DD295840A5 - 1-ethylphenoxathiin-10, 10-dioxid, verfahren zu seiner herstellung und pharmazeutische zusammensetzung - Google Patents

1-ethylphenoxathiin-10, 10-dioxid, verfahren zu seiner herstellung und pharmazeutische zusammensetzung Download PDF

Info

Publication number: DD295840A5
Authority: DD; German Democratic Republic
Prior art keywords: dioxide; hydrogen; compound; ethylphenoxathiin; mao
Prior art date: 1989-09-18

Application number

DD90344071A

Other languages

German (de)

English (en)

Inventor

Morton Harfenist

Gee Daniel P C Mc

Helen L White

Barret R Cooper

Jonathan R T Davidson

Original Assignee

��@��@��@��k��

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.)

1989-09-18

Filing date

1990-09-17

Publication date

1991-11-14

1990-09-17 Application filed by ��@��@��@��k�� filed Critical ��@��@��@��k��

1991-11-14 Publication of DD295840A5 publication Critical patent/DD295840A5/de

Links

238000000034 method Methods 0.000 title claims description 30
239000008194 pharmaceutical composition Substances 0.000 title claims description 5
XJLRCPYQIPAQCA-UHFFFAOYSA-N phenoxathiine 10,10-dioxide Chemical compound C1=CC=C2S(=O)(=O)C3=CC=CC=C3OC2=C1 XJLRCPYQIPAQCA-UHFFFAOYSA-N 0.000 claims abstract description 20
238000006243 chemical reaction Methods 0.000 claims abstract description 13
-1 compound ethylphenoxathiin-10,10-dioxide Chemical class 0.000 claims abstract description 11
HQSRQKBSOOZLHH-UHFFFAOYSA-N 1-ethylphenoxathiine 10,10-dioxide Chemical compound O1C2=CC=CC=C2S(=O)(=O)C2=C1C=CC=C2CC HQSRQKBSOOZLHH-UHFFFAOYSA-N 0.000 claims abstract description 8
230000003647 oxidation Effects 0.000 claims abstract description 6
238000007254 oxidation reaction Methods 0.000 claims abstract description 6
230000009467 reduction Effects 0.000 claims abstract description 5
229910052739 hydrogen Inorganic materials 0.000 claims description 24
239000001257 hydrogen Substances 0.000 claims description 20
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 10
150000002431 hydrogen Chemical class 0.000 claims description 10
229910052736 halogen Inorganic materials 0.000 claims description 7
150000002367 halogens Chemical class 0.000 claims description 6
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 5
150000001721 carbon Chemical group 0.000 claims description 4
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 4
239000003054 catalyst Substances 0.000 claims description 4
GJSGGHOYGKMUPT-UHFFFAOYSA-N phenoxathiine Chemical compound C1=CC=C2OC3=CC=CC=C3SC2=C1 GJSGGHOYGKMUPT-UHFFFAOYSA-N 0.000 claims description 4
238000005984 hydrogenation reaction Methods 0.000 claims description 3
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PJLJUHYRWZCAJT-UHFFFAOYSA-N 1-ethylphenoxathiine Chemical compound O1C2=CC=CC=C2SC2=C1C=CC=C2CC PJLJUHYRWZCAJT-UHFFFAOYSA-N 0.000 abstract description 7
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241000699670 Mus sp. Species 0.000 description 1
PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 1
229910019142 PO4 Inorganic materials 0.000 description 1
206010033664 Panic attack Diseases 0.000 description 1
OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
229920002565 Polyethylene Glycol 400 Polymers 0.000 description 1
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
239000004809 Teflon Substances 0.000 description 1
229920006362 Teflon® Polymers 0.000 description 1
ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 1
238000006856 Wolf-Kishner-Huang Minlon reduction reaction Methods 0.000 description 1
238000005644 Wolff-Kishner reduction reaction Methods 0.000 description 1
HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
ZBIKORITPGTTGI-UHFFFAOYSA-N [acetyloxy(phenyl)-$l^{3}-iodanyl] acetate Chemical compound CC(=O)OI(OC(C)=O)C1=CC=CC=C1 ZBIKORITPGTTGI-UHFFFAOYSA-N 0.000 description 1
230000001476 alcoholic effect Effects 0.000 description 1
125000000217 alkyl group Chemical group 0.000 description 1
208000022531 anorexia Diseases 0.000 description 1
239000003963 antioxidant agent Substances 0.000 description 1
235000006708 antioxidants Nutrition 0.000 description 1
238000013459 approach Methods 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
