OA11236A - Azetidinylpropylpiperidine derivatives intermediates and use as tachykinin antagonists - Google Patents

Azetidinylpropylpiperidine derivatives intermediates and use as tachykinin antagonists Download PDF

Info

Publication number: OA11236A
Authority: OA; OAPI
Prior art keywords: halogen; optionally substituted; compound; alkyl; disease
Prior art date: 1997-07-04

Application number

OA9900282A

Other languages

English (en)

Inventor

David Alker

Thomas Victor Magee

Graham Nigel Maw

Donald Stuart Middleton

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.)

1997-07-04

Filing date

1999-12-15

Publication date

2003-05-27

1999-12-15 Application filed by Pfizer filed Critical Pfizer

2003-05-27 Publication of OA11236A publication Critical patent/OA11236A/en

Links

102000003141 Tachykinin Human genes 0.000 title claims abstract description 9
108060008037 tachykinin Proteins 0.000 title claims abstract description 9
239000005557 antagonist Substances 0.000 title claims description 8
239000000543 intermediate Substances 0.000 title description 8
IHOZTRFPYRXIIN-UHFFFAOYSA-N 1-[3-(azetidin-1-yl)propyl]piperidine Chemical class C1CCCCN1CCCN1CCC1 IHOZTRFPYRXIIN-UHFFFAOYSA-N 0.000 title description 4
150000001875 compounds Chemical class 0.000 claims abstract description 164
229910052736 halogen Inorganic materials 0.000 claims abstract description 98
150000002367 halogens Chemical class 0.000 claims abstract description 96
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 35
125000001424 substituent group Chemical group 0.000 claims abstract description 25
150000003839 salts Chemical class 0.000 claims abstract description 24
125000001153 fluoro group Chemical group F* 0.000 claims abstract description 22
125000003118 aryl group Chemical group 0.000 claims abstract description 12
125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims abstract description 7
CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical group O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 claims abstract description 7
108010040722 Neurokinin-2 Receptors Proteins 0.000 claims abstract description 7
102100029409 Neuromedin-K receptor Human genes 0.000 claims abstract description 7
101001125071 Homo sapiens Neuromedin-K receptor Proteins 0.000 claims abstract description 6
125000005073 adamantyl group Chemical group C12(CC3CC(CC(C1)C3)C2)* 0.000 claims abstract description 5
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims abstract description 5
102100037342 Substance-K receptor Human genes 0.000 claims abstract description 4
125000000217 alkyl group Chemical group 0.000 claims description 96
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 84
NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 59
239000000203 mixture Substances 0.000 claims description 55
238000000034 method Methods 0.000 claims description 47
208000035475 disorder Diseases 0.000 claims description 45
201000010099 disease Diseases 0.000 claims description 39
238000006243 chemical reaction Methods 0.000 claims description 31
125000000753 cycloalkyl group Chemical group 0.000 claims description 30
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125000001309 chloro group Chemical group Cl* 0.000 claims description 4
208000027866 inflammatory disease Diseases 0.000 claims description 4
230000004054 inflammatory process Effects 0.000 claims description 4
QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 4
125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 claims description 4
230000003612 virological effect Effects 0.000 claims description 4
206010003645 Atopy Diseases 0.000 claims description 3
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PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 3
125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 claims description 3
239000003085 diluting agent Substances 0.000 claims description 3
210000002950 fibroblast Anatomy 0.000 claims description 3
239000011737 fluorine Substances 0.000 claims description 3
229910052731 fluorine Inorganic materials 0.000 claims description 3
230000002981 neuropathic effect Effects 0.000 claims description 3
230000000392 somatic effect Effects 0.000 claims description 3
125000004189 3,4-dichlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(Cl)C([H])=C1* 0.000 claims description 2
125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 claims description 2
102000008186 Collagen Human genes 0.000 claims description 2
108010035532 Collagen Proteins 0.000 claims description 2
208000027771 Obstructive airways disease Diseases 0.000 claims description 2
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 2
229920001436 collagen Polymers 0.000 claims description 2
125000004188 dichlorophenyl group Chemical group 0.000 claims description 2
125000001072 heteroaryl group Chemical group 0.000 claims description 2
125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims description 2
239000008194 pharmaceutical composition Substances 0.000 claims description 2
208000011580 syndromic disease Diseases 0.000 claims description 2
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 2
125000001544 thienyl group Chemical group 0.000 claims description 2
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 9
125000004566 azetidin-1-yl group Chemical group N1(CCC1)* 0.000 claims 2
