CH628633A5 - Esters of 1,4-ethano-10-hydroxy-5-oxo-5H-[1]benzopyrano[3,4-b]pyridine derivatives which can be used especially in the treatment of glaucoma - Google Patents

Esters of 1,4-ethano-10-hydroxy-5-oxo-5H-[1]benzopyrano[3,4-b]pyridine derivatives which can be used especially in the treatment of glaucoma Download PDF

Info

Publication number: CH628633A5
Authority: CH; Switzerland
Prior art keywords: compound; oxo; ethano; formula; hydrochloride
Prior art date: 1977-03-14

Application number

CH277878A

Other languages

English (en)

French (fr)

Inventor

David Lloyd Arendsen

Harold Elmer Zaugg

Original Assignee

Abbott Lab

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.)

1977-03-14

Filing date

1978-03-14

Publication date

1982-03-15

1978-03-14 Application filed by Abbott Lab filed Critical Abbott Lab

1982-03-15 Publication of CH628633A5 publication Critical patent/CH628633A5/fr

Links

208000010412 Glaucoma Diseases 0.000 title description 2
150000002148 esters Chemical class 0.000 title description 2
JTERYOBXUOMOKK-UHFFFAOYSA-N 4-hydroxy-9-oxa-12-azatetracyclo[10.2.2.02,11.03,8]hexadeca-1(14),2(11),3,5,7-pentaen-10-one Chemical class OC1=CC=CC2=C1C1=C(N3CC=C1CC3)C(O2)=O JTERYOBXUOMOKK-UHFFFAOYSA-N 0.000 title 1
150000001875 compounds Chemical class 0.000 description 35
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 16
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
239000000243 solution Substances 0.000 description 12
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 10
230000004410 intraocular pressure Effects 0.000 description 10
-1 1,2-dimethyl heptyl Chemical group 0.000 description 9
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 8
239000002253 acid Substances 0.000 description 8
239000007787 solid Substances 0.000 description 8
150000003839 salts Chemical class 0.000 description 7
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 6
QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 6
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 6
239000003814 drug Substances 0.000 description 6
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 5
238000004458 analytical method Methods 0.000 description 5
230000000694 effects Effects 0.000 description 5
239000012458 free base Substances 0.000 description 5
125000004432 carbon atom Chemical group C* 0.000 description 4
238000002329 infrared spectrum Methods 0.000 description 4
238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 4
229910052760 oxygen Inorganic materials 0.000 description 4
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 4
229910052717 sulfur Inorganic materials 0.000 description 4
UCTWMZQNUQWSLP-VIFPVBQESA-N (R)-adrenaline Chemical compound CNC[C@H](O)C1=CC=C(O)C(O)=C1 UCTWMZQNUQWSLP-VIFPVBQESA-N 0.000 description 3
ZPSJGADGUYYRKE-UHFFFAOYSA-N 2H-pyran-2-one Chemical compound O=C1C=CC=CO1 ZPSJGADGUYYRKE-UHFFFAOYSA-N 0.000 description 3
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 3
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
238000001990 intravenous administration Methods 0.000 description 3
229910052943 magnesium sulfate Inorganic materials 0.000 description 3
235000019341 magnesium sulphate Nutrition 0.000 description 3
238000000034 method Methods 0.000 description 3
239000000902 placebo Substances 0.000 description 3
229940068196 placebo Drugs 0.000 description 3
RZWZRACFZGVKFM-UHFFFAOYSA-N propanoyl chloride Chemical compound CCC(Cl)=O RZWZRACFZGVKFM-UHFFFAOYSA-N 0.000 description 3
