHSA-N 0.000 description 1
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Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D453/00—Heterocyclic compounds containing quinuclidine or iso-quinuclidine ring systems, e.g. quinine alkaloids
- C07D453/02—Heterocyclic compounds containing quinuclidine or iso-quinuclidine ring systems, e.g. quinine alkaloids containing not further condensed quinuclidine ring systems
- 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
- A61P1/16—Drugs for disorders of the alimentary tract or the digestive system for liver or gallbladder disorders, e.g. hepatoprotective agents, cholagogues, litholytics
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
- 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
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/04—Centrally acting analgesics, e.g. opioids
- 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
- A61P25/20—Hypnotics; Sedatives
- 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
- A61P25/24—Antidepressants
- 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

Landscapes

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

IL10200892A 1991-05-31 1992-05-26 Quinuclidine derivatives pharmaceutical compositions containing them and uses therof IL102008A (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
US70840491A	1991-05-31	1991-05-31

Publications (2)

Publication Number	Publication Date
IL102008A0 IL102008A0 (en)	1992-12-30
IL102008A true IL102008A (en)	1995-12-08

Family

ID=24845673

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
IL10200892A IL102008A (en)	1991-05-31	1992-05-26	Quinuclidine derivatives pharmaceutical compositions containing them and uses therof

Country Status (41)

Country	Link
US (3)	US5807867A (fr)
EP (1)	EP0587723B1 (fr)
JP (2)	JPH0733386B2 (fr)
KR (1)	KR100214905B1 (fr)
CN (1)	CN1048492C (fr)
AP (1)	AP299A (fr)
AT (1)	ATE135006T1 (fr)
AU (1)	AU657552B2 (fr)
BG (1)	BG61694B1 (fr)
BR (1)	BR9206073A (fr)
CA (1)	CA2102179C (fr)
CZ (1)	CZ281403B6 (fr)
DE (4)	DE122006000066I2 (fr)
DK (1)	DK0587723T3 (fr)
EG (1)	EG19944A (fr)
ES (1)	ES2084361T3 (fr)
FI (1)	FI114475B (fr)
GR (1)	GR3019687T3 (fr)
GT (1)	GT199200028A (fr)
HU (1)	HU217548B (fr)
IE (1)	IE72473B1 (fr)
IL (1)	IL102008A (fr)
IS (1)	IS1611B (fr)
LU (1)	LU91293I2 (fr)
MA (1)	MA22539A1 (fr)
MX (1)	MX9202554A (fr)
NL (1)	NL300250I2 (fr)
NO (2)	NO302701B1 (fr)
NZ (2)	NZ242956A (fr)
OA (1)	OA09867A (fr)
PL (1)	PL171379B1 (fr)
PT (1)	PT100546B (fr)
RO (1)	RO110499B1 (fr)
RU (1)	RU2103269C1 (fr)
SK (1)	SK278788B6 (fr)
TW (1)	TW204349B (fr)
UA (1)	UA27776C2 (fr)
UY (1)	UY23422A1 (fr)
WO (1)	WO1992021677A1 (fr)
YU (1)	YU48995B (fr)
ZA (1)	ZA923942B (fr)

Families Citing this family (88)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
SK278788B6 (sk) *	1991-05-31	1998-02-04	Pfizer Inc.	Chinuklidínové deriváty, spôsob ich prípravy a pou
RU2114848C1 (ru) *	1991-06-20	1998-07-10	Пфайзер Инк.	Фторалкоксибензиламинные производные азотсодержащих гетероциклов, фармацевтическая композиция, способ ингибирования действия вещества р у млекопитающих
DK0655996T3 (da) *	1992-08-19	2001-12-27	Pfizer	Substituerede benzylamino-nitrogenholdige, ikke-aromatiske, heterocykliske forbindelser
KR950704311A (ko) *	1992-11-12	1995-11-17	알렌 제이. 스피겔	물질 p 길항체로서의 퀴누클리딘 유도체(quinuclidine derivative as substance p antagonist)
US5344830A (en) *	1992-12-10	1994-09-06	Merck & Co., Inc.	N,N-diacylpiperazine tachykinin antagonists
JP2822274B2 (ja) *	1993-05-19	1998-11-11	ファイザー製薬株式会社	Ｐ物質拮抗剤としてのヘテロ原子置換アルキルベンジルアミノキヌクリジン類
IL109646A0 (en) *	1993-05-19	1994-08-26	Pfizer	Heteroatom substituted alkyl benzylamino-quinuclidines
US5393762A (en) *	1993-06-04	1995-02-28	Pfizer Inc.	Pharmaceutical agents for treatment of emesis
EP0653208A3 (fr) *	1993-11-17	1995-10-11	Pfizer	Antagonistes de la substance P pour le traitement et la prévention de l'erythème solaire.
EP0659409A3 (fr) *	1993-11-23	1995-08-09	Pfizer	Antagonistes de la substance P pour l'inhibition de l'angiogénése.
EP0655246A1 (fr) *	1993-11-30	1995-05-31	Pfizer Inc.	Antagonistes de la substance P pour le traitement des maladies causées par Helicobacter Pylori ou d'autres bacteries spirales, ureare-positives, gram-négatives
IL116249A (en) *	1994-12-12	2003-07-06	Pfizer	Nk-1 receptor antagonists for the treatment of neuronal damage and stroke
PE8798A1 (es) *	1995-07-17	1998-03-02	Pfizer	Procedimiento de separacion de los enantiomeros del 1-azabiciclo[2.2.2] octan-3-amina, 2-(difenilmetil) -n- [[2-metoxi-5-(1-metiletil) fenil] metil]
TW458774B (en)	1995-10-20	2001-10-11	Pfizer	Antiemetic pharmaceutical compositions
IL123740A0 (en) *	1997-03-28	1998-10-30	Pfizer	NK-1 receptor antagonists for the treatment of delayed emesis
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1992
- 1992-04-28 SK SK3906-92A patent/SK278788B6/sk not_active IP Right Cessation
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- 1992-04-28 HU HU9303393A patent/HU217548B/hu active Protection Beyond IP Right Term
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- 1992-04-28 DK DK92912601.9T patent/DK0587723T3/da active
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Also Published As

