OA10518A - Pyrrolidinyl hydroxamic acid compounds and their production process - Google Patents

Pyrrolidinyl hydroxamic acid compounds and their production process Download PDF

Info

Publication number: OA10518A
Authority: OA; OAPI
Prior art keywords: hydroxy; formula; phenyl; compound; hydrogen
Prior art date: 1995-03-31

Application number

OA70091A

Other languages

English (en)

Inventor

Fumitaka Ito

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.)

1995-03-31

Filing date

1997-09-30

Publication date

2002-04-22

1997-09-30 Application filed by Pfizer filed Critical Pfizer

2002-04-22 Publication of OA10518A publication Critical patent/OA10518A/en

Links

150000001875 compounds Chemical class 0.000 title claims abstract description 64
-1 Pyrrolidinyl hydroxamic Chemical compound 0.000 title claims abstract description 26
238000004519 manufacturing process Methods 0.000 title claims description 4
239000002253 acid Substances 0.000 title description 11
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 81
239000001257 hydrogen Substances 0.000 claims abstract description 77
238000000034 method Methods 0.000 claims abstract description 47
125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 39
125000006239 protecting group Chemical group 0.000 claims abstract description 22
125000003545 alkoxy group Chemical group 0.000 claims abstract description 16
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 13
125000001424 substituent group Chemical group 0.000 claims abstract description 9
125000004435 hydrogen atom Chemical class [H]* 0.000 claims abstract description 7
ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical group C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims abstract description 6
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims abstract description 5
125000005530 alkylenedioxy group Chemical group 0.000 claims abstract description 3
125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims abstract description 3
125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 claims abstract description 3
239000004305 biphenyl Chemical group 0.000 claims abstract description 3
235000010290 biphenyl Nutrition 0.000 claims abstract description 3
125000002541 furyl group Chemical group 0.000 claims abstract description 3
125000003392 indanyl group Chemical group C1(CCC2=CC=CC=C12)* 0.000 claims abstract description 3
125000001624 naphthyl group Chemical group 0.000 claims abstract description 3
125000004076 pyridyl group Chemical group 0.000 claims abstract description 3
125000001544 thienyl group Chemical group 0.000 claims abstract description 3
JCXJVPUVTGWSNB-UHFFFAOYSA-N Nitrogen dioxide Chemical compound O=[N]=O JCXJVPUVTGWSNB-UHFFFAOYSA-N 0.000 claims abstract 2
239000000203 mixture Substances 0.000 claims description 35
DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims description 22
150000002431 hydrogen Chemical class 0.000 claims description 19
125000000217 alkyl group Chemical group 0.000 claims description 14
238000006243 chemical reaction Methods 0.000 claims description 12
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 11
FPQQSJJWHUJYPU-UHFFFAOYSA-N 3-(dimethylamino)propyliminomethylidene-ethylazanium;chloride Chemical compound Cl.CCN=C=NCCCN(C)C FPQQSJJWHUJYPU-UHFFFAOYSA-N 0.000 claims description 7
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 6
QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 claims description 6
AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 claims description 5
239000012359 Methanesulfonyl chloride Substances 0.000 claims description 5
230000029936 alkylation Effects 0.000 claims description 4
238000005804 alkylation reaction Methods 0.000 claims description 4
LMDZBCPBFSXMTL-UHFFFAOYSA-N 1-Ethyl-3-(3-dimethylaminopropyl)carbodiimide Substances CCN=C=NCCCN(C)C LMDZBCPBFSXMTL-UHFFFAOYSA-N 0.000 claims description 3
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 3
125000001412 tetrahydropyranyl group Chemical group 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
125000005843 halogen group Chemical group 0.000 claims 3
150000001732 carboxylic acid derivatives Chemical class 0.000 claims 2
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125000001309 chloro group Chemical group Cl* 0.000 claims 1
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125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 claims 1
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 1
125000002221 trityl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C([*])(C1=C(C(=C(C(=C1[H])[H])[H])[H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims 1
150000003839 salts Chemical class 0.000 abstract description 17
239000003795 chemical substances by application Substances 0.000 abstract description 8
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125000000229 (C1-C4)alkoxy group Chemical group 0.000 abstract description 3
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VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 52
101150041968 CDC13 gene Proteins 0.000 description 49
HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 49
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YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 24
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XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 12
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 10
238000004440 column chromatography Methods 0.000 description 10
230000000694 effects Effects 0.000 description 10
125000006237 oxymethylenoxy group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 10
238000003756 stirring Methods 0.000 description 10
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 8
238000001914 filtration Methods 0.000 description 8
XLYOFNOQVPJJNP-ZSJDYOACSA-N heavy water Substances [2H]O[2H] XLYOFNOQVPJJNP-ZSJDYOACSA-N 0.000 description 7
239000002632 kappa opiate receptor agonist Substances 0.000 description 7
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YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 description 6
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-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
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
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WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
ZOUPGSMSNQLUNW-UHFFFAOYSA-N 2-(3,4-dichlorophenyl)acetic acid Chemical compound OC(=O)CC1=CC=C(Cl)C(Cl)=C1 ZOUPGSMSNQLUNW-UHFFFAOYSA-N 0.000 description 5
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 5
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 5
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239000000047 product Substances 0.000 description 5
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 4
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 4
WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 4
241000282412 Homo Species 0.000 description 4
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 4
208000006011 Stroke Diseases 0.000 description 4
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BQJCRHHNABKAKU-KBQPJGBKSA-N morphine Chemical compound O([C@H]1[C@H](C=C[C@H]23)O)C4=C5[C@@]12CCN(C)[C@@H]3CC5=CC=C4O BQJCRHHNABKAKU-KBQPJGBKSA-N 0.000 description 4
238000000746 purification Methods 0.000 description 4
238000010561 standard procedure Methods 0.000 description 4
238000012360 testing method Methods 0.000 description 4
GVNVAWHJIKLAGL-UHFFFAOYSA-N 2-(cyclohexen-1-yl)cyclohexan-1-one Chemical compound O=C1CCCCC1C1=CCCCC1 GVNVAWHJIKLAGL-UHFFFAOYSA-N 0.000 description 3
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
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Classifications

