BG100218A - Енантиомери на 4-(5-флуоро-2,3-дихидро-1н-инден-2-ил)- 1н-имидазол - Google Patents

Енантиомери на 4-(5-флуоро-2,3-дихидро-1н-инден-2-ил)- 1н-имидазол Download PDF

Info

Publication number: BG100218A
Authority: BG; Bulgaria
Prior art keywords: imidazole; inden; dihydro; fluoro; enantiomer
Prior art date: 1993-06-18

Application number

BG100218A

Other languages

Bulgarian (bg)

English (en)

Inventor

Arto Karjalainen

Raimo Virtanen

Arja Karjalainen

Seppo Parhi

Maire Eloranta

Antti Haapalinna

Original Assignee

Orion- Yhtymae Oy

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.)

1993-06-18

Filing date

1995-12-13

Publication date

1996-06-28

1995-12-13 Application filed by Orion- Yhtymae Oy filed Critical Orion- Yhtymae Oy

1996-06-28 Publication of BG100218A publication Critical patent/BG100218A/bg

Links

SRTZGTVJBSGUPX-UHFFFAOYSA-N 5-(5-fluoro-2,3-dihydro-1h-inden-2-yl)-1h-imidazole Chemical compound C1C2=CC(F)=CC=C2CC1C1=CNC=N1 SRTZGTVJBSGUPX-UHFFFAOYSA-N 0.000 title claims abstract description 17
HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 title description 7
150000003839 salts Chemical class 0.000 claims abstract description 11
238000002360 preparation method Methods 0.000 claims abstract description 5
239000002253 acid Substances 0.000 claims description 9
FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 claims description 8
-1 5-fluoro-2,3-dihydro-1H-inden-2-yl Chemical group 0.000 claims description 6
238000006243 chemical reaction Methods 0.000 claims description 6
238000000034 method Methods 0.000 claims description 5
238000001640 fractional crystallisation Methods 0.000 claims description 3
239000011833 salt mixture Substances 0.000 claims 4
239000012458 free base Substances 0.000 claims 2
XNSBRSZLJZUOJH-UHFFFAOYSA-N 5-fluoro-2,3-dihydro-1h-indene Chemical compound FC1=CC=C2CCCC2=C1 XNSBRSZLJZUOJH-UHFFFAOYSA-N 0.000 claims 1
230000003287 optical effect Effects 0.000 abstract description 5
208000028698 Cognitive impairment Diseases 0.000 abstract description 4
208000010877 cognitive disease Diseases 0.000 abstract description 4
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 30
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 13
241000700159 Rattus Species 0.000 description 12
230000000694 effects Effects 0.000 description 11
239000000243 solution Substances 0.000 description 11
230000015654 memory Effects 0.000 description 7
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Substances C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 6
238000012549 training Methods 0.000 description 6
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
239000005557 antagonist Substances 0.000 description 5
150000001875 compounds Chemical class 0.000 description 5
239000003814 drug Substances 0.000 description 5
239000000203 mixture Substances 0.000 description 5
238000012360 testing method Methods 0.000 description 5
239000000556 agonist Substances 0.000 description 4
HSWPZIDYAHLZDD-UHFFFAOYSA-N atipamezole Chemical compound C1C2=CC=CC=C2CC1(CC)C1=CN=CN1 HSWPZIDYAHLZDD-UHFFFAOYSA-N 0.000 description 4
229960003002 atipamezole Drugs 0.000 description 4
229940079593 drug Drugs 0.000 description 4
238000002474 experimental method Methods 0.000 description 4
238000004128 high performance liquid chromatography Methods 0.000 description 4
239000000047 product Substances 0.000 description 4
LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 4
XXSQJWQCFIRWNW-UHFFFAOYSA-N 2-(1h-imidazol-5-yl)-2,3-dihydro-1h-inden-5-amine Chemical compound C1C2=CC(N)=CC=C2CC1C1=CNC=N1 XXSQJWQCFIRWNW-UHFFFAOYSA-N 0.000 description 3
241001465754 Metazoa Species 0.000 description 3
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 3
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