JYQQWQJCEUMXQZ-UHFFFAOYSA-N methyl cyanate Chemical compound COC#N JYQQWQJCEUMXQZ-UHFFFAOYSA-N 0.000 claims 2
ICQSKAQXLPIUOE-UHFFFAOYSA-N 3-(3,4-dichlorophenyl)piperidine Chemical compound C1=C(Cl)C(Cl)=CC=C1C1CNCCC1 ICQSKAQXLPIUOE-UHFFFAOYSA-N 0.000 claims 1
YLDCUKJMEKGGFI-QCSRICIXSA-N 4-acetamidobenzoic acid;9-[(2r,3r,4s,5r)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-3h-purin-6-one;1-(dimethylamino)propan-2-ol Chemical compound CC(O)CN(C)C.CC(O)CN(C)C.CC(O)CN(C)C.CC(=O)NC1=CC=C(C(O)=O)C=C1.CC(=O)NC1=CC=C(C(O)=O)C=C1.CC(=O)NC1=CC=C(C(O)=O)C=C1.O[C@@H]1[C@H](O)[C@@H](CO)O[C@H]1N1C(NC=NC2=O)=C2N=C1 YLDCUKJMEKGGFI-QCSRICIXSA-N 0.000 claims 1
108010040716 Neurokinin-3 Receptors Proteins 0.000 claims 1
239000002671 adjuvant Substances 0.000 claims 1
150000001412 amines Chemical class 0.000 claims 1
238000006268 reductive amination reaction Methods 0.000 claims 1
125000004169 (C1-C6) alkyl group Chemical group 0.000 abstract 4
125000004178 (C1-C4) alkyl group Chemical group 0.000 abstract 3
125000000229 (C1-C4)alkoxy group Chemical group 0.000 abstract 2
125000004191 (C1-C6) alkoxy group Chemical group 0.000 abstract 1
108010040718 Neurokinin-1 Receptors Proteins 0.000 abstract 1
102000002002 Neurokinin-1 Receptors Human genes 0.000 abstract 1
239000003112 inhibitor Substances 0.000 abstract 1
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 220
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 175
238000002360 preparation method Methods 0.000 description 54
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 52
239000000243 solution Substances 0.000 description 51
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 39
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 36
238000005481 NMR spectroscopy Methods 0.000 description 34
VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 29
239000000908 ammonium hydroxide Substances 0.000 description 29
235000011114 ammonium hydroxide Nutrition 0.000 description 29
229940043379 ammonium hydroxide Drugs 0.000 description 29
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 25
238000004809 thin layer chromatography Methods 0.000 description 25
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 22
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 21
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 20
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VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 15
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IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 14
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WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
239000012044 organic layer Substances 0.000 description 8
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HEAUFJZALFKPBA-YRVBCFNBSA-N Neurokinin A Chemical compound C([C@@H](C(=O)N[C@H](C(=O)NCC(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCSC)C(N)=O)C(C)C)NC(=O)[C@H](CO)NC(=O)[C@H](CC(O)=O)NC(=O)[C@@H](NC(=O)[C@H](CCCCN)NC(=O)[C@@H](N)CC=1NC=NC=1)C(C)O)C1=CC=CC=C1 HEAUFJZALFKPBA-YRVBCFNBSA-N 0.000 description 7
238000007796 conventional method Methods 0.000 description 7
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NXJCBFBQEVOTOW-UHFFFAOYSA-L palladium(2+);dihydroxide Chemical compound O[Pd]O NXJCBFBQEVOTOW-UHFFFAOYSA-L 0.000 description 7
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HONIICLYMWZJFZ-UHFFFAOYSA-N azetidine Chemical compound C1CNC1 HONIICLYMWZJFZ-UHFFFAOYSA-N 0.000 description 6
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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
- C07D401/02—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 two hetero rings
- C07D401/06—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 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
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- A—HUMAN NECESSITIES
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- A61P13/00—Drugs for disorders of the urinary system
- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
- 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
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/04—Antibacterial agents
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/12—Antivirals
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/08—Antiallergic agents
- 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
- C07D205/00—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom
- C07D205/02—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings
- C07D205/04—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom 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
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D211/08—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms
- C07D211/18—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D211/20—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms with hydrocarbon radicals, substituted by singly bound oxygen or sulphur atoms
- C07D211/22—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms with hydrocarbon radicals, substituted by singly bound oxygen or sulphur atoms by oxygen atoms
- 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
- C07D403/04—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 directly linked by a ring-member-to-ring-member bond