239000012298 atmosphere Substances 0.000 description 1
238000010533 azeotropic distillation Methods 0.000 description 1
235000013361 beverage Nutrition 0.000 description 1
239000011230 binding agent Substances 0.000 description 1
230000000035 biogenic effect Effects 0.000 description 1
230000004071 biological effect Effects 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
239000012496 blank sample Substances 0.000 description 1
239000008280 blood Substances 0.000 description 1
210000004369 blood Anatomy 0.000 description 1
208000030963 borderline personality disease Diseases 0.000 description 1
229910052799 carbon Inorganic materials 0.000 description 1
150000001722 carbon compounds Chemical class 0.000 description 1
210000001715 carotid artery Anatomy 0.000 description 1
235000013351 cheese Nutrition 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
229940110456 cocoa butter Drugs 0.000 description 1
235000019868 cocoa butter Nutrition 0.000 description 1
238000004440 column chromatography Methods 0.000 description 1
230000002860 competitive effect Effects 0.000 description 1
238000007906 compression Methods 0.000 description 1
230000006835 compression Effects 0.000 description 1
238000000748 compression moulding Methods 0.000 description 1
231100000867 compulsive behavior Toxicity 0.000 description 1
238000013270 controlled release Methods 0.000 description 1
TVZPLCNGKSPOJA-UHFFFAOYSA-N copper zinc Chemical compound [Cu].[Zn] TVZPLCNGKSPOJA-UHFFFAOYSA-N 0.000 description 1
206010061428 decreased appetite Diseases 0.000 description 1
230000018044 dehydration Effects 0.000 description 1
238000006297 dehydration reaction Methods 0.000 description 1
230000003001 depressive effect Effects 0.000 description 1
238000000502 dialysis Methods 0.000 description 1
FAMRKDQNMBBFBR-BQYQJAHWSA-N diethyl azodicarboxylate Substances CCOC(=O)\N=N\C(=O)OCC FAMRKDQNMBBFBR-BQYQJAHWSA-N 0.000 description 1
IJKVHSBPTUYDLN-UHFFFAOYSA-N dihydroxy(oxo)silane Chemical compound O[Si](O)=O IJKVHSBPTUYDLN-UHFFFAOYSA-N 0.000 description 1
239000003085 diluting agent Substances 0.000 description 1
239000002270 dispersing agent Substances 0.000 description 1
239000006185 dispersion Substances 0.000 description 1
239000002552 dosage form Substances 0.000 description 1
229940079593 drug Drugs 0.000 description 1
239000003814 drug Substances 0.000 description 1
230000004064 dysfunction Effects 0.000 description 1
238000010828 elution Methods 0.000 description 1
FAMRKDQNMBBFBR-UHFFFAOYSA-N ethyl n-ethoxycarbonyliminocarbamate Chemical compound CCOC(=O)N=NC(=O)OCC FAMRKDQNMBBFBR-UHFFFAOYSA-N 0.000 description 1
238000002474 experimental method Methods 0.000 description 1
230000009969 flowable effect Effects 0.000 description 1
239000012362 glacial acetic acid Substances 0.000 description 1
239000011521 glass Substances 0.000 description 1
125000005456 glyceride group Chemical group 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 1
229940071870 hydroiodic acid Drugs 0.000 description 1
238000011065 in-situ storage Methods 0.000 description 1
238000011534 incubation Methods 0.000 description 1
239000003701 inert diluent Substances 0.000 description 1
230000002401 inhibitory effect Effects 0.000 description 1
230000002427 irreversible effect Effects 0.000 description 1
239000000644 isotonic solution Substances 0.000 description 1
238000002372 labelling Methods 0.000 description 1
229940041476 lactose 100 mg Drugs 0.000 description 1
239000012280 lithium aluminium hydride Substances 0.000 description 1
210000005228 liver tissue Anatomy 0.000 description 1
239000000314 lubricant Substances 0.000 description 1
230000007257 malfunction Effects 0.000 description 1
230000007246 mechanism Effects 0.000 description 1
125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 1
230000002438 mitochondrial effect Effects 0.000 description 1
238000000465 moulding Methods 0.000 description 1
239000002858 neurotransmitter agent Substances 0.000 description 1
239000007764 o/w emulsion Substances 0.000 description 1
239000003960 organic solvent Substances 0.000 description 1
150000002902 organometallic compounds Chemical class 0.000 description 1