239000007864 aqueous solution Substances 0.000 description 3
239000012153 distilled water Substances 0.000 description 3
KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 3
RILZRCJGXSFXNE-UHFFFAOYSA-N 2-[4-(trifluoromethoxy)phenyl]ethanol Chemical compound OCCC1=CC=C(OC(F)(F)F)C=C1 RILZRCJGXSFXNE-UHFFFAOYSA-N 0.000 description 2
PRPKJGGEZMASQX-UHFFFAOYSA-N 5-(2,3-dihydro-1h-inden-2-yl)-1h-imidazole;hydrochloride Chemical compound Cl.C1C2=CC=CC=C2CC1C1=CNC=N1 PRPKJGGEZMASQX-UHFFFAOYSA-N 0.000 description 2
108060003345 Adrenergic Receptor Proteins 0.000 description 2
102000017910 Adrenergic receptor Human genes 0.000 description 2
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
238000004458 analytical method Methods 0.000 description 2
WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 description 2
239000003054 catalyst Substances 0.000 description 2
JXMXDKHEZLKQPB-UHFFFAOYSA-N detomidine Chemical compound CC1=CC=CC(CC=2[N]C=NC=2)=C1C JXMXDKHEZLKQPB-UHFFFAOYSA-N 0.000 description 2
229960001894 detomidine Drugs 0.000 description 2
239000012954 diazonium Substances 0.000 description 2
IJGRMHOSHXDMSA-UHFFFAOYSA-O diazynium Chemical compound [NH+]#N IJGRMHOSHXDMSA-UHFFFAOYSA-O 0.000 description 2
WGLUMOCWFMKWIL-UHFFFAOYSA-N dichloromethane;methanol Chemical compound OC.ClCCl WGLUMOCWFMKWIL-UHFFFAOYSA-N 0.000 description 2
239000000284 extract Substances 0.000 description 2
239000000706 filtrate Substances 0.000 description 2
238000003818 flash chromatography Methods 0.000 description 2
229910052739 hydrogen Inorganic materials 0.000 description 2
AUONNNVJUCSETH-UHFFFAOYSA-N icosanoyl icosanoate Chemical compound CCCCCCCCCCCCCCCCCCCC(=O)OC(=O)CCCCCCCCCCCCCCCCCCC AUONNNVJUCSETH-UHFFFAOYSA-N 0.000 description 2
229940079865 intestinal antiinfectives imidazole derivative Drugs 0.000 description 2
230000004118 muscle contraction Effects 0.000 description 2
CMUOJBJRZUHRMU-UHFFFAOYSA-N nitrourea Chemical compound NC(=O)N[N+]([O-])=O CMUOJBJRZUHRMU-UHFFFAOYSA-N 0.000 description 2
SONNWYBIRXJNDC-VIFPVBQESA-N phenylephrine Chemical compound CNC[C@H](O)C1=CC=CC(O)=C1 SONNWYBIRXJNDC-VIFPVBQESA-N 0.000 description 2
229960001802 phenylephrine Drugs 0.000 description 2
239000002244 precipitate Substances 0.000 description 2
238000001953 recrystallisation Methods 0.000 description 2
238000000926 separation method Methods 0.000 description 2
235000010288 sodium nitrite Nutrition 0.000 description 2
239000007787 solid Substances 0.000 description 2
230000001225 therapeutic effect Effects 0.000 description 2
210000001177 vas deferen Anatomy 0.000 description 2
OXYOLJGIYXSJHS-UHFFFAOYSA-N 5-(5-fluoro-2,3-dihydro-1h-inden-2-yl)-1h-imidazole;hydrochloride Chemical compound Cl.C1C2=CC(F)=CC=C2CC1C1=CNC=N1 OXYOLJGIYXSJHS-UHFFFAOYSA-N 0.000 description 1
DLURUQQMVLOLCP-UHFFFAOYSA-N 5-nitro-2,3-dihydro-1h-indene Chemical compound [O-][N+](=O)C1=CC=C2CCCC2=C1 DLURUQQMVLOLCP-UHFFFAOYSA-N 0.000 description 1
229910015900 BF3 Inorganic materials 0.000 description 1
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
150000000994 L-ascorbates Chemical class 0.000 description 1
241000699670 Mus sp. Species 0.000 description 1
229910019142 PO4 Inorganic materials 0.000 description 1
230000007059 acute toxicity Effects 0.000 description 1
231100000403 acute toxicity Toxicity 0.000 description 1
102000015007 alpha-adrenergic receptor activity proteins Human genes 0.000 description 1
108040006816 alpha-adrenergic receptor activity proteins Proteins 0.000 description 1
238000000540 analysis of variance Methods 0.000 description 1
230000008485 antagonism Effects 0.000 description 1
239000008346 aqueous phase Substances 0.000 description 1
235000010323 ascorbic acid Nutrition 0.000 description 1
