NL8302013A - Optisch actieve n-aryloxazolidinon-2 verbindingen, die specifiek en omkeerbare remmende stoffen van mono-amino-oxydase van het type b zijn en werkwijze ter bereiding van deze verbindingen. - Google Patents

Optisch actieve n-aryloxazolidinon-2 verbindingen, die specifiek en omkeerbare remmende stoffen van mono-amino-oxydase van het type b zijn en werkwijze ter bereiding van deze verbindingen. Download PDF

Info

Publication number: NL8302013A
Authority: NL; Netherlands
Prior art keywords: formula; compound; compounds; sheet; formula sheet
Prior art date: 1982-06-08

Application number

NL8302013A

Other languages

English (en)

Dutch (nl)

Original Assignee

Delalande Sa

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.)

1982-06-08

Filing date

1983-06-06

Publication date

1984-01-02

1983-06-06 Application filed by Delalande Sa filed Critical Delalande Sa

1984-01-02 Publication of NL8302013A publication Critical patent/NL8302013A/nl

Links

150000001875 compounds Chemical class 0.000 title claims description 78
238000000034 method Methods 0.000 title claims description 9
230000002441 reversible effect Effects 0.000 title description 2
239000000203 mixture Substances 0.000 claims description 25
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 18
150000003839 salts Chemical class 0.000 claims description 13
239000002253 acid Substances 0.000 claims description 10
102000004316 Oxidoreductases Human genes 0.000 claims description 9
108090000854 Oxidoreductases Proteins 0.000 claims description 9
NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 claims description 9
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical group [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 claims description 8
238000003776 cleavage reaction Methods 0.000 claims description 7
-1 methylsulfonyloxy Chemical group 0.000 claims description 7
230000007017 scission Effects 0.000 claims description 7
BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 claims description 6
238000002360 preparation method Methods 0.000 claims description 6
239000003814 drug Substances 0.000 claims description 5
230000002401 inhibitory effect Effects 0.000 claims description 5
IWYDHOAUDWTVEP-UHFFFAOYSA-N R-2-phenyl-2-hydroxyacetic acid Natural products OC(=O)C(O)C1=CC=CC=C1 IWYDHOAUDWTVEP-UHFFFAOYSA-N 0.000 claims description 4
230000003197 catalytic effect Effects 0.000 claims description 4
229960002510 mandelic acid Drugs 0.000 claims description 4
230000003287 optical effect Effects 0.000 claims description 4
229910000027 potassium carbonate Inorganic materials 0.000 claims description 4
QBYIENPQHBMVBV-HFEGYEGKSA-N (2R)-2-hydroxy-2-phenylacetic acid Chemical compound O[C@@H](C(O)=O)c1ccccc1.O[C@@H](C(O)=O)c1ccccc1 QBYIENPQHBMVBV-HFEGYEGKSA-N 0.000 claims description 3
DDGRAFHHXYIQQR-UHFFFAOYSA-N 1-chloro-3-(chloromethyl)benzene Chemical compound ClCC1=CC=CC(Cl)=C1 DDGRAFHHXYIQQR-UHFFFAOYSA-N 0.000 claims description 3
238000009833 condensation Methods 0.000 claims description 3
230000005494 condensation Effects 0.000 claims description 3
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 3
125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 claims description 3
239000000010 aprotic solvent Substances 0.000 claims description 2
239000003937 drug carrier Substances 0.000 claims description 2
230000000269 nucleophilic effect Effects 0.000 claims description 2
239000008194 pharmaceutical composition Substances 0.000 claims description 2
238000004519 manufacturing process Methods 0.000 claims 3
239000000543 intermediate Substances 0.000 claims 2
CBOIHMRHGLHBPB-UHFFFAOYSA-N hydroxymethyl Chemical compound O[CH2] CBOIHMRHGLHBPB-UHFFFAOYSA-N 0.000 claims 1
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 30
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 19
QZAYGJVTTNCVMB-UHFFFAOYSA-N serotonin Chemical compound C1=C(O)C=C2C(CCN)=CNC2=C1 QZAYGJVTTNCVMB-UHFFFAOYSA-N 0.000 description 18
239000002244 precipitate Substances 0.000 description 12
238000002844 melting Methods 0.000 description 11
230000008018 melting Effects 0.000 description 11
239000000243 solution Substances 0.000 description 11
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 10
230000000694 effects Effects 0.000 description 10
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
AFVFQIVMOAPDHO-UHFFFAOYSA-N methanesulfonic acid Substances CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 8
BHHGXPLMPWCGHP-UHFFFAOYSA-N Phenethylamine Chemical compound NCCC1=CC=CC=C1 BHHGXPLMPWCGHP-UHFFFAOYSA-N 0.000 description 7
239000000706 filtrate Substances 0.000 description 7
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 6
IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 6
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 5
229940098779 methanesulfonic acid Drugs 0.000 description 5
239000000047 product Substances 0.000 description 5
229910052938 sodium sulfate Inorganic materials 0.000 description 5
235000011152 sodium sulphate Nutrition 0.000 description 5
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 4
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
241000700159 Rattus Species 0.000 description 3
239000004480 active ingredient Substances 0.000 description 3
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 3
239000002899 monoamine oxidase inhibitor Substances 0.000 description 3
239000012074 organic phase Substances 0.000 description 3
239000002904 solvent Substances 0.000 description 3
239000000725 suspension Substances 0.000 description 3
230000001225 therapeutic effect Effects 0.000 description 3
YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 description 2
