JPH08511554A - 新規光学異性体 - Google Patents

新規光学異性体

Info

Publication number: JPH08511554A
Authority: JP; Japan
Prior art keywords: imidazole; dihydro; fluoro; inden; enantiomer
Prior art date: 1993-06-18
Legal status (The legal status 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 status listed.): Pending

Application number

JP7502468A

Other languages

English (en)

Japanese (ja)

Inventor

ヨハネスカルヤライネン、アルト

エイナリヴィルターネン、ライモ

レーナカルヤライネン、アルヤ

スレビレンナルトパルヒ、セッポ

マルヤタエロランタ、マイレ

サカリハアパリンナ、アンチ

Original Assignee

オリオン−ユヒチュメオサケユキチュア

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

1994-06-16

Publication date

1996-12-03

1994-06-16 Application filed by オリオン−ユヒチュメオサケユキチュア filed Critical オリオン−ユヒチュメオサケユキチュア

1996-12-03 Publication of JPH08511554A publication Critical patent/JPH08511554A/ja

Status Pending legal-status Critical Current

Links

230000003287 optical effect Effects 0.000 title abstract description 8
150000003839 salts Chemical class 0.000 claims abstract description 15
RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Substances C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims description 11
239000002253 acid Substances 0.000 claims description 10
239000000203 mixture Substances 0.000 claims description 9
-1 5-Fluoro-2,3-dihydro-1H-inden-2-yl Chemical group 0.000 claims description 7
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 7
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 claims description 6
FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 claims description 5
238000000034 method Methods 0.000 claims description 5
FEWJPZIEWOKRBE-LWMBPPNESA-N L-(+)-Tartaric acid Natural products OC(=O)[C@@H](O)[C@H](O)C(O)=O FEWJPZIEWOKRBE-LWMBPPNESA-N 0.000 claims description 4
239000012458 free base Substances 0.000 claims description 4
239000001358 L(+)-tartaric acid Substances 0.000 claims description 3
235000011002 L(+)-tartaric acid Nutrition 0.000 claims description 3
238000001640 fractional crystallisation Methods 0.000 claims description 3
AUONNNVJUCSETH-UHFFFAOYSA-N icosanoyl icosanoate Chemical compound CCCCCCCCCCCCCCCCCCCC(=O)OC(=O)CCCCCCCCCCCCCCCCCCC AUONNNVJUCSETH-UHFFFAOYSA-N 0.000 claims description 3
238000004519 manufacturing process Methods 0.000 claims description 2
XNSBRSZLJZUOJH-UHFFFAOYSA-N 5-fluoro-2,3-dihydro-1h-indene Chemical compound FC1=CC=C2CCCC2=C1 XNSBRSZLJZUOJH-UHFFFAOYSA-N 0.000 claims 3
SRTZGTVJBSGUPX-UHFFFAOYSA-N 5-(5-fluoro-2,3-dihydro-1h-inden-2-yl)-1h-imidazole Chemical class C1C2=CC(F)=CC=C2CC1C1=CNC=N1 SRTZGTVJBSGUPX-UHFFFAOYSA-N 0.000 abstract description 10
208000010877 cognitive disease Diseases 0.000 abstract description 5
238000002360 preparation method Methods 0.000 abstract description 3
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 30
241000700159 Rattus Species 0.000 description 13
230000000694 effects Effects 0.000 description 11
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
239000000243 solution Substances 0.000 description 10
150000001875 compounds Chemical class 0.000 description 9
238000012360 testing method Methods 0.000 description 9
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
239000003814 drug Substances 0.000 description 5
229940079593 drug Drugs 0.000 description 5
239000000556 agonist Substances 0.000 description 4
239000007864 aqueous solution Substances 0.000 description 4
239000002585 base Substances 0.000 description 4
238000004128 high performance liquid chromatography Methods 0.000 description 4
LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 4
QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 description 3
POPGTFGTDBMAIP-UHFFFAOYSA-N 5-(5-nitro-2,3-dihydro-1h-inden-2-yl)-1h-imidazole Chemical compound C1C2=CC([N+](=O)[O-])=CC=C2CC1C1=CNC=N1 POPGTFGTDBMAIP-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
239000000674 adrenergic antagonist Substances 0.000 description 3
239000005557 antagonist Substances 0.000 description 3
239000012153 distilled water Substances 0.000 description 3
229910052739 hydrogen Inorganic materials 0.000 description 3
229940079865 intestinal antiinfectives imidazole derivative Drugs 0.000 description 3
238000002844 melting Methods 0.000 description 3
230000008018 melting Effects 0.000 description 3
239000000047 product Substances 0.000 description 3
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 2
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
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
238000000540 analysis of variance Methods 0.000 description 2
HSWPZIDYAHLZDD-UHFFFAOYSA-N atipamezole Chemical compound C1C2=CC=CC=C2CC1(CC)C1=CN=CN1 HSWPZIDYAHLZDD-UHFFFAOYSA-N 0.000 description 2
229960003002 atipamezole Drugs 0.000 description 2
WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 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
239000003153 chemical reaction reagent Substances 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
239000000706 filtrate Substances 0.000 description 2
238000003818 flash chromatography Methods 0.000 description 2
PQNFLJBBNBOBRQ-UHFFFAOYSA-N indane Chemical compound C1=CC=C2CCCC2=C1 PQNFLJBBNBOBRQ-UHFFFAOYSA-N 0.000 description 2
