DD251976A5 - Verfahren zur isolierung von (+)-6-chlor-5,10-dihydro-5-((l-methyl-4-piperidinyl)-acetyl)-11h-dibenzo(b,2)(1,4)-diazepin-11-on - Google Patents

Verfahren zur isolierung von (+)-6-chlor-5,10-dihydro-5-((l-methyl-4-piperidinyl)-acetyl)-11h-dibenzo(b,2)(1,4)-diazepin-11-on Download PDF

Info

Publication number: DD251976A5
Authority: DD; German Democratic Republic
Prior art keywords: dihydro; methyl; chloro; piperidinyl; dibenzo
Prior art date: 1985-09-05

Application number

DD86294151A

Other languages

German (de)

English (en)

Inventor

Trummlitz

Engel

Eberlein

Mihm

Giachetti

Original Assignee

��K@��@��@��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.)

1985-09-05

Filing date

1986-09-04

Publication date

1987-12-02

1986-09-04 Application filed by ��K@��@��@��k�� filed Critical ��K@��@��@��k��

1987-12-02 Publication of DD251976A5 publication Critical patent/DD251976A5/de

Links

238000000034 method Methods 0.000 title claims abstract description 12
238000002955 isolation Methods 0.000 title claims abstract description 5
150000003839 salts Chemical class 0.000 claims abstract description 12
239000000203 mixture Substances 0.000 claims abstract description 10
239000002253 acid Substances 0.000 claims abstract description 7
239000002904 solvent Substances 0.000 claims abstract description 6
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 abstract description 5
150000001875 compounds Chemical class 0.000 claims abstract description 5
150000007524 organic acids Chemical class 0.000 claims abstract description 5
235000005985 organic acids Nutrition 0.000 claims abstract description 5
150000007522 mineralic acids Chemical class 0.000 claims abstract description 4
239000003513 alkali Substances 0.000 claims abstract description 3
239000012458 free base Substances 0.000 claims abstract 4
239000003814 drug Substances 0.000 claims abstract 3
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 22
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 14
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 8
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
AUONNNVJUCSETH-UHFFFAOYSA-N icosanoyl icosanoate Chemical compound CCCCCCCCCCCCCCCCCCCC(=O)OC(=O)CCCCCCCCCCCCCCCCCCC AUONNNVJUCSETH-UHFFFAOYSA-N 0.000 claims description 4
238000002360 preparation method Methods 0.000 claims description 4
229940079593 drug Drugs 0.000 claims 1
125000003386 piperidinyl group Chemical group 0.000 claims 1
-1 (1-methyl-4-piperidinyl) acetyl Chemical group 0.000 abstract description 6
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
239000000829 suppository Substances 0.000 description 7
235000002906 tartaric acid Nutrition 0.000 description 7
239000011975 tartaric acid Substances 0.000 description 7
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 6
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 6
238000002844 melting Methods 0.000 description 6
230000008018 melting Effects 0.000 description 6
239000000243 solution Substances 0.000 description 6
239000000460 chlorine Substances 0.000 description 5
230000000694 effects Effects 0.000 description 5
UFJWXHOFKIGIAF-UHFFFAOYSA-N 1-chloro-11-[2-(1-methylpiperidin-4-yl)acetyl]-5h-benzo[b][1,4]benzodiazepin-6-one Chemical compound C1CN(C)CCC1CC(=O)N1C2=C(Cl)C=CC=C2NC(=O)C2=CC=CC=C21 UFJWXHOFKIGIAF-UHFFFAOYSA-N 0.000 description 4
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Chemical compound 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 4
241000700159 Rattus Species 0.000 description 4
239000004480 active ingredient Substances 0.000 description 4
239000013543 active substance Substances 0.000 description 4
238000000354 decomposition reaction Methods 0.000 description 4
239000008298 dragée Substances 0.000 description 4
HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 4
238000004519 manufacturing process Methods 0.000 description 4
230000003287 optical effect Effects 0.000 description 4
210000001187 pylorus Anatomy 0.000 description 4
239000000126 substance Substances 0.000 description 4
229940095064 tartrate Drugs 0.000 description 4
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
241001465754 Metazoa Species 0.000 description 3
150000007513 acids Chemical class 0.000 description 3
230000037396 body weight Effects 0.000 description 3
238000006243 chemical reaction Methods 0.000 description 3
KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
238000002474 experimental method Methods 0.000 description 3
239000012452 mother liquor Substances 0.000 description 3
229920001592 potato starch Polymers 0.000 description 3
238000000926 separation method Methods 0.000 description 3
239000011780 sodium chloride Substances 0.000 description 3
NOOLISFMXDJSKH-UTLUCORTSA-N (+)-Neomenthol Chemical compound CC(C)[C@@H]1CC[C@@H](C)C[C@@H]1O NOOLISFMXDJSKH-UTLUCORTSA-N 0.000 description 2
UDIPTWFVPPPURJ-UHFFFAOYSA-M Cyclamate Chemical compound [Na+].[O-]S(=O)(=O)NC1CCCCC1 UDIPTWFVPPPURJ-UHFFFAOYSA-M 0.000 description 2
NOOLISFMXDJSKH-UHFFFAOYSA-N DL-menthol Natural products CC(C)C1CCC(C)CC1O NOOLISFMXDJSKH-UHFFFAOYSA-N 0.000 description 2
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 2
VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-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
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 description 2
RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 2
239000008346 aqueous phase Substances 0.000 description 2
239000002585 base Substances 0.000 description 2
238000001816 cooling Methods 0.000 description 2
239000000625 cyclamic acid and its Na and Ca salt Substances 0.000 description 2
230000002496 gastric effect Effects 0.000 description 2
210000004051 gastric juice Anatomy 0.000 description 2