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 group C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 2
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 2
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
238000003820 Medium-pressure liquid chromatography Methods 0.000 description 2
239000012359 Methanesulfonyl chloride Substances 0.000 description 2
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
230000001154 acute effect Effects 0.000 description 2
239000007864 aqueous solution Substances 0.000 description 2
125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 description 2
210000004556 brain Anatomy 0.000 description 2
229940079593 drug Drugs 0.000 description 2
238000000921 elemental analysis Methods 0.000 description 2
229910052739 hydrogen Inorganic materials 0.000 description 2
239000001257 hydrogen Substances 0.000 description 2
238000000338 in vitro Methods 0.000 description 2
QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 description 2
CQDGTJPVBWZJAZ-UHFFFAOYSA-N monoethyl carbonate Chemical compound CCOC(O)=O CQDGTJPVBWZJAZ-UHFFFAOYSA-N 0.000 description 2
229940076279 serotonin Drugs 0.000 description 2
239000000758 substrate Substances 0.000 description 2
239000003826 tablet Substances 0.000 description 2
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
206010020772 Hypertension Diseases 0.000 description 1
WTDRDQBEARUVNC-LURJTMIESA-N L-DOPA Chemical compound OC(=O)[C@@H](N)CC1=CC=C(O)C(O)=C1 WTDRDQBEARUVNC-LURJTMIESA-N 0.000 description 1
WTDRDQBEARUVNC-UHFFFAOYSA-N L-Dopa Natural products OC(=O)C(N)CC1=CC=C(O)C(O)=C1 WTDRDQBEARUVNC-UHFFFAOYSA-N 0.000 description 1
102000010909 Monoamine Oxidase Human genes 0.000 description 1
108010062431 Monoamine oxidase Proteins 0.000 description 1
101150030755 Ocln gene Proteins 0.000 description 1
208000018737 Parkinson disease Diseases 0.000 description 1
DZGWFCGJZKJUFP-UHFFFAOYSA-N Tyramine Natural products NCCC1=CC=C(O)C=C1 DZGWFCGJZKJUFP-UHFFFAOYSA-N 0.000 description 1
238000005903 acid hydrolysis reaction Methods 0.000 description 1
230000007059 acute toxicity Effects 0.000 description 1
231100000403 acute toxicity Toxicity 0.000 description 1
230000032683 aging Effects 0.000 description 1
229910021529 ammonia Inorganic materials 0.000 description 1
238000003556 assay Methods 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
208000015114 central nervous system disease Diseases 0.000 description 1
235000013351 cheese Nutrition 0.000 description 1
238000006243 chemical reaction Methods 0.000 description 1
238000004587 chromatography analysis Methods 0.000 description 1
238000010908 decantation Methods 0.000 description 1
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
239000003480 eluent Substances 0.000 description 1
238000002474 experimental method Methods 0.000 description 1
238000001914 filtration Methods 0.000 description 1
235000013305 food Nutrition 0.000 description 1
230000037406 food intake Effects 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
150000002431 hydrogen Chemical class 0.000 description 1
238000005984 hydrogenation reaction Methods 0.000 description 1
230000001631 hypertensive effect Effects 0.000 description 1
239000003112 inhibitor Substances 0.000 description 1
229940102223 injectable solution Drugs 0.000 description 1
238000002347 injection Methods 0.000 description 1
239000007924 injection Substances 0.000 description 1
239000007937 lozenge Substances 0.000 description 1
229920000609 methyl cellulose Polymers 0.000 description 1
239000001923 methylcellulose Substances 0.000 description 1
235000010981 methylcellulose Nutrition 0.000 description 1
230000007935 neutral effect Effects 0.000 description 1
230000000144 pharmacologic effect Effects 0.000 description 1
239000002574 poison Substances 0.000 description 1
231100000614 poison Toxicity 0.000 description 1
229940068886 polyethylene glycol 300 Drugs 0.000 description 1
229940068918 polyethylene glycol 400 Drugs 0.000 description 1
229960004063 propylene glycol Drugs 0.000 description 1
238000010992 reflux Methods 0.000 description 1
238000007363 ring formation reaction Methods 0.000 description 1
229920006395 saturated elastomer Polymers 0.000 description 1
239000000377 silicon dioxide Substances 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
238000004809 thin layer chromatography Methods 0.000 description 1
231100000816 toxic dose Toxicity 0.000 description 1
229960003732 tyramine Drugs 0.000 description 1
DZGWFCGJZKJUFP-UHFFFAOYSA-O tyraminium Chemical compound [NH3+]CCC1=CC=C(O)C=C1 DZGWFCGJZKJUFP-UHFFFAOYSA-O 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
- C07D263/02—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings
- C07D263/08—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D263/16—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D263/18—Oxygen atoms
- C07D263/20—Oxygen atoms attached in position 2
- 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
- C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
- C07D263/02—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings
- C07D263/08—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D263/16—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D263/18—Oxygen atoms
- C07D263/20—Oxygen atoms attached in position 2
- C07D263/24—Oxygen atoms attached in position 2 with hydrocarbon radicals, substituted by oxygen atoms, attached to other ring carbon atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
- C07D317/10—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings
- C07D317/14—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D317/28—Radicals substituted by nitrogen atoms