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OA9900282A 1997-07-04 1999-12-15 Azetidinylpropylpiperidine derivatives intermediates and use as tachykinin antagonists OA11236A (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
GBGB9714129.5A GB9714129D0 (en)	1997-07-04	1997-07-04	Azetidines

Publications (1)

Publication Number	Publication Date
OA11236A true OA11236A (en)	2003-05-27

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OA9900282A OA11236A (en)	1997-07-04	1999-12-15	Azetidinylpropylpiperidine derivatives intermediates and use as tachykinin antagonists

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US (1)	US6262046B1 (is)
EP (1)	EP1023285A1 (is)
JP (1)	JP2000511207A (is)
KR (1)	KR20010015532A (is)
CN (1)	CN1261887A (is)
AP (1)	AP1110A (is)
AR (1)	AR013171A1 (is)
AU (1)	AU726708B2 (is)
BG (1)	BG103992A (is)
BR (1)	BR9810544A (is)
CA (1)	CA2294193A1 (is)
CO (1)	CO4950604A1 (is)
DZ (1)	DZ2550A1 (is)
EA (1)	EA002773B1 (is)
GB (1)	GB9714129D0 (is)
GT (1)	GT199800106A (is)
HN (1)	HN1998003689A (is)
HR (1)	HRP20000002B1 (is)
HU (1)	HUP0002330A3 (is)
ID (1)	ID24090A (is)
IL (1)	IL133433A0 (is)
IS (1)	IS5295A (is)
MA (1)	MA26519A1 (is)
NO (1)	NO996115L (is)
NZ (1)	NZ501715A (is)
OA (1)	OA11236A (is)
PA (1)	PA8454601A1 (is)
PE (1)	PE83999A1 (is)
PL (1)	PL338004A1 (is)
SK (1)	SK182799A3 (is)
TN (1)	TNSN98127A1 (is)
TR (1)	TR200000025T2 (is)
TW (1)	TW492960B (is)
UY (1)	UY25079A1 (is)
WO (1)	WO1999001451A1 (is)
ZA (1)	ZA985875B (is)