- C—CHEMISTRY; METALLURGY
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- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
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- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
- C07D295/12—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly or doubly bound nitrogen atoms
- C07D295/125—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly or doubly bound nitrogen atoms with the ring nitrogen atoms and the substituent nitrogen atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings
- C07D295/13—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly or doubly bound nitrogen atoms with the ring nitrogen atoms and the substituent nitrogen atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings to an acyclic saturated chain
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- C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D307/78—Benzo [b] furans; Hydrogenated benzo [b] furans
- C07D307/79—Benzo [b] furans; Hydrogenated benzo [b] furans with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the hetero ring
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- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links
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- C07D409/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
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OA70091A 1995-03-31 1997-09-30 Pyrrolidinyl hydroxamic acid compounds and their production process OA10518A (en)

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JP9500631		1995-03-31

Publications (1)

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OA10518A true OA10518A (en)	2002-04-22

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OA70091A OA10518A (en)	1995-03-31	1997-09-30	Pyrrolidinyl hydroxamic acid compounds and their production process

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US (2)	US5952369A (is)
EP (1)	EP0817772B1 (is)
JP (1)	JP3035356B2 (is)
KR (1)	KR100258657B1 (is)
AP (1)	AP625A (is)
AR (1)	AR002729A1 (is)
AT (1)	ATE231840T1 (is)
AU (1)	AU693336B2 (is)
BG (1)	BG62611B1 (is)
BR (1)	BR9607750A (is)
CA (1)	CA2213815C (is)
CZ (1)	CZ306497A3 (is)
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DK (1)	DK0817772T3 (is)
ES (1)	ES2188743T3 (is)
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HU (1)	HUP9900767A3 (is)
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MA (1)	MA23832A1 (is)
NO (1)	NO974513D0 (is)
NZ (1)	NZ304113A (is)
OA (1)	OA10518A (is)
PE (1)	PE43397A1 (is)
PL (1)	PL322652A1 (is)
RU (1)	RU2144917C1 (is)
SI (1)	SI9620039A (is)
SK (1)	SK129897A3 (is)
TN (1)	TNSN96045A1 (is)
TR (1)	TR199701082T1 (is)
TW (1)	TW408111B (is)
WO (1)	WO1996030339A1 (is)
YU (1)	YU18696A (is)
ZA (1)	ZA962476B (is)