Landscapes

Organic Chemistry (AREA)
Chemical & Material Sciences (AREA)
Health & Medical Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
General Health & Medical Sciences (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Pharmacology & Pharmacy (AREA)
Engineering & Computer Science (AREA)
Animal Behavior & Ethology (AREA)
Bioinformatics & Cheminformatics (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Enzymes And Modification Thereof (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)

NL8302013A 1982-06-08 1983-06-06 Optisch actieve n-aryloxazolidinon-2 verbindingen, die specifiek en omkeerbare remmende stoffen van mono-amino-oxydase van het type b zijn en werkwijze ter bereiding van deze verbindingen. NL8302013A (nl)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
FR8209972		1982-06-08
FR8209972A FR2528046B1 (fr)	1982-06-08	1982-06-08	Derives de l'oxazolidinone-2 n-arylee optiquement actifs, inhibiteurs specifiques et reversibles de la monoamine oxydase de type b et leur procede de preparation

Publications (1)

Publication Number	Publication Date
NL8302013A true NL8302013A (nl)	1984-01-02

Family

ID=9274766

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NL8302013A NL8302013A (nl)	1982-06-08	1983-06-06	Optisch actieve n-aryloxazolidinon-2 verbindingen, die specifiek en omkeerbare remmende stoffen van mono-amino-oxydase van het type b zijn en werkwijze ter bereiding van deze verbindingen.