239000003204 tranquilizing agent Substances 0.000 description 3
230000002936 tranquilizing effect Effects 0.000 description 3
QCHFTSOMWOSFHM-WPRPVWTQSA-N (+)-Pilocarpine Chemical compound C1OC(=O)[C@@H](CC)[C@H]1CC1=CN=CN1C QCHFTSOMWOSFHM-WPRPVWTQSA-N 0.000 description 2
229930182837 (R)-adrenaline Natural products 0.000 description 2
FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 2
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
QCHFTSOMWOSFHM-UHFFFAOYSA-N SJ000285536 Natural products C1OC(=O)C(CC)C1CC1=CN=CN1C QCHFTSOMWOSFHM-UHFFFAOYSA-N 0.000 description 2
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
229940079593 drug Drugs 0.000 description 2
229960005139 epinephrine Drugs 0.000 description 2
239000000706 filtrate Substances 0.000 description 2
239000007903 gelatin capsule Substances 0.000 description 2
125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
238000007918 intramuscular administration Methods 0.000 description 2
238000002844 melting Methods 0.000 description 2
230000008018 melting Effects 0.000 description 2
229960001416 pilocarpine Drugs 0.000 description 2
229960002139 pilocarpine hydrochloride Drugs 0.000 description 2
RNAICSBVACLLGM-GNAZCLTHSA-N pilocarpine hydrochloride Chemical compound Cl.C1OC(=O)[C@@H](CC)[C@H]1CC1=CN=CN1C RNAICSBVACLLGM-GNAZCLTHSA-N 0.000 description 2
239000011541 reaction mixture Substances 0.000 description 2
238000010992 reflux Methods 0.000 description 2
239000012047 saturated solution Substances 0.000 description 2
239000011780 sodium chloride Substances 0.000 description 2
229940125725 tranquilizer Drugs 0.000 description 2
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
ADFXKUOMJKEIND-UHFFFAOYSA-N 1,3-dicyclohexylurea Chemical compound C1CCCCC1NC(=O)NC1CCCCC1 ADFXKUOMJKEIND-UHFFFAOYSA-N 0.000 description 1
JVSFQJZRHXAUGT-UHFFFAOYSA-N 2,2-dimethylpropanoyl chloride Chemical compound CC(C)(C)C(Cl)=O JVSFQJZRHXAUGT-UHFFFAOYSA-N 0.000 description 1
KRAKRWDBAVVFAC-UHFFFAOYSA-N 2-chloro-3-methyloctane Chemical compound CCCCCC(C)C(C)Cl KRAKRWDBAVVFAC-UHFFFAOYSA-N 0.000 description 1
KBLUIEOCXFAGJQ-UHFFFAOYSA-N 4-morpholin-4-ylbutanoic acid;hydrobromide Chemical compound Br.OC(=O)CCCN1CCOCC1 KBLUIEOCXFAGJQ-UHFFFAOYSA-N 0.000 description 1
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
206010001488 Aggression Diseases 0.000 description 1
BTBUEUYNUDRHOZ-UHFFFAOYSA-N Borate Chemical compound [O-]B([O-])[O-] BTBUEUYNUDRHOZ-UHFFFAOYSA-N 0.000 description 1
241000282693 Cercopithecidae Species 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
FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
JVTAAEKCZFNVCJ-UHFFFAOYSA-M Lactate Chemical compound CC(O)C([O-])=O JVTAAEKCZFNVCJ-UHFFFAOYSA-M 0.000 description 1
241000124008 Mammalia Species 0.000 description 1
241001465754 Metazoa Species 0.000 description 1
241000283973 Oryctolagus cuniculus Species 0.000 description 1
229910019142 PO4 Inorganic materials 0.000 description 1
206010039424 Salivary hypersecretion Diseases 0.000 description 1
VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
229940022663 acetate Drugs 0.000 description 1
239000004480 active ingredient Substances 0.000 description 1
230000016571 aggressive behavior Effects 0.000 description 1
208000012761 aggressive behavior Diseases 0.000 description 1
229940040526 anhydrous sodium acetate Drugs 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 1