239000012298 atmosphere Substances 0.000 description 1
150000001558 benzoic acid derivatives Chemical class 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
230000037396 body weight Effects 0.000 description 1
150000003842 bromide salts Chemical class 0.000 description 1
229910052799 carbon Inorganic materials 0.000 description 1
125000004432 carbon atom Chemical group C* 0.000 description 1
238000009903 catalytic hydrogenation reaction Methods 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
150000001805 chlorine compounds Chemical class 0.000 description 1
150000001860 citric acid derivatives Chemical class 0.000 description 1
230000003930 cognitive ability Effects 0.000 description 1
239000012141 concentrate Substances 0.000 description 1
230000008602 contraction Effects 0.000 description 1
239000012043 crude product Substances 0.000 description 1
230000007423 decrease Effects 0.000 description 1
239000003937 drug carrier Substances 0.000 description 1
239000003480 eluent Substances 0.000 description 1
230000002708 enhancing effect Effects 0.000 description 1
201000010063 epididymitis Diseases 0.000 description 1
MVEAAGBEUOMFRX-UHFFFAOYSA-N ethyl acetate;hydrochloride Chemical compound Cl.CCOC(C)=O MVEAAGBEUOMFRX-UHFFFAOYSA-N 0.000 description 1
150000004675 formic acid derivatives Chemical class 0.000 description 1
238000009472 formulation Methods 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
239000001257 hydrogen Substances 0.000 description 1
238000000338 in vitro Methods 0.000 description 1
125000003392 indanyl group Chemical group C1(CCC2=CC=CC=C12)* 0.000 description 1
239000004615 ingredient Substances 0.000 description 1
239000007924 injection Substances 0.000 description 1
238000002347 injection Methods 0.000 description 1
230000003993 interaction Effects 0.000 description 1
239000007788 liquid Substances 0.000 description 1
150000002688 maleic acid derivatives Chemical class 0.000 description 1
238000005259 measurement Methods 0.000 description 1
206010027175 memory impairment Diseases 0.000 description 1
150000007522 mineralic acids Chemical class 0.000 description 1
150000002823 nitrates Chemical class 0.000 description 1
230000000802 nitrating effect Effects 0.000 description 1
238000006396 nitration reaction Methods 0.000 description 1
150000002828 nitro derivatives Chemical class 0.000 description 1
150000007524 organic acids Chemical class 0.000 description 1
239000012074 organic phase Substances 0.000 description 1
239000003960 organic solvent Substances 0.000 description 1
239000004031 partial agonist Substances 0.000 description 1
230000000144 pharmacologic effect Effects 0.000 description 1
239000012071 phase Substances 0.000 description 1
235000021317 phosphate Nutrition 0.000 description 1
150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
239000011148 porous material Substances 0.000 description 1
210000002307 prostate Anatomy 0.000 description 1
239000011541 reaction mixture Substances 0.000 description 1
102000005962 receptors Human genes 0.000 description 1
108020003175 receptors Proteins 0.000 description 1
239000013558 reference substance Substances 0.000 description 1
238000011160 research Methods 0.000 description 1
150000003873 salicylate salts Chemical class 0.000 description 1
238000007619 statistical method Methods 0.000 description 1
150000003871 sulfonates Chemical class 0.000 description 1
150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
150000003892 tartrate salts Chemical class 0.000 description 1
238000005979 thermal decomposition reaction Methods 0.000 description 1
230000003936 working memory Effects 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D233/64—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms, e.g. histidine