Country Status (13)

Country	Link
US (1)	US4598084A (fr)
JP (1)	JPS5980668A (fr)
AU (1)	AU1546283A (fr)
BE (1)	BE896972A (fr)
CH (3)	CH661507A5 (fr)
DE (1)	DE3320394A1 (fr)
FR (1)	FR2528046B1 (fr)
GB (3)	GB2121413B (fr)
IT (1)	IT1164269B (fr)
LU (1)	LU84851A1 (fr)
NL (1)	NL8302013A (fr)
SE (2)	SE8303136L (fr)
ZA (1)	ZA834119B (fr)

Families Citing this family (11)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JPS60241893A (ja) *	1984-05-15	1985-11-30	Kanegafuchi Chem Ind Co Ltd	光学活性（ｓ）―オキサゾリジノン誘導体の製造方法
DE3525648A1 (de) *	1985-07-18	1987-01-29	Bokel Heinz Hermann Dr	1-oxa-2-oxo-2-r-3-aza-5-z-cyclopentanderivate
FR2609029B1 (fr) *	1986-12-30	1989-12-08	Delalande Sa	Derives 5-aminoethyles de l'oxazolidinone-2, leur procede de preparation et leur application en therapeutique
US4897409A (en) *	1986-09-03	1990-01-30	Delalande S.A.	5-aminoethyloxazolidin-2-one derivatives
FR2603279B1 (fr) *	1986-09-03	1988-12-16	Rech Ind	Benzyloxy-phenyl-oxazolidinones, procede de preparation et utilisation en therapeutique
FR2626877B1 (fr) *	1988-02-05	1991-04-05	Delalande Sa	Ethers alkyliques ou benzyliques du phenol, leurs procedes de preparation et leur application en therapeutique
US5235063A (en) *	1989-10-17	1993-08-10	Delalande S.A.	Process of preparing by condensation certain
US5196543A (en) *	1989-10-17	1993-03-23	Delalande S.A.	3-aryloxazolidinone derivatives, process for their preparation and their use in therapy
AU2295792A (en) *	1991-06-26	1993-01-25	Sepracor, Inc.	Method and compositions for treating emesis, nausea and other disorders using optically pure r(+) ondansetron
AU3147593A (en) *	1991-11-26	1993-06-28	Sepracor, Inc.	Methods and compositions for treating hypertension, angina and other disorders using optically pure (-) amlodipine
CA2371822A1 (fr)	1999-03-01	2000-09-08	Sepracor Inc.	Procedes de traitement de l'apnee et de troubles de l'apnee a l'aide de r(+) ondansetron optiquement pur

Family Cites Families (5)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
FR2356422A1 (fr) *	1976-03-01	1978-01-27	Delalande Sa	Nouveaux hydroxymethyl-5 oxazolidinone-2, leur procede de preparation et leur application en therapeutique
FR2380780A2 (fr) *	1977-02-22	1978-09-15	Delalande Sa	Application en therapeutique des hydroxymethyl-5 oxazolidinones-2, notamment comme antidepresseurs
LU80081A1 (fr) *	1977-08-26	1979-05-15	Delalande Sa	Nouvelles hydroxymethyl-5 oxazolidinones-2,leur procede de preparation et leur application therapeutique
US4348393A (en) *	1978-06-09	1982-09-07	Delalande S.A.	N-Aryl oxazolidinones, oxazolidinethiones, pyrrolidinones, pyrrolidines and thiazolidinones
FR2428032A1 (fr) *	1978-06-09	1980-01-04	Delalande Sa	Nouvelles oxazolidimones, oxazolidinethiones et pyrrolidinones, leur procede de preparation et leur application en therapeutique

