DD145754A5 - Verfahren zur herstellung von estern aus methyl-1 piperidinol-4 - Google Patents

Verfahren zur herstellung von estern aus methyl-1 piperidinol-4 Download PDF

Info

Publication number: DD145754A5
Authority: DD; German Democratic Republic
Prior art keywords: methyl; piperidinol; esters; quinolyl; treatment
Prior art date: 1978-09-01

Application number

DD79215307A

Other languages

German (de)

English (en)

Inventor

Laszlo Beregi

Pierre Hugon

Jacques Bure

Francoise Degrand

Original Assignee

Science Union & Cie

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.)

1978-09-01

Filing date

1979-08-31

Publication date

1981-01-07

1979-08-31 Application filed by Science Union & Cie filed Critical Science Union & Cie

1981-01-07 Publication of DD145754A5 publication Critical patent/DD145754A5/de

Links

238000000034 method Methods 0.000 title claims description 15
150000003839 salts Chemical class 0.000 claims description 8
238000002360 preparation method Methods 0.000 claims description 7
239000002253 acid Substances 0.000 claims description 4
150000007513 acids Chemical class 0.000 claims description 4
150000002148 esters Chemical class 0.000 claims description 4
239000000047 product Substances 0.000 description 12
150000001875 compounds Chemical class 0.000 description 9
210000000988 bone and bone Anatomy 0.000 description 8
101000588924 Anthopleura elegantissima Delta-actitoxin-Ael1a Proteins 0.000 description 7
230000005764 inhibitory process Effects 0.000 description 7
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206010061218 Inflammation Diseases 0.000 description 5
230000003110 anti-inflammatory effect Effects 0.000 description 5
230000004054 inflammatory process Effects 0.000 description 5
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
230000000694 effects Effects 0.000 description 4
230000007170 pathology Effects 0.000 description 4
229960002895 phenylbutazone Drugs 0.000 description 4
VYMDGNCVAMGZFE-UHFFFAOYSA-N phenylbutazonum Chemical compound O=C1C(CCCC)C(=O)N(C=2C=CC=CC=2)N1C1=CC=CC=C1 VYMDGNCVAMGZFE-UHFFFAOYSA-N 0.000 description 4
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
208000002193 Pain Diseases 0.000 description 3
208000038016 acute inflammation Diseases 0.000 description 3
230000006022 acute inflammation Effects 0.000 description 3
230000000202 analgesic effect Effects 0.000 description 3
208000037976 chronic inflammation Diseases 0.000 description 3
230000006020 chronic inflammation Effects 0.000 description 3
239000003814 drug Substances 0.000 description 3
238000002844 melting Methods 0.000 description 3
230000008018 melting Effects 0.000 description 3
230000000144 pharmacologic effect Effects 0.000 description 3
-1 4-piperidyl Chemical group 0.000 description 2
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
241000699666 Mus <mouse, genus> Species 0.000 description 2
206010028391 Musculoskeletal Pain Diseases 0.000 description 2
206010030113 Oedema Diseases 0.000 description 2
102000012404 Orosomucoid Human genes 0.000 description 2
108010061952 Orosomucoid Proteins 0.000 description 2
SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 2
208000025747 Rheumatic disease Diseases 0.000 description 2
208000007613 Shoulder Pain Diseases 0.000 description 2
201000002661 Spondylitis Diseases 0.000 description 2
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
230000001154 acute effect Effects 0.000 description 2
206010003246 arthritis Diseases 0.000 description 2
230000001684 chronic effect Effects 0.000 description 2
230000003412 degenerative effect Effects 0.000 description 2
229940079593 drug Drugs 0.000 description 2
230000002757 inflammatory effect Effects 0.000 description 2
SUMDYPCJJOFFON-UHFFFAOYSA-N isethionic acid Chemical compound OCCS(O)(=O)=O SUMDYPCJJOFFON-UHFFFAOYSA-N 0.000 description 2
210000003734 kidney Anatomy 0.000 description 2
HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
239000000203 mixture Substances 0.000 description 2
ZWLPBLYKEWSWPD-UHFFFAOYSA-N o-toluic acid Chemical compound CC1=CC=CC=C1C(O)=O ZWLPBLYKEWSWPD-UHFFFAOYSA-N 0.000 description 2
230000001354 painful effect Effects 0.000 description 2
239000008194 pharmaceutical composition Substances 0.000 description 2
BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 2
238000006722 reduction reaction Methods 0.000 description 2
239000002904 solvent Substances 0.000 description 2
239000000126 substance Substances 0.000 description 2
238000001356 surgical procedure Methods 0.000 description 2
230000006384 traumatic process Effects 0.000 description 2
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
RLQZIECDMISZHS-UHFFFAOYSA-N 2-phenylcyclohexa-2,5-diene-1,4-dione Chemical compound O=C1C=CC(=O)C(C=2C=CC=CC=2)=C1 RLQZIECDMISZHS-UHFFFAOYSA-N 0.000 description 1
BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
ALYNCZNDIQEVRV-UHFFFAOYSA-N 4-aminobenzoic acid Chemical compound NC1=CC=C(C(O)=O)C=C1 ALYNCZNDIQEVRV-UHFFFAOYSA-N 0.000 description 1
GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 description 1