QAOWNCQODCNURD-UHFFFAOYSA-M bisulphate group Chemical group S([O-])(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-M 0.000 description 1
238000009530 blood pressure measurement Methods 0.000 description 1
239000006227 byproduct Substances 0.000 description 1
229940099340 desoxyn Drugs 0.000 description 1
POULHZVOKOAJMA-UHFFFAOYSA-M dodecanoate Chemical compound CCCCCCCCCCCC([O-])=O POULHZVOKOAJMA-UHFFFAOYSA-M 0.000 description 1
229960003072 epinephrine hydrochloride Drugs 0.000 description 1
229940070765 laurate Drugs 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
238000005259 measurement Methods 0.000 description 1
239000000155 melt Substances 0.000 description 1
TWXDDNPPQUTEOV-FVGYRXGTSA-N methamphetamine hydrochloride Chemical compound Cl.CN[C@@H](C)CC1=CC=CC=C1 TWXDDNPPQUTEOV-FVGYRXGTSA-N 0.000 description 1
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
239000000203 mixture Substances 0.000 description 1
239000012299 nitrogen atmosphere Substances 0.000 description 1
REEZZSHJLXOIHL-UHFFFAOYSA-N octanoyl chloride Chemical compound CCCCCCCC(Cl)=O REEZZSHJLXOIHL-UHFFFAOYSA-N 0.000 description 1
229940049964 oleate Drugs 0.000 description 1
ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 1
239000000546 pharmaceutical excipient Substances 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
235000015497 potassium bicarbonate Nutrition 0.000 description 1
229910000028 potassium bicarbonate Inorganic materials 0.000 description 1
239000011736 potassium bicarbonate Substances 0.000 description 1
TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
239000000843 powder Substances 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
238000002360 preparation method Methods 0.000 description 1
239000000047 product Substances 0.000 description 1
150000003222 pyridines Chemical class 0.000 description 1
208000026451 salivation Diseases 0.000 description 1
235000017557 sodium bicarbonate Nutrition 0.000 description 1
229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
239000012265 solid product Substances 0.000 description 1
238000001228 spectrum Methods 0.000 description 1
238000007619 statistical method Methods 0.000 description 1
239000008223 sterile water Substances 0.000 description 1
238000003756 stirring Methods 0.000 description 1
KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 1
229910021653 sulphate ion Inorganic materials 0.000 description 1
229940095064 tartrate Drugs 0.000 description 1
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
230000000699 topical effect Effects 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
ILWRPSCZWQJDMK-UHFFFAOYSA-N triethylazanium;chloride Chemical compound Cl.CCN(CC)CC ILWRPSCZWQJDMK-UHFFFAOYSA-N 0.000 description 1
229940070710 valerate Drugs 0.000 description 1
NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 1
238000005303 weighing Methods 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/12—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains three hetero rings
- C07D491/18—Bridged systems
- 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
- A61P25/20—Hypnotics; Sedatives
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P27/00—Drugs for disorders of the senses
- A61P27/02—Ophthalmic agents
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P27/00—Drugs for disorders of the senses
- A61P27/02—Ophthalmic agents
- A61P27/06—Antiglaucoma agents or miotics