1982
- 1982-06-08 FR FR8209972A patent/FR2528046B1/fr not_active Expired
1983
- 1983-05-27 CH CH632/86A patent/CH661507A5/fr not_active IP Right Cessation
- 1983-05-27 CH CH633/86A patent/CH661500A5/fr not_active IP Right Cessation
- 1983-05-27 CH CH2900/83A patent/CH657362A5/fr not_active IP Right Cessation
- 1983-06-03 US US06/500,682 patent/US4598084A/en not_active Expired - Fee Related
- 1983-06-03 SE SE8303136A patent/SE8303136L/xx not_active Application Discontinuation
- 1983-06-06 NL NL8302013A patent/NL8302013A/nl not_active Application Discontinuation
- 1983-06-06 BE BE0/210943A patent/BE896972A/fr not_active IP Right Cessation
- 1983-06-06 GB GB08315433A patent/GB2121413B/en not_active Expired
- 1983-06-06 DE DE3320394A patent/DE3320394A1/de not_active Ceased
- 1983-06-07 IT IT21497/83A patent/IT1164269B/it active
- 1983-06-07 AU AU15462/83A patent/AU1546283A/en not_active Abandoned
- 1983-06-07 LU LU84851A patent/LU84851A1/fr unknown
- 1983-06-07 ZA ZA834119A patent/ZA834119B/xx unknown
- 1983-06-08 JP JP58102526A patent/JPS5980668A/ja active Pending
1985
- 1985-05-13 GB GB08512019A patent/GB2157692B/en not_active Expired
- 1985-05-13 GB GB08512020A patent/GB2157693B/en not_active Expired
1988
- 1988-06-17 SE SE8802281A patent/SE8802281D0/xx not_active Application Discontinuation

Also Published As

Publication number	Publication date
SE8802281L (sv)	1988-06-17
GB2157692A (en)	1985-10-30
CH657362A5 (fr)	1986-08-29
GB8512020D0 (en)	1985-06-19
FR2528046B1 (fr)	1985-06-21
AU1546283A (en)	1983-12-15
LU84851A1 (fr)	1985-03-29
GB2157693B (en)	1986-05-08
GB8512019D0 (en)	1985-06-19
BE896972A (fr)	1983-12-06
SE8303136D0 (sv)	1983-06-03
JPS5980668A (ja)	1984-05-10
SE8303136L (sv)	1983-12-09
IT8321497A0 (it)	1983-06-07
SE8802281D0 (sv)	1988-06-17
GB2121413B (en)	1986-05-08
IT1164269B (it)	1987-04-08
DE3320394A1 (de)	1983-12-08
CH661500A5 (fr)	1987-07-31
US4598084A (en)	1986-07-01
GB2121413A (en)	1983-12-21
GB2157692B (en)	1986-05-08
FR2528046A1 (fr)	1983-12-09
GB8315433D0 (en)	1983-07-13
GB2157693A (en)	1985-10-30
CH661507A5 (fr)	1987-07-31
ZA834119B (en)	1984-03-28

Legal Events

Date	Code	Title	Description
1985-01-01	A85	Still pending on 85-01-01
1990-02-01	BV	The patent application has lapsed