235000019359 magnesium stearate Nutrition 0.000 description 2
229940041616 menthol Drugs 0.000 description 2
LXCFILQKKLGQFO-UHFFFAOYSA-N methylparaben Chemical compound COC(=O)C1=CC=C(O)C=C1 LXCFILQKKLGQFO-UHFFFAOYSA-N 0.000 description 2
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 2
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
239000000047 product Substances 0.000 description 2
230000006340 racemization Effects 0.000 description 2
238000001953 recrystallisation Methods 0.000 description 2
229960001462 sodium cyclamate Drugs 0.000 description 2
238000003756 stirring Methods 0.000 description 2
KUPPZIQYLWKDKQ-UHFFFAOYSA-N 1-(1-chloro-5,6-dihydrobenzo[b][1,4]benzodiazepin-11-yl)-2-(1-methylpiperidin-4-yl)ethanone Chemical compound ClC1=CC=CC=2NCC3=C(N(C=21)C(CC1CCN(CC1)C)=O)C=CC=C3 KUPPZIQYLWKDKQ-UHFFFAOYSA-N 0.000 description 1
GBJFSZCDZHSAOP-UHFFFAOYSA-N 2,3-dihydroxy-4-methoxy-4-oxobutanoic acid Chemical compound COC(=O)C(O)C(O)C(O)=O GBJFSZCDZHSAOP-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
229940090248 4-hydroxybenzoic acid Drugs 0.000 description 1
FKYRATZIFPBPGO-UHFFFAOYSA-N 7,8-dihydrobenzo[b][1,4]benzodiazepin-6-one Chemical compound O=C1N=C2C=CC=CC2=NC2=C1CCC=C2 FKYRATZIFPBPGO-UHFFFAOYSA-N 0.000 description 1
206010002091 Anaesthesia Diseases 0.000 description 1
FEWJPZIEWOKRBE-LWMBPPNESA-L D-tartrate(2-) Chemical compound [O-]C(=O)[C@@H](O)[C@H](O)C([O-])=O FEWJPZIEWOKRBE-LWMBPPNESA-L 0.000 description 1
241000700157 Rattus norvegicus Species 0.000 description 1
244000269722 Thea sinensis Species 0.000 description 1
238000002441 X-ray diffraction Methods 0.000 description 1
210000000683 abdominal cavity Anatomy 0.000 description 1
230000009858 acid secretion Effects 0.000 description 1
239000003708 ampul Substances 0.000 description 1
230000037005 anaesthesia Effects 0.000 description 1
238000004458 analytical method Methods 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
235000013871 bee wax Nutrition 0.000 description 1
239000012166 beeswax Substances 0.000 description 1
230000009286 beneficial effect Effects 0.000 description 1
LSPHULWDVZXLIL-QUBYGPBYSA-N camphoric acid Chemical compound CC1(C)[C@H](C(O)=O)CC[C@]1(C)C(O)=O LSPHULWDVZXLIL-QUBYGPBYSA-N 0.000 description 1
239000002775 capsule Substances 0.000 description 1
238000004296 chiral HPLC Methods 0.000 description 1
229910052801 chlorine Inorganic materials 0.000 description 1
125000001309 chloro group Chemical group Cl* 0.000 description 1
210000001072 colon Anatomy 0.000 description 1
239000013078 crystal Substances 0.000 description 1
238000002425 crystallisation Methods 0.000 description 1
230000008025 crystallization Effects 0.000 description 1
201000010099 disease Diseases 0.000 description 1
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
238000011156 evaluation Methods 0.000 description 1
239000000284 extract Substances 0.000 description 1
239000001530 fumaric acid Substances 0.000 description 1
210000001035 gastrointestinal tract Anatomy 0.000 description 1
239000008187 granular material Substances 0.000 description 1
238000003306 harvesting Methods 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
238000004128 high performance liquid chromatography Methods 0.000 description 1
WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
238000001990 intravenous administration Methods 0.000 description 1
239000002085 irritant Substances 0.000 description 1
231100000021 irritant Toxicity 0.000 description 1
238000012417 linear regression Methods 0.000 description 1
239000007788 liquid Substances 0.000 description 1
229910052943 magnesium sulfate Inorganic materials 0.000 description 1
235000019341 magnesium sulphate Nutrition 0.000 description 1
UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 1
229960002216 methylparaben Drugs 0.000 description 1
210000003097 mucus Anatomy 0.000 description 1
229910052757 nitrogen Inorganic materials 0.000 description 1
125000004433 nitrogen atom Chemical group N* 0.000 description 1
239000012074 organic phase Substances 0.000 description 1
FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 1
239000002245 particle Substances 0.000 description 1
239000008194 pharmaceutical composition Substances 0.000 description 1
239000000825 pharmaceutical preparation Substances 0.000 description 1
239000012071 phase Substances 0.000 description 1
229910000027 potassium carbonate Inorganic materials 0.000 description 1
230000003389 potentiating effect Effects 0.000 description 1
239000004405 propyl p-hydroxybenzoate Substances 0.000 description 1
235000010232 propyl p-hydroxybenzoate Nutrition 0.000 description 1
QELSKZZBTMNZEB-UHFFFAOYSA-N propylparaben Chemical compound CCCOC(=O)C1=CC=C(O)C=C1 QELSKZZBTMNZEB-UHFFFAOYSA-N 0.000 description 1
230000001681 protective effect Effects 0.000 description 1
239000000377 silicon dioxide Substances 0.000 description 1
VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
239000007787 solid Substances 0.000 description 1
238000001228 spectrum Methods 0.000 description 1
230000001954 sterilising effect Effects 0.000 description 1
238000004659 sterilization and disinfection Methods 0.000 description 1
210000002784 stomach Anatomy 0.000 description 1
239000006228 supernatant Substances 0.000 description 1
239000003826 tablet Substances 0.000 description 1
239000000454 talc Substances 0.000 description 1
229910052623 talc Inorganic materials 0.000 description 1
238000004448 titration 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
238000012982 x-ray structure analysis Methods 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
- C07D401/06—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 carbon chain containing only aliphatic carbon atoms
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system