QHDUJTCUPWHNPK-UHFFFAOYSA-N methyl 7-methoxy-2h-indazole-3-carboxylate Chemical compound COC1=CC=CC2=C(C(=O)OC)NN=C21 QHDUJTCUPWHNPK-UHFFFAOYSA-N 0.000 description 2
230000004118 muscle contraction Effects 0.000 description 2
239000008188 pellet Substances 0.000 description 2
239000002244 precipitate Substances 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
JDIIGWSSTNUWGK-UHFFFAOYSA-N 1h-imidazol-3-ium;chloride Chemical compound [Cl-].[NH2+]1C=CN=C1 JDIIGWSSTNUWGK-UHFFFAOYSA-N 0.000 description 1
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 1
229910015900 BF3 Inorganic materials 0.000 description 1
239000005711 Benzoic acid Substances 0.000 description 1
CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
KRKNYBCHXYNGOX-UHFFFAOYSA-K Citrate Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 description 1
BDAGIHXWWSANSR-UHFFFAOYSA-M Formate Chemical compound [O-]C=O BDAGIHXWWSANSR-UHFFFAOYSA-M 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
229910002651 NO3 Inorganic materials 0.000 description 1
NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 1
229910019142 PO4 Inorganic materials 0.000 description 1
QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
230000007059 acute toxicity Effects 0.000 description 1
231100000403 acute toxicity Toxicity 0.000 description 1
239000000670 adrenergic alpha-2 receptor antagonist Substances 0.000 description 1
230000008484 agonism Effects 0.000 description 1
102000004305 alpha Adrenergic Receptors Human genes 0.000 description 1
108090000861 alpha Adrenergic Receptors Proteins 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
230000009286 beneficial effect Effects 0.000 description 1
235000010233 benzoic acid Nutrition 0.000 description 1
230000037396 body weight Effects 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
238000006243 chemical reaction Methods 0.000 description 1
230000001143 conditioned effect Effects 0.000 description 1
230000008602 contraction Effects 0.000 description 1
239000012043 crude product Substances 0.000 description 1
238000002425 crystallisation Methods 0.000 description 1
230000008025 crystallization Effects 0.000 description 1
230000003247 decreasing effect Effects 0.000 description 1
JXMXDKHEZLKQPB-UHFFFAOYSA-N detomidine Chemical compound CC1=CC=CC(CC=2[N]C=NC=2)=C1C JXMXDKHEZLKQPB-UHFFFAOYSA-N 0.000 description 1
229960001894 detomidine Drugs 0.000 description 1
230000037213 diet Effects 0.000 description 1
235000005911 diet Nutrition 0.000 description 1
239000003937 drug carrier Substances 0.000 description 1
238000005485 electric heating Methods 0.000 description 1
239000003480 eluent Substances 0.000 description 1
230000002708 enhancing effect Effects 0.000 description 1
MVEAAGBEUOMFRX-UHFFFAOYSA-N ethyl acetate;hydrochloride Chemical compound Cl.CCOC(C)=O MVEAAGBEUOMFRX-UHFFFAOYSA-N 0.000 description 1
239000000284 extract Substances 0.000 description 1
238000009472 formulation Methods 0.000 description 1
239000003517 fume Substances 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
239000001257 hydrogen Substances 0.000 description 1
150000002460 imidazoles Chemical class 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
238000002347 injection Methods 0.000 description 1
239000007924 injection Substances 0.000 description 1
239000007788 liquid Substances 0.000 description 1
VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
206010027175 memory impairment Diseases 0.000 description 1
150000007522 mineralic acids Chemical class 0.000 description 1
238000012986 modification Methods 0.000 description 1
230000004048 modification Effects 0.000 description 1
230000000802 nitrating effect Effects 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
230000003285 pharmacodynamic effect Effects 0.000 description 1
230000000144 pharmacologic effect Effects 0.000 description 1
239000012071 phase Substances 0.000 description 1
SONNWYBIRXJNDC-VIFPVBQESA-N phenylephrine Chemical compound CNC[C@H](O)C1=CC=CC(O)=C1 SONNWYBIRXJNDC-VIFPVBQESA-N 0.000 description 1
229960001802 phenylephrine Drugs 0.000 description 1
NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
239000010452 phosphate Substances 0.000 description 1
230000003389 potentiating effect Effects 0.000 description 1
238000000197 pyrolysis Methods 0.000 description 1
239000011541 reaction mixture Substances 0.000 description 1
238000001953 recrystallisation Methods 0.000 description 1
239000013558 reference substance Substances 0.000 description 1
150000003873 salicylate salts Chemical class 0.000 description 1
238000000926 separation method Methods 0.000 description 1
238000007619 statistical method Methods 0.000 description 1
238000010254 subcutaneous injection Methods 0.000 description 1
239000007929 subcutaneous injection Substances 0.000 description 1
BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
235000002906 tartaric acid Nutrition 0.000 description 1
239000011975 tartaric acid Substances 0.000 description 1
229940095064 tartrate Drugs 0.000 description 1
210000001550 testis Anatomy 0.000 description 1
238000002560 therapeutic procedure Methods 0.000 description 1
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 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)