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GB9714129D0 (en)	1997-07-04	1997-09-10	Pfizer Ltd	Azetidines
AU1089599A (en) *	1997-10-15	1999-05-03	Coelacanth Chemical Corporation	Synthesis of azetidine derivatives
FR2787449B3 (fr)	1998-12-15	2001-01-12	Sanofi Sa	Derives de 3-phenyl-2,6-dioxopiperidin-3-yl propionamide et leur procede de preparation
FR2787448B3 (fr)	1998-12-18	2001-01-12	Sanofi Sa	Ester d'alkyle inferieur de l'acide 3-(3,4-dihalogenophenyl) -2,6-dioxopiperidine3-propionique et son mode de preparation
FR2805817B1 (fr) *	2000-03-03	2002-04-26	Aventis Pharma Sa	Compositions pharmaceutiques contenant des derives d'azetidine, les nouveaux derives d'azetidine et leur preparation
FR2805810B1 (fr) *	2000-03-03	2002-04-26	Aventis Pharma Sa	Compositions pharmaceutiques contenant des derives de 3- amino-azetidine, les nouveaux derives et leur preparation
US6566356B2 (en)	2000-03-03	2003-05-20	Aventis Pharma S.A.	Pharmaceutical compositions containing 3-aminoazetidine derivatives, novel derivatives and their preparation
CA2509406C (en) *	2002-12-23	2012-07-03	Janssen Pharmaceutica N.V.	Substituted 1-piperidin-4-yl-4-azetidin-3-yl-piperazine derivatives and their use as neurokinin antagonists
TW200508221A (en)	2003-06-13	2005-03-01	Astrazeneca Ab	New azetidine compounds
FR2876689B1 (fr) *	2004-10-14	2008-02-22	Aventis Pharma Sa	Nouveau procede et intermediaires de preparation de derives de n-(1-benzhydryl-azetidin-3-yl)-n-phenyl-methylsulfonamide
TW200630337A (en)	2004-10-14	2006-09-01	Euro Celtique Sa	Piperidinyl compounds and the use thereof
NZ556628A (en) *	2005-03-08	2009-09-25	Janssen Pharmaceutica Nv	Diaza-spiro-[4.4]-nonane derivatives as neurokinin (NK1) antagonists
WO2007110449A1 (en) *	2006-03-29	2007-10-04	Euro-Celtique S.A.	Benzenesulfonamide compounds and their use
WO2007118853A1 (en) *	2006-04-13	2007-10-25	Euro-Celtique S.A.	Benzenesulfonamide compounds and their use as blockers of calcium channels
TW200812963A (en) *	2006-04-13	2008-03-16	Euro Celtique Sa	Benzenesulfonamide compounds and the use thereof
US8106208B2 (en)	2006-05-18	2012-01-31	Albireo Ab	Benzamide compounds that act as NK receptor antagonists
US8093268B2 (en)	2007-01-24	2012-01-10	Glaxo Group Limited	Pharmaceutical compositions comprising 2-methoxy-5-(5-trifluoromethyl-tetrazol-1-yl-benzyl)-(2S-phenylpiperidin-3S-yl-)
WO2008124118A1 (en) *	2007-04-09	2008-10-16	Purdue Pharma L.P.	Benzenesulfonyl compounds and the use therof
JP2010535733A (ja)	2007-08-07	2010-11-25	エフ．ホフマン−ラロシュアーゲー	Ｎｋ３受容体アンタゴニストとしてのピロリジンアリールエーテル
WO2009040659A2 (en)	2007-09-28	2009-04-02	Purdue Pharma L.P.	Benzenesulfonamide compounds and the use thereof
CA2988707C (en)	2015-06-16	2023-10-10	Eisai R&D Management Co., Ltd.	Combination of cbp/catenin inhibitor and immune checkpoint inhibitor for treating cancer
KR102559211B1 (ko)	2015-06-23	2023-07-25	에자이 알앤드디 매니지먼트 가부시키가이샤	(6S,9aS)-N-벤질-8-({6-[3-(4-에틸피페라진-1-일)아제티딘-1-일]피리딘-2-일}메틸)-6-(2-플루오로-4-하이드록시벤질)-4,7-디옥소-2-(프로프-2-엔-1-일)헥사하이드로-2H-피라지노[2,1-c][1,2,4]트리아진-1(6H)-카복사마이드의 결정
CN110072528B (zh)	2017-02-08	2022-04-26	卫材R&D管理有限公司	治疗肿瘤的药物组合物
WO2018212202A1 (en)	2017-05-16	2018-11-22	Eisai R&D Management Co., Ltd.	Treatment of hepatocellular carcinoma