Landscapes

Health & Medical Sciences (AREA)
Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Pharmacology & Pharmacy (AREA)
Animal Behavior & Ethology (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Engineering & Computer Science (AREA)
Ophthalmology & Optometry (AREA)
Life Sciences & Earth Sciences (AREA)
Bioinformatics & Cheminformatics (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Anesthesiology (AREA)
Biomedical Technology (AREA)
Neurology (AREA)
Neurosurgery (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)
Pyridine Compounds (AREA)

CH277878A 1977-03-14 1978-03-14 Esters of 1,4-ethano-10-hydroxy-5-oxo-5H-[1]benzopyrano[3,4-b]pyridine derivatives which can be used especially in the treatment of glaucoma CH628633A5 (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
US77775677A	1977-03-14	1977-03-14

Publications (1)

Publication Number	Publication Date
CH628633A5 true CH628633A5 (en)	1982-03-15

Family

ID=25111162

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CH277878A CH628633A5 (en)	1977-03-14	1978-03-14	Esters of 1,4-ethano-10-hydroxy-5-oxo-5H-[1]benzopyrano[3,4-b]pyridine derivatives which can be used especially in the treatment of glaucoma

Country Status (13)

Country	Link
JP (1)	JPS53130698A (da)
AU (1)	AU516613B2 (da)
CA (1)	CA1095519A (da)
CH (1)	CH628633A5 (da)
DE (1)	DE2810801A1 (da)
DK (1)	DK111378A (da)
FR (1)	FR2383948A1 (da)
GB (1)	GB1577304A (da)
GR (1)	GR65603B (da)
NO (1)	NO780880L (da)
PH (1)	PH13723A (da)
SE (1)	SE7802841L (da)
ZA (1)	ZA781074B (da)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
FR2645021A1 (fr) *	1989-03-30	1990-10-05	Sanofi Sa	Utilisation d'un agoniste potassique dans le traitement du glaucome
KR980008226A (ko) *	1996-07-05	1998-04-30	다케다 쿠니오	시각기능장애의 예방 및 치료제

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US3493579A (en) *	1967-05-29	1970-02-03	Little Inc A	1,4-ethano-5h-(1)benzopyrano (3,4-b)pyridines
US3905969A (en) *	1974-01-17	1975-09-16	Sharps Ass	Heterocyclic esters of 5H-{8 1{9 benzopyrano{8 3,4-b{9 pyridines

1978
- 1978-02-16 CA CA297,028A patent/CA1095519A/en not_active Expired
- 1978-02-23 ZA ZA00781074A patent/ZA781074B/xx unknown
- 1978-03-01 PH PH20839A patent/PH13723A/en unknown
- 1978-03-01 AU AU33718/78A patent/AU516613B2/en not_active Expired
- 1978-03-08 JP JP2554378A patent/JPS53130698A/ja active Pending
- 1978-03-10 GR GR55685A patent/GR65603B/el unknown
- 1978-03-13 SE SE7802841A patent/SE7802841L/xx unknown
- 1978-03-13 FR FR7807152A patent/FR2383948A1/fr active Granted
- 1978-03-13 NO NO780880A patent/NO780880L/no unknown
- 1978-03-13 DE DE19782810801 patent/DE2810801A1/de not_active Withdrawn
- 1978-03-13 GB GB9857/78A patent/GB1577304A/en not_active Expired
- 1978-03-13 DK DK111378A patent/DK111378A/da not_active Application Discontinuation
- 1978-03-14 CH CH277878A patent/CH628633A5/fr not_active IP Right Cessation

Also Published As

Publication number	Publication date
DK111378A (da)	1978-09-15
FR2383948A1 (fr)	1978-10-13
AU3371878A (en)	1979-09-06
AU516613B2 (en)	1981-06-11
CA1095519A (en)	1981-02-10
FR2383948B1 (da)	1981-07-31
SE7802841L (sv)	1978-09-15
GR65603B (en)	1980-10-14
DE2810801A1 (de)	1978-09-21
GB1577304A (en)	1980-10-22
ZA781074B (en)	1979-04-25
PH13723A (en)	1980-09-09
NO780880L (no)	1978-09-15
JPS53130698A (en)	1978-11-14

Legal Events

Date	Code	Title	Description
1984-11-30	PL	Patent ceased
2024-10-31	PL	Patent ceased

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DD298388A5 (de)	1992-02-20	Indenoindolverbindungen
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FR2669633A1 (fr)	1992-05-29	Nouveaux derives de la benzoselenazolinone, leur procede de preparation et les compositions pharmaceutiques qui les contiennent.
FR2565980A1 (fr)	1985-12-20	Nouveaux esters de 1,1-dioxydes de n-heteroaryl-4-hydroxy-2-methyl- 2h -1,2-benzothiazine- (ou thieno(2,3-e)-1,2-thiazine)-3-carboxamide precurseurs de medicaments et composition pharmaceutiques les contenant
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