239000007800 oxidant agent Substances 0.000 description 1
230000001590 oxidative effect Effects 0.000 description 1
229910052763 palladium Inorganic materials 0.000 description 1
208000019906 panic disease Diseases 0.000 description 1
238000007911 parenteral administration Methods 0.000 description 1
230000036961 partial effect Effects 0.000 description 1
239000008188 pellet Substances 0.000 description 1
208000022821 personality disease Diseases 0.000 description 1
239000003444 phase transfer catalyst 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
229910052698 phosphorus Inorganic materials 0.000 description 1
239000011574 phosphorus Substances 0.000 description 1
229910052697 platinum Inorganic materials 0.000 description 1
239000003880 polar aprotic solvent Substances 0.000 description 1
229920000151 polyglycol Polymers 0.000 description 1
239000010695 polyglycol Substances 0.000 description 1
208000028173 post-traumatic stress disease Diseases 0.000 description 1
229910052700 potassium Inorganic materials 0.000 description 1
239000011591 potassium Substances 0.000 description 1
229910000027 potassium carbonate Inorganic materials 0.000 description 1
229910000160 potassium phosphate Inorganic materials 0.000 description 1
235000011009 potassium phosphates Nutrition 0.000 description 1
LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
230000003389 potentiating effect Effects 0.000 description 1
238000011321 prophylaxis Methods 0.000 description 1
125000006239 protecting group Chemical group 0.000 description 1
239000003586 protic polar solvent Substances 0.000 description 1
239000001944 prunus armeniaca kernel oil Substances 0.000 description 1
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
CVHZOJJKTDOEJC-UHFFFAOYSA-N saccharin Chemical compound C1=CC=C2C(=O)NS(=O)(=O)C2=C1 CVHZOJJKTDOEJC-UHFFFAOYSA-N 0.000 description 1
150000003839 salts Chemical class 0.000 description 1
229920006395 saturated elastomer Polymers 0.000 description 1
MEZLKOACVSPNER-GFCCVEGCSA-N selegiline Chemical compound C#CCN(C)[C@H](C)CC1=CC=CC=C1 MEZLKOACVSPNER-GFCCVEGCSA-N 0.000 description 1
239000012279 sodium borohydride Substances 0.000 description 1
229910000033 sodium borohydride Inorganic materials 0.000 description 1
230000002269 spontaneous effect Effects 0.000 description 1
238000013222 sprague-dawley male rat Methods 0.000 description 1
229940071117 starch glycolate Drugs 0.000 description 1
239000004094 surface-active agent Substances 0.000 description 1
239000000375 suspending agent Substances 0.000 description 1
238000010189 synthetic method Methods 0.000 description 1
238000010998 test method Methods 0.000 description 1
239000002562 thickening agent Substances 0.000 description 1
YRHRIQCWCFGUEQ-UHFFFAOYSA-N thioxanthen-9-one Chemical class C1=CC=C2C(=O)C3=CC=CC=C3SC2=C1 YRHRIQCWCFGUEQ-UHFFFAOYSA-N 0.000 description 1
239000011135 tin Substances 0.000 description 1
231100000419 toxicity Toxicity 0.000 description 1
230000001988 toxicity Effects 0.000 description 1
229960003741 tranylcypromine Drugs 0.000 description 1
239000007762 w/o emulsion Substances 0.000 description 1
229910052725 zinc Inorganic materials 0.000 description 1
239000011701 zinc Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D327/00—Heterocyclic compounds containing rings having oxygen and sulfur atoms as the only ring hetero atoms
- C07D327/02—Heterocyclic compounds containing rings having oxygen and sulfur atoms as the only ring hetero atoms one oxygen atom and one sulfur atom
- C07D327/06—Six-membered rings
- C07D327/08—[b,e]-condensed with two six-membered carbocyclic rings
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/38—Heterocyclic compounds having sulfur as a ring hetero atom
- A61K31/39—Heterocyclic compounds having sulfur as a ring hetero atom having oxygen in the same ring
- 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
- A61P25/02—Drugs for disorders of the nervous system for peripheral neuropathies
- 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
- A61P25/24—Antidepressants
- 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
- A61P25/26—Psychostimulants, e.g. nicotine, cocaine