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
229920000742 Cotton Polymers 0.000 description 1
239000001856 Ethyl cellulose Substances 0.000 description 1
ZZSNKZQZMQGXPY-UHFFFAOYSA-N Ethyl cellulose Chemical compound CCOCC1OC(OC)C(OCC)C(OCC)C1OC1C(O)C(O)C(OC)C(CO)O1 ZZSNKZQZMQGXPY-UHFFFAOYSA-N 0.000 description 1
WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 1
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 1
241000699670 Mus sp. Species 0.000 description 1
208000007101 Muscle Cramp Diseases 0.000 description 1
206010028980 Neoplasm Diseases 0.000 description 1
206010036030 Polyarthritis Diseases 0.000 description 1
208000005392 Spasm Diseases 0.000 description 1
229920002472 Starch Polymers 0.000 description 1
239000004480 active ingredient Substances 0.000 description 1
239000013543 active substance Substances 0.000 description 1
125000003545 alkoxy group Chemical group 0.000 description 1
125000000217 alkyl group Chemical group 0.000 description 1
229940064734 aminobenzoate Drugs 0.000 description 1
230000001760 anti-analgesic effect Effects 0.000 description 1
230000001773 anti-convulsant effect Effects 0.000 description 1
229940121363 anti-inflammatory agent Drugs 0.000 description 1
239000002260 anti-inflammatory agent Substances 0.000 description 1
239000001961 anticonvulsive agent Substances 0.000 description 1
229960003965 antiepileptics Drugs 0.000 description 1
WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
210000000481 breast Anatomy 0.000 description 1
239000003054 catalyst Substances 0.000 description 1
238000010531 catalytic reduction reaction Methods 0.000 description 1
238000006243 chemical reaction Methods 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
238000001816 cooling Methods 0.000 description 1
239000012043 crude product Substances 0.000 description 1
125000003963 dichloro group Chemical group Cl* 0.000 description 1
239000012153 distilled water Substances 0.000 description 1
230000000773 effect on pain Effects 0.000 description 1
235000019441 ethanol Nutrition 0.000 description 1
229920001249 ethyl cellulose Polymers 0.000 description 1
235000019325 ethyl cellulose Nutrition 0.000 description 1
229910052731 fluorine Inorganic materials 0.000 description 1
239000011737 fluorine Substances 0.000 description 1
239000008103 glucose Substances 0.000 description 1
230000003179 granulation Effects 0.000 description 1
238000005469 granulation Methods 0.000 description 1
229910052736 halogen Inorganic materials 0.000 description 1
150000002367 halogens Chemical class 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
208000012285 hip pain Diseases 0.000 description 1
238000010562 histological examination Methods 0.000 description 1
229910052739 hydrogen Inorganic materials 0.000 description 1
239000001257 hydrogen Substances 0.000 description 1
210000004969 inflammatory cell Anatomy 0.000 description 1
229940045996 isethionic acid Drugs 0.000 description 1
235000015110 jellies Nutrition 0.000 description 1
239000008101 lactose Substances 0.000 description 1
231100000053 low toxicity Toxicity 0.000 description 1
235000019359 magnesium stearate Nutrition 0.000 description 1
229910052943 magnesium sulfate Inorganic materials 0.000 description 1
235000019341 magnesium sulphate Nutrition 0.000 description 1
238000002483 medication Methods 0.000 description 1
229940098779 methanesulfonic acid Drugs 0.000 description 1
201000008383 nephritis Diseases 0.000 description 1
239000002674 ointment Substances 0.000 description 1
239000012044 organic layer Substances 0.000 description 1
239000005416 organic matter Substances 0.000 description 1
239000006187 pill Substances 0.000 description 1
229910052697 platinum Inorganic materials 0.000 description 1
208000030428 polyarticular arthritis Diseases 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
125000005493 quinolyl group Chemical group 0.000 description 1
238000001953 recrystallisation Methods 0.000 description 1
238000010992 reflux Methods 0.000 description 1
206010039073 rheumatoid arthritis Diseases 0.000 description 1
230000009291 secondary effect Effects 0.000 description 1
239000011734 sodium Substances 0.000 description 1
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239000008107 starch Substances 0.000 description 1
239000007858 starting material Substances 0.000 description 1
229940032330 sulfuric acid Drugs 0.000 description 1
239000000829 suppository Substances 0.000 description 1
239000000454 talc Substances 0.000 description 1
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238000002560 therapeutic procedure Methods 0.000 description 1
231100000331 toxic Toxicity 0.000 description 1
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231100000419 toxicity Toxicity 0.000 description 1
230000001988 toxicity Effects 0.000 description 1
239000003643 water by type Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
- 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
- A61P25/04—Centrally acting analgesics, e.g. opioids
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]