Landscapes

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

DD86294151A 1985-09-05 1986-09-04 Verfahren zur isolierung von (+)-6-chlor-5,10-dihydro-5-((l-methyl-4-piperidinyl)-acetyl)-11h-dibenzo(b,2)(1,4)-diazepin-11-on DD251976A5 (de)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
DE19853531682 DE3531682A1 (de)	1985-09-05	1985-09-05	(+)-6-chlor-5,10-dihydro-5-((1-methyl-4- piperidinyl)acetyl)-11h-dibenzo(b,e)(1,4) diazepin-11-on, seine isolierung und verwendung als arzneimittel

Publications (1)

Publication Number	Publication Date
DD251976A5 true DD251976A5 (de)	1987-12-02

Family

ID=6280185

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
DD86294151A DD251976A5 (de)	1985-09-05	1986-09-04	Verfahren zur isolierung von (+)-6-chlor-5,10-dihydro-5-((l-methyl-4-piperidinyl)-acetyl)-11h-dibenzo(b,2)(1,4)-diazepin-11-on

Country Status (17)

Country	Link
US (1)	US4668674A (fr)
EP (1)	EP0214528A3 (fr)
JP (1)	JPS6256478A (fr)
KR (1)	KR870003097A (fr)
AU (1)	AU582271B2 (fr)
DD (1)	DD251976A5 (fr)
DE (1)	DE3531682A1 (fr)
DK (1)	DK423886A (fr)
ES (1)	ES2001290A6 (fr)
FI (1)	FI863549A7 (fr)
GR (1)	GR862242B (fr)
HU (1)	HU195499B (fr)
IL (1)	IL79933A0 (fr)
NO (1)	NO863539L (fr)
NZ (1)	NZ217462A (fr)
PT (1)	PT83308B (fr)
ZA (1)	ZA866703B (fr)

Families Citing this family (7)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
GB2206880B (en) *	1987-07-16	1991-04-24	Farmos Oy	Optical isomers of an imidazole derivative
DE3738980A1 (de) *	1987-11-17	1989-05-24	Thomae Gmbh Dr K	Mittel zur behandlung von ischaemischen herzerkrankungen
EP0330756B1 (fr) *	1987-12-22	1996-03-27	Byk Gulden Lomberg Chemische Fabrik GmbH	Composés thiénotricycliques pour le traitement des maladies bronchiques
DE4138909A1 (de) *	1991-11-27	1993-06-03	Bayer Ag	Aminoalkyl-substituierte 5,6-dihydro-dibenz(b,e)azepin-6,11-dion-11-oxime
US5439109A (en) *	1993-12-28	1995-08-08	Bag-It Products Corp.	Line storage device
US6333322B1 (en) *	1996-03-13	2001-12-25	Eisai Co., Ltd.	Nitrogen-containing tricyclic compounds and drugs containing the same
EP4587029A1 (fr) *	2022-09-12	2025-07-23	Invea Therapeutics, Inc.	Compositions et procédés de traitement de maladies inflammatoires