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

BG100218A 1993-06-18 1995-12-13 Енантиомери на 4-(5-флуоро-2,3-дихидро-1н-инден-2-ил)- 1н-имидазол BG100218A (bg)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
GB939312669A GB9312669D0 (en)	1993-06-18	1993-06-18	New opticla isomers
PCT/FI1994/000263 WO1995000492A1 (en)	1993-06-18	1994-06-16	Enantiomers of 4-(5-fluoro-2,3-dihydro-1h-inden-2-yl)-1h-imidazole

Publications (1)

Publication Number	Publication Date
BG100218A true BG100218A (bg)	1996-06-28

Family

ID=10737432

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
BG100218A BG100218A (bg)	1993-06-18	1995-12-13	Енантиомери на 4-(5-флуоро-2,3-дихидро-1н-инден-2-ил)- 1н-имидазол

Country Status (19)

Country	Link
EP (1)	EP0703903A1 (lt)
JP (1)	JPH08511554A (lt)
CN (1)	CN1125439A (lt)
AU (1)	AU6972594A (lt)
BG (1)	BG100218A (lt)
CA (1)	CA2165459A1 (lt)
CZ (1)	CZ332195A3 (lt)
EE (1)	EE9400010A (lt)
GB (1)	GB9312669D0 (lt)
HU (1)	HU211271A9 (lt)
IL (1)	IL109984A0 (lt)
LT (1)	LT3468B (lt)
LV (1)	LV11462B (lt)
NO (1)	NO955056L (lt)
NZ (1)	NZ267427A (lt)
PL (1)	PL312194A1 (lt)
SK (1)	SK157095A3 (lt)
WO (1)	WO1995000492A1 (lt)
ZA (1)	ZA944346B (lt)

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US6613907B2 (en)	2000-11-08	2003-09-02	Amr Technology, Inc.	Process for the production of piperidine derivatives with microorganisms
US8188126B2 (en)	2002-05-16	2012-05-29	Pierre Fabre Medicament	Imidazolic compounds and use thereof as alpha-2 adrenergic receptors
FR2839719B1 (fr) *	2002-05-16	2004-08-06	Pf Medicament	Nouveaux composes imidazoliques, leur procede de preparation et leur utilisation a titre de medicaments
GB0226076D0 (en) *	2002-11-08	2002-12-18	Rp Scherer Technologies Inc	Improved formulations containing substituted imidazole derivatives

Family Cites Families (5)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
GB2167408B (en)	1984-11-23	1988-05-25	Farmos Oy	Substituted imidazole derivatives and their preparation and use
FI81092C (fi)	1986-05-15	1990-09-10	Farmos Oy	Foerfarande foer framstaellning av terapeutiskt aktiva 4(5)-(2,3-dihydro-1h-inden-2-yl)-imidazolderivat.
GB2225782A (en)	1988-12-09	1990-06-13	Farmos Group Limited	Imidazole derivatives useful for treatment of diabetes
GB2244431A (en)	1990-05-31	1991-12-04	Farmos Oy	Treatment of age related memory impairment and other cognitive disorders
GB9127050D0 (en) *	1991-12-20	1992-02-19	Orion Yhtymae Oy	Substituted imidazole derivatives and their preparation and use

1993
- 1993-06-18 GB GB939312669A patent/GB9312669D0/en active Pending
1994
- 1994-06-10 IL IL10998494A patent/IL109984A0/xx unknown
- 1994-06-15 EE EE9400010A patent/EE9400010A/xx unknown
- 1994-06-16 CZ CZ953321A patent/CZ332195A3/cs unknown
- 1994-06-16 EP EP94918395A patent/EP0703903A1/en not_active Withdrawn
- 1994-06-16 AU AU69725/94A patent/AU6972594A/en not_active Abandoned
- 1994-06-16 PL PL94312194A patent/PL312194A1/xx unknown
- 1994-06-16 SK SK1570-95A patent/SK157095A3/sk unknown
- 1994-06-16 CN CN94192476A patent/CN1125439A/zh active Pending
- 1994-06-16 WO PCT/FI1994/000263 patent/WO1995000492A1/en not_active Ceased
- 1994-06-16 NZ NZ267427A patent/NZ267427A/en unknown
- 1994-06-16 CA CA002165459A patent/CA2165459A1/en not_active Abandoned
- 1994-06-16 JP JP7502468A patent/JPH08511554A/ja active Pending
- 1994-06-17 ZA ZA944346A patent/ZA944346B/xx unknown
- 1994-06-17 LT LTIP1959A patent/LT3468B/lt not_active IP Right Cessation
1995
- 1995-06-23 HU HU95P/P00421P patent/HU211271A9/hu unknown
- 1995-12-13 BG BG100218A patent/BG100218A/bg unknown
- 1995-12-13 NO NO955056A patent/NO955056L/no unknown
- 1995-12-19 LV LVP-95-376A patent/LV11462B/en unknown