Landscapes

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

DD79215307A 1978-09-01 1979-08-31 Verfahren zur herstellung von estern aus methyl-1 piperidinol-4 DD145754A5 (de)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
CH922978		1978-09-01

Publications (1)

Publication Number	Publication Date
DD145754A5 true DD145754A5 (de)	1981-01-07

Family

ID=4349742

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
DD79215307A DD145754A5 (de)	1978-09-01	1979-08-31	Verfahren zur herstellung von estern aus methyl-1 piperidinol-4

Country Status (18)

Country	Link
US (1)	US4259335A (fr)
JP (1)	JPS5535087A (fr)
AR (1)	AR219814A1 (fr)
AU (1)	AU5048479A (fr)
BE (1)	BE878557A (fr)
CA (1)	CA1123830A (fr)
DD (1)	DD145754A5 (fr)
DE (1)	DE2935329A1 (fr)
ES (1)	ES483463A1 (fr)
FR (1)	FR2434808A1 (fr)
GB (1)	GB2031412B (fr)
IL (1)	IL58154A0 (fr)
IT (1)	IT7950135A0 (fr)
NL (1)	NL7906542A (fr)
OA (1)	OA06331A (fr)
PT (1)	PT70138A (fr)
SE (1)	SE7907251L (fr)
ZA (1)	ZA794631B (fr)

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JPS57155953A (en) *	1981-03-19	1982-09-27	Snow Brand Milk Prod Co Ltd	Preparation of frozen food having transparent ice shell
FR2503163A1 (fr) *	1981-04-03	1982-10-08	Roussel Uclaf	Nouveaux derives de l'acide 3-/4-quinoleinyl-amino/2-thiophene carboxylique, leur procede de preparation et leur application comme medicament
NZ202320A (en) *	1981-11-14	1985-05-31	Recordati Chem Pharm	Anthraniloyloxyalkanoates and pharmaceutical compositions containing such

Family Cites Families (6)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
NL131732C (fr) *	1966-03-31
FR6493M (fr) *	1967-06-29	1968-11-25
FR7870M (fr) *	1968-11-08	1970-04-27
US3579520A (en) *	1969-08-21	1971-05-18	Sterling Drug Inc	4-(4-piperidinyl-methyl or -1-ethyl) amino-7-chloroquinolines
US3971789A (en) *	1972-10-21	1976-07-27	John Wyeth & Brother Limited	O-(4-Quinolylamino)benzamides
FR2233059B1 (fr) *	1973-06-13	1976-09-03	Roussel Uclaf