Publication	Publication Date	Title
EP0099789B1 (fr)	1987-07-29	Nouveaux dérivés de l'amino-3 quinuclidine, leur procédé de préperation et leur application en thérapeutique
LU83963A1 (fr)	1983-09-02	Nouveaux derives aminomethyl-5 oxazolidiniques,leur procede de preparation et leur application en therapeutique
NL8302013A (nl)	1984-01-02	Optisch actieve n-aryloxazolidinon-2 verbindingen, die specifiek en omkeerbare remmende stoffen van mono-amino-oxydase van het type b zijn en werkwijze ter bereiding van deze verbindingen.
EP0165919A1 (fr)	1985-12-27	(R)-alpha-éthyl-2-oxo-1-pyrrolidineacétamide
JPS6136259A (ja)	1986-02-20	新規オキシインドール‐誘導体、その製法及びこれを含有する心蔵及び循環系疾病の治療及び予防剤
EP0010029A2 (fr)	1980-04-16	Ellipticines substituées en position 1 par une chaîne polyaminée, leur synthèse et médicaments les contenant
MC1982A1 (fr)	1989-11-23	Procede de preparation de derives de la didesoxycitidine
FR2548666A1 (fr)	1985-01-11	Nouveaux derives du nor-tropane et du granatane, leur procede de preparation et leur application en therapeutique
FR2482965A1 (fr)	1981-11-27	1-(4-chlorobenzhydryl)-4-(2,3-dihydroxypropyl)-piperazine, son procede de preparation et son application en therapeutique
FR2672213A1 (fr)	1992-08-07	Utilisation de derives 4-(3-trifluoromethylphenyl)-1,2,3,6-tetrahydropyridiniques comme capteurs de radicaux libres.
CA1131230A (fr)	1982-09-07	Procede de preparation de nouveaux derives de 1,3-dihydro3-/1-/2-(2,3-dihydro 1,4-benzodioxin-2-yl) 2-hydroxy-ethyl/piperidin-4-yl/2h-indol-2-one
BE1009852A3 (fr)	1997-10-07	Derives 1-[2(vinyl-substitues)]-3-4-dihydro-5h-2,3-benzodiazepine.
EP0364350B1 (fr)	1994-01-12	Dérivés de méthyl-4[(phényl-4 pipérazinyl-1)-2 éthyl]-5 thiazole, leur procédé de préparation et les compositions pharmaceutiques en contenant
JPS6168473A (ja)	1986-04-08	ベンズイミダゾール誘導体
EP0074903B1 (fr)	1986-11-05	Dérivés d'amino-2 tétrahydro-1,2,3,4 naphtalène, leur préparation et leur application en thérapeutique
MC1357A1 (fr)	1981-08-10	Derives de 2,3-indoledione
FR2570701A1 (fr)	1986-03-28	Derives de furo(3,2-c)pyridines, leur preparation et leur application en therapeutique
EP0112252B1 (fr)	1990-02-07	Enantiomères lévogyres des dérivés de la tétrahydro-5,6,13,13a 8H-dibenzo(a, g)quinolizine, procédés d'obtention, compositions pharmaceutiques les contenant et application
BE1003519A3 (fr)	1992-04-14	Nouveaux derives de la carbonyl-2 n,n'-di-(trimethoxybenzoyle) piperazine, un procede pour leur preparation et compositions therapeutiques en contenant.
EP1192152B1 (fr)	2002-11-27	Nouveaux derives benzodioxanne imidazolines fluores, leur preparation et leurs applications en therapeutique
WO2003035663A1 (fr)	2003-05-01	Nouveaux derives d'hydroxyalkyle indolocarbazole, leur procede de preparation et les compositions pharmaceutiques qui les contiennent
EP0322391B1 (fr)	1992-03-25	Nouveaux dérivés de la phénylalkylamine
JPS60204799A (ja)	1985-10-16	カルボキシアルキルジペプチド誘導体およびそれらの製法
EP0235043B1 (fr)	1991-01-23	Dérivés de tétrahydrobenz (c,d) indole, leurs sels, procédé de préparation, application à titre de médicaments, compositions les renfermant et intermédiaires
EP0356323A1 (fr)	1990-02-28	Dérivés de benzopyrrolidinone, leur procédé de préparation et les compositions pharmaceutiques les renfermant