Landscapes

Health & Medical Sciences (AREA)
Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Pharmacology & Pharmacy (AREA)
Animal Behavior & Ethology (AREA)
Veterinary Medicine (AREA)
Public Health (AREA)
General Health & Medical Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
Medicinal Chemistry (AREA)
Biomedical Technology (AREA)
Neurosurgery (AREA)
Engineering & Computer Science (AREA)
General Chemical & Material Sciences (AREA)
Neurology (AREA)
Chemical Kinetics & Catalysis (AREA)
Bioinformatics & Cheminformatics (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Psychiatry (AREA)
Epidemiology (AREA)
Pain & Pain Management (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Medicinal Preparation (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

DD90344071A 1989-09-18 1990-09-17 1-ethylphenoxathiin-10, 10-dioxid, verfahren zu seiner herstellung und pharmazeutische zusammensetzung DD295840A5 (de)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
GB898921069A GB8921069D0 (en)	1989-09-18	1989-09-18	Pharmaceutically active compound,preparation and use

Publications (1)

Publication Number	Publication Date
DD295840A5 true DD295840A5 (de)	1991-11-14

Family

ID=10663238

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
DD90344071A DD295840A5 (de)	1989-09-18	1990-09-17	1-ethylphenoxathiin-10, 10-dioxid, verfahren zu seiner herstellung und pharmazeutische zusammensetzung

Country Status (18)

Country	Link
US (1)	US5420156A (fr)
EP (1)	EP0419157A3 (fr)
JP (1)	JPH03145486A (fr)
KR (1)	KR940000074B1 (fr)
AU (1)	AU643701B2 (fr)
CA (1)	CA2025524A1 (fr)
DD (1)	DD295840A5 (fr)
FI (1)	FI88794C (fr)
GB (1)	GB8921069D0 (fr)
HU (1)	HU207065B (fr)
IE (1)	IE903355A1 (fr)
IL (1)	IL95709A (fr)
MC (1)	MC2152A1 (fr)
MX (1)	MX9203221A (fr)
NO (1)	NO175746C (fr)
NZ (1)	NZ235343A (fr)
PT (1)	PT95327A (fr)
ZA (1)	ZA907398B (fr)

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
GB8921069D0 (en) *	1989-09-18	1989-11-01	Wellcome Found	Pharmaceutically active compound,preparation and use
IE913256A1 (en) *	1990-09-17	1992-02-25	Wellcome Found	Pharmacologically active compounds and use
ES2082723B1 (es) *	1994-07-20	1996-10-01	Lilly Sa	Formulacion farmaceutica de fluoxetina en forma dispersable.
AU5531798A (en) *	1996-09-11	1998-04-14	Krenitsky Pharmaceutical, Inc.	Pharmacologically active compounds and use