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TNSN97092A1 (ar)	1996-09-18	1999-12-31	Agouron Pharma	مثبطات انزيم بروتيني فلزي وتركيبات صيدلانية تحتوي على تلك المثبتطات واستخدامها الصيدلاني وطرق ومركبات وسيطة مفيدة لتحضير التركيبات المذكورة.
JP4167302B2 (ja) *	1996-12-02	2008-10-15	杏林製薬株式会社	新規ｎ―置換ピロリジン誘導体及びその製造法
EP0973737A4 (en) *	1997-01-10	2000-04-26	Merck & Co Inc	EFFICIENT SYNTHESIS OF A CHIRAL MEDIATOR
IL130429A0 (en) *	1998-08-24	2000-06-01	Pfizer Prod Inc	Process for preparing pyrrolidinyl hydroxamic acid compounds
KR100295740B1 (ko) *	1998-09-17	2001-11-05	박영구	N-치환된-하이드록시고리화알킬아민유도체의제조방법
US6444829B1 (en) *	2000-07-19	2002-09-03	Hoffmann-La Roche Inc.	Pyrrolidine compounds
CA2445874A1 (en)	2001-04-30	2002-11-07	Fumitaka Ito	Process for preparing hydroxypyrrolidinyl ethylamine compounds useful as kappa agonists
US7091357B2 (en) *	2001-12-26	2006-08-15	University Of Kentucky Research Foundation	Chain-modified pyridino-N substituted nicotine compounds for use in the treatment of CNS pathologies
GB0202873D0 (en) *	2002-02-07	2002-03-27	Novartis Ag	Organic compounds
AU2003269399A1 (en) *	2002-11-01	2004-05-25	Pfizer Products Inc.	Process for the preparation of pyrrolidinyl ethylamine compounds via a copper-mediated aryl amination
RS20050760A (sr) *	2003-04-14	2008-04-04	Warner-Lambert Company Llc.,	Postupak za izradu fenilamida 5-(4- fluorofenil)-1-(2-((2r, 4r)-4-hidroksi- 6-okso-tetrahidro-piran-2-il)etil)-2- izopropil-4-fenil-1h-pirol-3- karboksilne kiseline
UA89035C2 (ru) *	2003-12-03	2009-12-25	Лео Фарма А/С	Эфиры гидроксамовых кислот и их фармацевтическое применение
GB0821010D0 (en)	2008-11-17	2008-12-24	Univ Warwick	Plant development control composition
US9493451B2 (en)	2011-05-16	2016-11-15	Bionomics Limited	Amine derivatives as potassium channel blockers
AU2013230425B2 (en)	2012-03-05	2017-05-25	Dr.Reddy's Laboratories Ltd.	Substituted heterocyclic acetamides as kappa opioid receptor (kor) agonists
GB201210395D0 (en) *	2012-06-11	2012-07-25	Syngenta Participations Ag	Crop enhancement compositions

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US3268539A (en) *	1963-05-20	1966-08-23	Universal Oil Prod Co	Tertiary-aminoalkyl derivatives of diaryl substituted acetohydroxamic acid esters

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1997
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1999
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Also Published As