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FR2676055B1 (fr) *	1991-05-03	1993-09-03	Sanofi Elf	Composes polycycliques amines et leurs enantiomeres, procede pour leur preparation et compositions pharmaceutiques les contenant.
US5625060A (en)	1991-05-03	1997-04-29	Elf Sanofi	Polycyclic amine compounds and their enantiomers, their method of preparation and pharmaceutical compositions on which they are present
TW432061B (en)	1994-08-09	2001-05-01	Pfizer Res & Dev	Lactams
FR2729951B1 (fr) *	1995-01-30	1997-04-18	Sanofi Sa	Nouveaux composes heterocycliques, procede pour leur preparation et compositions pharmaceutiques en contenant
GB9600235D0 (en)	1996-01-05	1996-03-06	Pfizer Ltd	Therapeutic agents
GB9601697D0 (en) *	1996-01-27	1996-03-27	Pfizer Ltd	Therapeutic agents
GB9714129D0 (en)	1997-07-04	1997-09-10	Pfizer Ltd	Azetidines

1997
- 1997-07-04 GB GBGB9714129.5A patent/GB9714129D0/en active Pending
1998
- 1998-06-01 TW TW087108533A patent/TW492960B/zh active
- 1998-06-30 HN HN1998003689A patent/HN1998003689A/es unknown
- 1998-07-01 JP JP11506382A patent/JP2000511207A/ja active Pending
- 1998-07-01 NZ NZ501715A patent/NZ501715A/en unknown
- 1998-07-01 MA MA25151A patent/MA26519A1/fr unknown
- 1998-07-01 WO PCT/EP1998/004177 patent/WO1999001451A1/en not_active Ceased
- 1998-07-01 CA CA002294193A patent/CA2294193A1/en not_active Abandoned
- 1998-07-01 DZ DZ980160A patent/DZ2550A1/xx active
- 1998-07-01 BR BR9810544-2A patent/BR9810544A/pt not_active IP Right Cessation
- 1998-07-01 HU HU0002330A patent/HUP0002330A3/hu unknown
- 1998-07-01 PE PE1998000589A patent/PE83999A1/es not_active Application Discontinuation
- 1998-07-01 ID IDW20000006A patent/ID24090A/id unknown
- 1998-07-01 US US09/423,771 patent/US6262046B1/en not_active Expired - Fee Related
- 1998-07-01 CN CN98806898A patent/CN1261887A/zh active Pending
- 1998-07-01 KR KR1020007000013A patent/KR20010015532A/ko not_active Abandoned
- 1998-07-01 EA EA199901102A patent/EA002773B1/ru not_active IP Right Cessation
- 1998-07-01 UY UY25079A patent/UY25079A1/es not_active IP Right Cessation
- 1998-07-01 TR TR2000/00025T patent/TR200000025T2/xx unknown
- 1998-07-01 HR HR970497A patent/HRP20000002B1/xx not_active IP Right Cessation
- 1998-07-01 EP EP98939619A patent/EP1023285A1/en not_active Withdrawn
- 1998-07-01 SK SK1827-99A patent/SK182799A3/sk unknown
- 1998-07-01 PL PL98338004A patent/PL338004A1/xx unknown
- 1998-07-01 IL IL13343398A patent/IL133433A0/xx unknown
- 1998-07-01 AU AU88062/98A patent/AU726708B2/en not_active Ceased
- 1998-07-02 AR ARP980103228A patent/AR013171A1/es not_active Application Discontinuation
- 1998-07-02 AP APAP/P/1998/001291A patent/AP1110A/en active
- 1998-07-02 PA PA19988454601A patent/PA8454601A1/es unknown
- 1998-07-03 CO CO98037815A patent/CO4950604A1/es unknown
- 1998-07-03 ZA ZA9805875A patent/ZA985875B/xx unknown
- 1998-07-10 TN TNTNSN98127A patent/TNSN98127A1/fr unknown
- 1998-07-14 GT GT199800106A patent/GT199800106A/es unknown
1999
- 1999-12-10 IS IS5295A patent/IS5295A/is unknown
- 1999-12-10 NO NO996115A patent/NO996115L/no not_active Application Discontinuation
- 1999-12-13 BG BG103992A patent/BG103992A/xx unknown
- 1999-12-15 OA OA9900282A patent/OA11236A/en unknown