Also Published As

Publication number	Publication date
LT3468B (en)	1995-10-25
SK157095A3 (en)	1996-06-05
HU211271A9 (en)	1995-11-28
EP0703903A1 (en)	1996-04-03
CA2165459A1 (en)	1995-01-05
AU6972594A (en)	1995-01-17
PL312194A1 (en)	1996-04-01
IL109984A0 (en)	1994-12-29
EE9400010A (et)	1995-12-15
LV11462B (en)	1996-12-20
LTIP1959A (en)	1995-01-31
JPH08511554A (ja)	1996-12-03
CZ332195A3 (en)	1996-05-15
NO955056D0 (no)	1995-12-13
NZ267427A (en)	1996-10-28
CN1125439A (zh)	1996-06-26
LV11462A (lv)	1996-08-20
WO1995000492A1 (en)	1995-01-05
GB9312669D0 (en)	1993-08-04
ZA944346B (en)	1995-02-15
NO955056L (no)	1995-12-13

Publication	Publication Date	Title
US5498623A (en)	1996-03-12	4(5) substituted imidazoles and their preparation and use
HK1008962B (en)	1999-05-21	Substituted imidazole derivatives and their preparation and use
SU1241986A3 (ru)	1986-06-30	Способ получени производных бензамида,их гидрохлоридов или оптических изомеров
FI67544C (fi)	1985-04-10	Foerfarande foer framstaellning av farmakologiskt vaerdefullt imidazolinderivat
EP0008249A2 (fr)	1980-02-20	Dérivés de fluorènes et fluoranthènes, leur procédé de préparation et leur application en thérapeutique
DE60100388T2 (de)	2004-05-19	Aminosäurederivate und deren verwendung als inhibitoren von nep, ace und ece
JP5095070B2 (ja)	2012-12-12	Ｒ−（−）−１−［２−（７−クロロベンゾ［ｂ］チオフェン−３−イル−メトキシ）−２−（２，４−ジクロロフェニル）−エチル］−１Ｈ−イミダゾール
JPS59141558A (ja)	1984-08-14	２−イミノ−ピロリジン類，その製造法および治療用組成物
BG100218A (bg)	1996-06-28	Енантиомери на 4-(5-флуоро-2,3-дихидро-1н-инден-2-ил)- 1н-имидазол
US5028616A (en)	1991-07-02	N-benzylpiperidine amides
US4567181A (en)	1986-01-28	Bicyclo (4.2.0) 1,3,5-octatriene compounds and use as α-adrenergics
JP4223237B2 (ja)	2009-02-12	３−フェニル−３，７−ジアザビシクロ［３，３，１］ノナン−化合物、これを含有する医薬品、その使用及びその製法
NO173010B (no)	1993-07-05	Analogifremgangsmaate for fremstilling av terapeutisk aktivt sulfonanilid
KR830001667B1 (ko)	1983-08-23	페닐 퀴놀리지딘의 제조방법
US4318909A (en)	1982-03-09	Benzoxazocines
US4626522A (en)	1986-12-02	Benzoxazocines intermediates
FI70212B (fi)	1986-02-28	Analogifoerfarande foer framstaellning av terapeutiskt aktiva 2-aminoalkyl-5-pyridinoler
US5137908A (en)	1992-08-11	4-azahexacyclododecane compounds
US4992446A (en)	1991-02-12	Tricyclic quinolizine amides
NO170630B (no)	1992-08-03	Analogifremgangsmaate ved fremstilling av nye, terapeutiskaktive 1-(3-(2-sek.-aminoetoksy)-2-tienyl)-3-fenyl-propanoner og syreaddisjonssalter derav
FR2462426A1 (fr)	1981-02-13	Nouveau derive de la 2-(1-naphtyl)piperidine, sa preparation et son application comme medicament
JPH0720934B2 (ja)	1995-03-08	新規１，４―ジヒドロピリジン誘導体
SI9300034A (sl)	1994-09-30	Substituirani derivati imidazola in njihova priprava in uporaea
FR2729148A1 (fr)	1996-07-12	Nouveaux derives d'amine, leur procede de preparation et leur utilisation en tant que medicaments et notamment en tant qu'agents anti-arythmiques
HU211151A9 (hu)	1995-10-30	Szubsztituált imidazolszármazékok, előállításuk és alkalmazásuk