Publication number	Publication date
KR100258657B1 (ko)	2000-07-01
HUP9900767A3 (en)	2001-01-29
PE43397A1 (es)	1997-10-13
DE69626009T2 (de)	2003-08-14
WO1996030339A1 (en)	1996-10-03
DE69626009D1 (de)	2003-03-06
MX9707454A (es)	1998-07-31
KR19980703476A (ko)	1998-11-05
BG62611B1 (bg)	2000-03-31
CA2213815C (en)	2001-12-18
AU5121196A (en)	1996-10-16
BG101896A (en)	1999-01-29
TNSN96045A1 (fr)	2005-03-15
US5952369A (en)	1999-09-14
US6110947A (en)	2000-08-29
HUP9900767A2 (hu)	1999-07-28
JPH11501048A (ja)	1999-01-26
CZ306497A3 (cs)	1998-07-15
TW408111B (en)	2000-10-11
AP9600791A0 (en)	1996-04-30
LV11971A (lv)	1998-02-20
BR9607750A (pt)	1998-06-30
TR199701082T1 (xx)	1998-02-21
LV11971B (en)	1998-06-20
ZA962476B (en)	1997-09-29
MA23832A1 (fr)	1996-10-01
YU18696A (sh)	1999-06-15
ES2188743T3 (es)	2003-07-01
JP3035356B2 (ja)	2000-04-24
PL322652A1 (en)	1998-02-16
SK129897A3 (en)	1998-11-04
SI9620039A (sl)	1998-08-31
HRP960141A2 (en)	1997-10-31
NO974513L (no)	1997-09-29
AU693336B2 (en)	1998-06-25
EP0817772B1 (en)	2003-01-29
AP625A (en)	1997-12-24
IS4547A (is)	1997-08-19
RU2144917C1 (ru)	2000-01-27
CA2213815A1 (en)	1996-10-03
IL129479A0 (en)	2000-02-29
DK0817772T3 (da)	2003-05-19
IL117440A0 (en)	1996-07-23
NO974513D0 (no)	1997-09-29
NZ304113A (en)	1999-01-28
ATE231840T1 (de)	2003-02-15
AR002729A1 (es)	1998-04-29
EP0817772A1 (en)	1998-01-14

Publication	Publication Date	Title
OA10518A (en)	2002-04-22	Pyrrolidinyl hydroxamic acid compounds and their production process
JP2818958B2 (ja)	1998-10-30	４―（４―アルコキシフェニル）―２―ブチルアミン誘導体およびその製造法
KR100523184B1 (ko)	2005-10-24	아제티딘 및 피롤리딘의 유도체
CN103080088B (zh)	2014-09-24	用于合成药物的中间体化合物的制备方法
KR20040093123A (ko)	2004-11-04	Ｎｋ1 길항제
JP2935899B2 (ja)	1999-08-16	▲下ｋ▼レセプターアゴニストとしてのｎ−（２−（ピロリジニル−１）−１−フェニルエチル）アセトアミド
Liu et al.	2017	Divergent syntheses of L-733, 060 and CP-122721 from functionalized pieridinones made by one-pot tandem cyclization
JP3478827B2 (ja)	2003-12-15	アミド誘導体
KR20010042750A (ko)	2001-05-25	거울상 이성질체-유리ｎ-메틸-ｎ-[(1ｓ)-1-페닐-2-((3ｓ)-3-히드록시피롤리딘-1-일)에틸]-2,2-디페닐아세트아미드의 제조 방법
US5554581A (en)	1996-09-10	Tetrahydrophthalamide derivative, intermediate for producing the same, production of both, and herbicide containing the same as active ingredient
US6150417A (en)	2000-11-21	Phenoxyethylamine derivatives, method of preparation application as medicine and pharmaceutical compositions containing same
JP2003535845A (ja)	2003-12-02	プロパノールアミノテトラリン類、その製造及びそれらを含む組成物
MXPA97007454A (en)	1998-11-09	Hydroxamic pirrolidinil acid compounds and their product procedure
JPH03176496A (ja)	1991-07-31	フェロセニル誘導体及びその利用
Leathen	2011	The Development of Reactions for the Stereoselective Synthesis of Heterocycles and Benzylic Amines, and Exploration of Bisisoxazolidines as Small Molecule Transcriptional Activation Domains
JP2012107006A (ja)	2012-06-07	Ｎ−置換−環状アミノ誘導体の製造方法
HK1184787B (en)	2015-08-21	Production method of intermediate compound for synthesizing medicament
EP2396334A1 (fr)	2011-12-21	Derives de n-[(2-aza-bicyclo[2.1.1]hex-1-yl]-aryl-methyl]-benzamide, leur preparation et leur application en therapeutique
CS205086B2 (cs)	1981-04-30	Způsob výroby hydroxyderivátů aryloxy- a arylthioperhydroazaheterocyklů
HK1200818B (en)	2018-01-19	(3,4-dichloro-phenyl)-((s)-3-propyl-pyrrolidin-3-yl)-methanone hydrochloride and manufacturing processes
JP2002241353A (ja)	2002-08-28	光学活性アミン誘導体および合成法