1979
- 1979-08-01 FR FR7919760A patent/FR2434808A1/fr active Granted
- 1979-08-03 CA CA333,161A patent/CA1123830A/fr not_active Expired
- 1979-08-06 US US06/064,091 patent/US4259335A/en not_active Expired - Lifetime
- 1979-08-17 ES ES483463A patent/ES483463A1/es not_active Expired
- 1979-08-31 AR AR277918A patent/AR219814A1/es active
- 1979-08-31 ZA ZA00794631A patent/ZA794631B/xx unknown
- 1979-08-31 GB GB7930274A patent/GB2031412B/en not_active Expired
- 1979-08-31 PT PT70138A patent/PT70138A/fr unknown
- 1979-08-31 AU AU50484/79A patent/AU5048479A/en not_active Abandoned
- 1979-08-31 DD DD79215307A patent/DD145754A5/de unknown
- 1979-08-31 NL NL7906542A patent/NL7906542A/nl not_active Application Discontinuation
- 1979-08-31 JP JP11053179A patent/JPS5535087A/ja active Pending
- 1979-08-31 BE BE0/196985A patent/BE878557A/fr unknown
- 1979-08-31 OA OA56890A patent/OA06331A/fr unknown
- 1979-08-31 IT IT7950135A patent/IT7950135A0/it unknown
- 1979-08-31 DE DE19792935329 patent/DE2935329A1/de not_active Withdrawn
- 1979-08-31 SE SE7907251A patent/SE7907251L/ not_active Application Discontinuation
- 1979-08-31 IL IL58154A patent/IL58154A0/xx unknown

Also Published As

Publication number	Publication date
FR2434808A1 (fr)	1980-03-28
NL7906542A (nl)	1980-03-04
AR219814A1 (es)	1980-09-15
ZA794631B (en)	1980-08-27
GB2031412B (en)	1982-09-15
ES483463A1 (es)	1980-04-16
GB2031412A (en)	1980-04-23
FR2434808B1 (fr)	1983-12-23
BE878557A (fr)	1980-02-29
SE7907251L (sv)	1980-03-02
OA06331A (fr)	1981-06-30
IL58154A0 (en)	1979-12-30
US4259335A (en)	1981-03-31
JPS5535087A (en)	1980-03-11
PT70138A (fr)	1979-09-01
IT7950135A0 (it)	1979-08-31
AU5048479A (en)	1980-03-06
DE2935329A1 (de)	1980-03-20
CA1123830A (fr)	1982-05-18

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DE2634288B2 (fr)	1979-06-28
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DD143254A5 (de)	1980-08-13	Verfahren zur herstellung von tetrahydroisochinolin-derivaten
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DD145754A5 (de)	1981-01-07	Verfahren zur herstellung von estern aus methyl-1 piperidinol-4
DE69023045T2 (de)	1996-04-11	Carboxamidderivate.
DE2748291B2 (de)	1979-03-01	Substituierte 13-Benzodioxan-4one und Verfahren zu ihrer Herstellung sowie Verwendung dieser Verbindungen bei der Bekämpfung von Entzündungen
DE2609746A1 (de)	1976-10-14	Piperazinverbindungen sowie arzneimittel, die diese verbindungen enthalten
DE2517020A1 (de)	1975-11-06	Alkanolaminderivate, verfahren zu ihrer herstellung und diese verbindungen enthaltende arzneimittel
DE2004301A1 (de)	1970-09-03	Phenylserinderivate
DE2462460C3 (de)	1980-02-14	In 8-Stellung des Chinolinrings substituierte 2-(4-Chinolylamino)-benzoesäure-2-(4-phenylpiperazino)-äthylester, Verfahren zu deren Herstellung und Arzneimittel, welche diese enthalten
DE2641129A1 (de)	1977-03-24	Derivate des 5-aminomethylthiazols, ihr herstellungsverfahren und pharmazeutische zusammensetzungen
EP0498011B1 (fr)	1995-04-26	Sels de l'acide 2-(2,6-dichloroanilino)-phénylacétique procédé pour leur préparation et leur application comme préparation pharmaceutique pour utilisation topique
CH643831A5 (de)	1984-06-29	Cinnamyl-moranolin-derivate.
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AT230372B (de)	1963-12-10	Verfahren zur Herstellung von neuen 4-Amino-1-phenyl-2,3-dimethyl-pyrazolon-Derivaten
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