JP7502468A 1993-06-18 1994-06-16 新規光学異性体 Pending JPH08511554A (ja)

Applications Claiming Priority (3)

Application Number	Priority Date	Filing Date	Title
GB939312669A GB9312669D0 (en)	1993-06-18	1993-06-18	New opticla isomers
GB9312669.6		1993-06-18
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
JPH08511554A true JPH08511554A (ja)	1996-12-03

Family

ID=10737432

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
JP7502468A Pending JPH08511554A (ja)	1993-06-18	1994-06-16	新規光学異性体

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
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
BG100218A (bg)	1996-06-28
NO955056L (no)	1995-12-13

Publication	Publication Date	Title
US3262977A (en)	1966-07-26	N-aralkyl-1, 1-diphenyl-propylamine derivatives
JPS617245A (ja)	1986-01-13	アドレナリン性化合物
CS228917B2 (en)	1984-05-14	Method of preparing substituted derivatives of 1,4-dihydropyridine
HU185475B (en)	1985-02-28	Process for preparing /-/-n-methyl-3-/2-methyil-phenoxy/-3-phenyl-propyl-amine and salts thereof
US5498623A (en)	1996-03-12	4(5) substituted imidazoles and their preparation and use
EA001551B1 (ru)	2001-04-23	Бензонафтиридины в качестве бронхиальных терапевтических средств
SI9012429A (en)	1997-12-31	New chroman and thiochroman derivatives
LU86435A1 (fr)	1986-12-05	Nouveaux derives du morphinane et de la morphine,leur preparation,leur application comme medicaments et les compositions pharmaceutiques les contenant
HK1008962B (en)	1999-05-21	Substituted imidazole derivatives and their preparation and use
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