Family Cites Families (12)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US2997422A (en) *	1959-01-09	1961-08-22	Smith Kline French Lab	Monoamine oxidase inhibition
AU2843377A (en) *	1972-05-19	1979-03-08	Wellcome Found	Phenoxathiin dioxides
GB1447032A (en) *	1972-05-19	1976-08-25	Wellcome Found	Tricyclic sulphones and pharmaceutical compositions containing them
US4091108A (en) *	1972-09-06	1978-05-23	Burroughs Wellcome Co.	Antiallergic pharmaceutical composition and use
FR2239025B1 (fr) *	1973-07-25	1982-07-02	Souriau & Cie
DE2339617A1 (de) *	1973-08-04	1975-02-20	Merck Patent Gmbh	Sulfoxide und sulfone sowie verfahren zu ihrer herstellung
US4012517A (en) *	1975-01-24	1977-03-15	Burroughs Wellcome Co.	Compositions and treatment
EP0068563A3 (fr) *	1981-06-23	1983-06-15	THE PROCTER & GAMBLE COMPANY	Dérivés d'acide acétique hétérocycliques et compositions pour le traitement des affections osseuses
EP0150891A1 (fr) *	1984-01-05	1985-08-07	The Wellcome Foundation Limited	Composés tricycliques, procédés pour leur préparation, compositions les contenant et leur usage en médecine
EP0270252A3 (fr) *	1986-11-11	1990-04-04	Imperial Chemical Industries Plc	Dérivés d'acides propénoiques utilisés en agriculture
JPH01294718A (ja) *	1987-12-15	1989-11-28	Nippon Oil & Fats Co Ltd	新規な透明樹脂、高屈折率透明光学用樹脂、塗料用樹脂及び単量体
GB8921069D0 (en) *	1989-09-18	1989-11-01	Wellcome Found	Pharmaceutically active compound,preparation and use

1989
- 1989-09-18 GB GB898921069A patent/GB8921069D0/en active Pending
1990
- 1990-09-10 KR KR1019900014272A patent/KR940000074B1/ko not_active Expired - Fee Related
- 1990-09-17 PT PT95327A patent/PT95327A/pt not_active Application Discontinuation
- 1990-09-17 CA CA002025524A patent/CA2025524A1/fr not_active Abandoned
- 1990-09-17 NO NO904034A patent/NO175746C/no unknown
- 1990-09-17 MC MC902148A patent/MC2152A1/fr unknown
- 1990-09-17 NZ NZ235343A patent/NZ235343A/en unknown
- 1990-09-17 IL IL9570990A patent/IL95709A/en not_active IP Right Cessation
- 1990-09-17 EP EP19900310109 patent/EP0419157A3/en not_active Ceased
- 1990-09-17 HU HU905928A patent/HU207065B/hu not_active IP Right Cessation
- 1990-09-17 IE IE335590A patent/IE903355A1/en unknown
- 1990-09-17 ZA ZA907398A patent/ZA907398B/xx unknown
- 1990-09-17 JP JP2246932A patent/JPH03145486A/ja active Pending
- 1990-09-17 FI FI904560A patent/FI88794C/fi not_active IP Right Cessation
- 1990-09-17 DD DD90344071A patent/DD295840A5/de not_active IP Right Cessation
- 1990-09-18 AU AU62653/90A patent/AU643701B2/en not_active Ceased
1992
- 1992-06-24 MX MX9203221A patent/MX9203221A/es unknown
1993
- 1993-12-08 US US08/164,043 patent/US5420156A/en not_active Expired - Fee Related

Also Published As

Publication number	Publication date
NO175746C (no)	1994-11-30
JPH03145486A (ja)	1991-06-20
CA2025524A1 (fr)	1991-03-19
FI904560A0 (fi)	1990-09-17
EP0419157A2 (fr)	1991-03-27
HU207065B (en)	1993-03-01
FI88794C (fi)	1993-07-12
HU905928D0 (en)	1991-03-28
ZA907398B (en)	1992-05-27
FI88794B (fi)	1993-03-31
KR940000074B1 (ko)	1994-01-05
MX9203221A (es)	1992-07-01
KR910006270A (ko)	1991-04-29
PT95327A (pt)	1991-05-22
HUT58068A (en)	1992-01-28
NO904034L (no)	1991-03-19
AU6265390A (en)	1991-03-21
NO904034D0 (no)	1990-09-17
AU643701B2 (en)	1993-11-25
IL95709A (en)	1995-03-30
NO175746B (no)	1994-08-22
EP0419157A3 (en)	1991-08-28
GB8921069D0 (en)	1989-11-01
MC2152A1 (fr)	1992-03-10
IE903355A1 (en)	1991-04-10
NZ235343A (en)	1992-08-26
US5420156A (en)	1995-05-30