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE3028001A1 (de) *	1980-07-24	1982-02-18	Dr. Karl Thomae Gmbh, 7950 Biberach	Neue, in 5-stellung substituierte 5,10-dihydro-11h-dibenzo (b,e)(1,4) diazepin-11-one, verfahren zu ihrer herstellung und diese verbindung enthaltende arzneimittel
DE3204157A1 (de) *	1982-02-06	1983-08-11	Dr. Karl Thomae Gmbh, 7950 Biberach	Substituierte dibenzodiazepinone, verfahren zu ihrer herstellung und sie enthaltende arzneimittel
DE3402060A1 (de) *	1984-01-21	1985-08-01	Dr. Karl Thomae Gmbh, 7950 Biberach	Substituierte 5,11-dihydro-6h-dibenz(b,e)azepin-6-one, verfahren zu ihrer herstellung und diese verbindungen enthaltende arzneimittel
DE3409237A1 (de) *	1984-03-14	1985-09-19	Dr. Karl Thomae Gmbh, 7950 Biberach	Kondensierte diazepinone, verfahren zu ihrer herstellung und diese verbindungen enthaltende arzneimittel

1985
- 1985-09-05 DE DE19853531682 patent/DE3531682A1/de not_active Withdrawn
1986
- 1986-08-19 US US06/898,153 patent/US4668674A/en not_active Expired - Fee Related
- 1986-08-21 EP EP86111580A patent/EP0214528A3/fr not_active Withdrawn
- 1986-09-01 GR GR862242A patent/GR862242B/el unknown
- 1986-09-03 IL IL79933A patent/IL79933A0/xx unknown
- 1986-09-03 FI FI863549A patent/FI863549A7/fi not_active IP Right Cessation
- 1986-09-04 NZ NZ217462A patent/NZ217462A/xx unknown
- 1986-09-04 PT PT83308A patent/PT83308B/pt unknown
- 1986-09-04 ZA ZA866703A patent/ZA866703B/xx unknown
- 1986-09-04 KR KR1019860007408A patent/KR870003097A/ko not_active Withdrawn
- 1986-09-04 AU AU62341/86A patent/AU582271B2/en not_active Ceased
- 1986-09-04 DK DK423886A patent/DK423886A/da not_active Application Discontinuation
- 1986-09-04 NO NO863539A patent/NO863539L/no unknown
- 1986-09-04 DD DD86294151A patent/DD251976A5/de unknown
- 1986-09-04 HU HU863826A patent/HU195499B/hu unknown
- 1986-09-04 ES ES8601622A patent/ES2001290A6/es not_active Expired
- 1986-09-04 JP JP61208831A patent/JPS6256478A/ja active Pending

Also Published As

Publication number	Publication date
GR862242B (en)	1987-01-02
US4668674A (en)	1987-05-26
AU6234186A (en)	1987-03-12
EP0214528A2 (fr)	1987-03-18
FI863549A7 (fi)	1987-09-06
PT83308A (de)	1986-10-01
FI863549A0 (fi)	1986-09-03
NZ217462A (en)	1988-11-29
PT83308B (de)	1988-10-07
JPS6256478A (ja)	1987-03-12
DK423886D0 (da)	1986-09-04
HU195499B (en)	1988-05-30
FI863549L (fi)	1987-03-06
KR870003097A (ko)	1987-04-15
IL79933A0 (en)	1986-12-31
EP0214528A3 (fr)	1987-08-05
NO863539D0 (no)	1986-09-04
ZA866703B (en)	1988-05-25
HUT42472A (en)	1987-07-28
AU582271B2 (en)	1989-03-16
NO863539L (no)	1987-03-06
DK423886A (da)	1987-03-06
DE3531682A1 (de)	1987-03-12
ES2001290A6 (es)	1988-05-01

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DE3700172A1 (de)	1987-07-09	Wasserloesliche n-(methyl)-glucamin- und glucaminsalze, verfahren zu ihrer herstellung und diese enthaltende arzneimittel
DE69033369T2 (de)	2000-05-11	1,2,3,4-Tetrahydro-9-Akridinamine-Derivate
DE3873578T2 (de)	1993-03-04	Verwendung von tetrahydrobenz(c,d)indol-6-carboxamiden zur herstellung von arzneimitteln zur behandlung von angstzustaenden.
DE3744947C2 (fr)	1992-07-16
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