Also Published As

Publication number	Publication date
ZA985875B (en)	2000-01-10
JP2000511207A (ja)	2000-08-29
EP1023285A1 (en)	2000-08-02
GB9714129D0 (en)	1997-09-10
DZ2550A1 (fr)	2003-02-08
PE83999A1 (es)	1999-09-11
TW492960B (en)	2002-07-01
AR013171A1 (es)	2000-12-13
IS5295A (is)	1999-12-10
AP9801291A0 (en)	1998-09-30
BR9810544A (pt)	2000-09-05
AU726708B2 (en)	2000-11-16
HUP0002330A2 (hu)	2001-06-28
BG103992A (en)	2000-07-31
GT199800106A (es)	2000-01-05
HRP20000002B1 (en)	2002-06-30
US6262046B1 (en)	2001-07-17
KR20010015532A (ko)	2001-02-26
EA002773B1 (ru)	2002-08-29
MA26519A1 (fr)	2004-12-20
CN1261887A (zh)	2000-08-02
HUP0002330A3 (en)	2002-05-28
CO4950604A1 (es)	2000-09-01
ID24090A (id)	2000-07-06
HN1998003689A (es)	1999-01-08
CA2294193A1 (en)	1999-01-14
SK182799A3 (en)	2001-11-06
TNSN98127A1 (fr)	2005-03-15
EA199901102A1 (ru)	2000-08-28
PA8454601A1 (es)	2000-05-24
UY25079A1 (es)	2000-12-29
IL133433A0 (en)	2001-04-30
WO1999001451A1 (en)	1999-01-14
NZ501715A (en)	2001-06-29
NO996115D0 (no)	1999-12-10
NO996115L (no)	2000-02-22
HRP20000002A2 (en)	2000-12-31
AP1110A (en)	2002-10-10
AU8806298A (en)	1999-01-25
PL338004A1 (en)	2000-09-25
TR200000025T2 (tr)	2000-06-21

Publication	Publication Date	Title
US6262046B1 (en)	2001-07-17	Azetidinylpropylpiperidine derivatives, intermediates and use as tachykinin antagonists
EP0862567B1 (en)	2001-08-01	5-azabicyclo(3.1.0)hexylalkyl-2-piperidones and -glutarimides as neurokinin receptor antagonists
NO311977B1 (no)	2002-02-25	(Azetidin-1-ylalkyl) laktamer som tachykinin-antagonister
EP0861251A1 (en)	1998-09-02	Morpholine derivatives and their use as therapeutic agents
JPH11501640A (ja)	1999-02-09	５−ｈｔ▲下４▼拮抗作用を有するジ−置換１，４−ピペリジンエステル類及びアミド類
US6242438B1 (en)	2001-06-05	3-Azetidinylalkylpiperidines or -pyrrolidines as tachykinin antagonists
US5846965A (en)	1998-12-08	3-aza and 3-oxa piperidone tachykinin antagonists
US6022971A (en)	2000-02-08	Azetidines
HRP20030923A2 (en)	2004-02-29	Novel piperidinecarboxamide derivatives, method for prreparing same and pharmaceutical compositions containing same
EP1150970A1 (fr)	2001-11-07	Derives de (1-phenacy-3-phenyl-3-piperidylethyl)piperidine, procede pour leur obtention et compositions pharmaceutiques les contenant
MXPA99012092A (es)	2000-08-01	Azetidinas
CZ9904659A3 (cs)	2000-10-11	Azetidinylpropylpiperidinové deriváty, meziprodukty a jejich použití jako tachykininových antagonistů
HK1029585A (en)	2001-04-06	Azetidinylpropylpiperidine derivatives, intermediates and use as tachykinin antagonists