Legal Events

Date	Code	Title	Description
1997-06-05	ENJ	Ceased due to non-payment of renewal fee

Publication	Publication Date	Title
EP0163965B1 (fr)	1989-11-08	Pyridazinones, leur préparation et leur utilisation, médicaments contenant des pyridazinones
DE3522604A1 (de)	1987-01-08	Neue feste formen von 2-(gamma)thoxy-4-(n-(1-(2-piperidino-phenyl)-3-methyl-1-butyl)-aminocarbonylmethyl)-benzoesaeure, diese formen enthaltende arzneimittel und verfahren zu ihrer herstellung
DE2901477A1 (de)	1979-07-19	Thienohydantoinderivate und diese enthaltende arzneimittel
EP0148440A1 (fr)	1985-07-17	1,3,4,5-Tétrahydrobenzo(c,d)indoles, procédé de préparation et utilisation
EP0157267B1 (fr)	1988-11-23	Benzopyrannes substiués, procédé pour leur préparation et leur utilisation comme médicaments
DE69908421T2 (de)	2004-03-18	Pharmazeutische zusammensetzung enthaltend eine kombination der dextro- und laevo-isomeren von sotalol
WO1982000293A1 (fr)	1982-02-04	Derives substitues de l'adenosine-3',5'-phosphobenzyl-triester, procede de leur preparation et remedes contenant de tels composes
WO1999025716A9 (fr)	1999-09-02	Pyranones, leur procede de production et leur utilisation
DE2438399C3 (de)	1979-06-13	a-substituierte Benzhydrolderivate und ihre Salze, solche enthaltende Arzneimittel und Verfahren zur Herstellung derselben
DE2941869A1 (de)	1980-04-30	Dibenzothiepinderivate, verfahren zu ihrer herstellung und diese enthaltende arzneimittel
DD295840A5 (de)	1991-11-14	1-ethylphenoxathiin-10, 10-dioxid, verfahren zu seiner herstellung und pharmazeutische zusammensetzung
DE1470074C3 (de)	1974-01-24	1,2,3,4,6,7-Hexahydro-l lbH-benzo eckige Klammer auf a eckige Klammer zu chinolizine sowie deren Acetate und/oder phsiologisch verträgliche Säureadditionssalze sowie Verfahren zu ihrer Herstellung
DE1909406C3 (de)	1978-11-16	Tricyclische Verbindungen
EP0027268A2 (fr)	1981-04-22	Dérivés de la quinazoline, procédé et intermédiaires pour leur préparation, médicaments les contenant et leur application
EP0496274B1 (fr)	1996-07-03	Dérivé tricyclique de la pyridone
DE69021525T2 (de)	1996-03-21	Pyrrolaldehydderivate.
DD202158A5 (de)	1983-08-31	Verfahren zur herstellung von imidazolin-derivaten
DE2646213A1 (de)	1977-05-12	Aroylphenylnaphthaline und verfahren zu ihrer herstellung
DE3146867A1 (de)	1982-07-08	Aether von substituierten hydroxymethylpyrazinen
EP0024616B1 (fr)	1983-02-09	1-(3'-Acyloxyphényl)-2-aminoéthanols, leurs sels d'addition acides, compositions pharmaceutiques les contenant et procédé pour leur préparation
DE4405641C2 (de)	1997-04-30	Pharmazeutische Zusammensetzung, enthaltend 2-(4-Methoxyphenoxy)-3-pyridinamin
DD267978A5 (de)	1989-05-17	Verfahren zur herstellung von hydroxamsaeure-arylderivaten
DE2114230A1 (de)	1972-10-05	Psychotropes Praeparat und Verfahren zur Herstellung seines Wirkstoffes
AT353272B (de)	1979-11-12	Verfahren zur herstellung von neuen piperidin- derivaten sowie von deren salzen und optisch aktiven formen
EP0802181B1 (fr)	1999-12-22	Rétinoides