Publication number	Publication date
IS3871A (is)	1992-12-02
CZ281403B6 (cs)	1996-09-11
IE72473B1 (en)	1997-04-23
GT199200028A (es)	1993-11-20
BG61694B1 (bg)	1998-03-31
PT100546A (pt)	1993-08-31
NO302701B1 (no)	1998-04-14
CZ390692A3 (en)	1994-02-16
BR9206073A (pt)	1994-12-06
NZ270673A (en)	1997-07-27
NO2007003I2 (no)	2011-04-18
CN1067428A (zh)	1992-12-30
NL300250I1 (nl)	2007-02-01
DE9290063U1 (de)	1994-02-24
YU56492A (sh)	1995-03-27
DE122006000066I1 (de)	2007-03-22
CA2102179C (fr)	1998-10-27
US6222038B1 (en)	2001-04-24
AP299A (en)	1994-01-14
UA27776C2 (uk)	2000-10-16
RU2103269C1 (ru)	1998-01-27
DE69208877T2 (de)	1996-07-25
YU48995B (sh)	2003-04-30
FI935297A0 (fi)	1993-11-29
DE122006000066I2 (de)	2007-12-06
CA2102179A1 (fr)	1992-12-01
LU91293I2 (fr)	2007-02-06
OA09867A (en)	1994-08-15
DK0587723T3 (da)	1996-04-01
JP2645225B2 (ja)	1997-08-25
NO934312L (no)	1993-11-29
HU9303393D0 (en)	1994-03-28
HU217548B (hu)	2000-02-28
KR100214905B1 (ko)	1999-08-02
US5807867A (en)	1998-09-15
NL300250I2 (nl)	2007-03-01
ATE135006T1 (de)	1996-03-15
WO1992021677A1 (fr)	1992-12-10
SK390692A3 (en)	1998-02-04
IE921729A1 (en)	1992-12-02
HUT70151A (en)	1995-09-28
TW204349B (fr)	1993-04-21
ZA923942B (en)	1993-11-29
JPH07285965A (ja)	1995-10-31
JPH06504292A (ja)	1994-05-19
AU657552B2 (en)	1995-03-16
EP0587723B1 (fr)	1996-03-06
SK278788B6 (sk)	1998-02-04
NO934312D0 (no)	1993-11-29
GR3019687T3 (en)	1996-07-31
UY23422A1 (es)	1992-11-12
JPH0733386B2 (ja)	1995-04-12
NO2007003I1 (no)	2007-03-26
CN1048492C (zh)	2000-01-19
FI114475B (fi)	2004-10-29
RO110499B1 (ro)	1996-01-30
MX9202554A (es)	1992-11-01
PT100546B (pt)	1999-12-31
EG19944A (en)	1997-02-27
ES2084361T3 (es)	1996-05-01
FI935297L (fi)	1993-11-29
AU1990192A (en)	1993-01-08
DE69208877D1 (de)	1996-04-11
IS1611B (is)	1996-10-18
PL171379B1 (en)	1997-04-30
EP0587723A1 (fr)	1994-03-23
NZ242956A (en)	1995-06-27
BG98248A (bg)	1994-07-29
US5939433A (en)	1999-08-17
AP9200384A0 (en)	1992-07-31
MA22539A1 (fr)	1992-12-31
IL102008A0 (en)	1992-12-30

Publication	Publication Date	Title
US6222038B1 (en)	2001-04-24	Quinuclidine derivatives
US5886009A (en)	1999-03-23	Quinuclidine derivative as a substance P antagonist
US5688804A (en)	1997-11-18	3-Benzylamino-2-phenyl-piperidine derivatives as substance P receptor antagonists
EP0607164B1 (fr)	2002-05-02	Heterocycles tricycliques fusionnes, contenant de l'azote, utilises comme antagonistes de recepteur de substance p
IL100584A (en)	1995-10-31	1-alkyl-2-benzhydryl-3-arylmethylamino quinuclidinium salts and pharmaceutical compositions containing them
EP0840735B1 (fr)	2003-09-24	Resolution de 1-azabicyclo 2,2,2]octan-3-amine, 2-(diphenylmethyl)-n- 2-methoxy-5-(1-methylethyl)phenyl]methyl]
HK1000246B (en)	1998-02-13	Quinuclidine derivative as substance p antagonist
HK1000246A1 (en)	1998-02-13	Quinuclidine derivative as substance p antagonist

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2010-11-30	NE	Application for restoration - patent lapsed through non-payment of renewal fees (section 60, patents law, 5727-1967)
2011-08-31	PEL	Intention of commissioner to extend period of protection
2012-01-31	EXTG	Extension of patent term granted	Extension date: 20130216
2012-01-31	EXTN	Extension order renewed
2012-12-31	EXTN	Extension order renewed