DD143777A5 - Verfahren zur herstellung von 6-cyclopropyl-1,3-dihydro-5-phenyl-2-oxo-2h-thieno-eckige klammer auf 2,3-e eckige klammer zu-diazepin - Google Patents

Verfahren zur herstellung von 6-cyclopropyl-1,3-dihydro-5-phenyl-2-oxo-2h-thieno-eckige klammer auf 2,3-e eckige klammer zu-diazepin Download PDF

Info

Publication number: DD143777A5
Authority: DD; German Democratic Republic
Prior art keywords: cyclopropyl; thieno; benzoyl; dihydro; oxo
Prior art date: 1977-03-31

Application number

DD78213659A

Other languages

German (de)

English (en)

Inventor

Jean C Cognaco

Original Assignee

Hexachimie

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.)

1977-03-31

Filing date

1978-03-29

Publication date

1980-09-10

1978-03-29 Application filed by Hexachimie filed Critical Hexachimie

1980-09-10 Publication of DD143777A5 publication Critical patent/DD143777A5/de

Links

238000000034 method Methods 0.000 title claims abstract description 9
LRANPJDWHYRCER-UHFFFAOYSA-N 1,2-diazepine Chemical compound N1C=CC=CC=N1 LRANPJDWHYRCER-UHFFFAOYSA-N 0.000 title description 3
238000002360 preparation method Methods 0.000 claims abstract description 11
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 34
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 18
150000001875 compounds Chemical class 0.000 claims description 16
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 15
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 12
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 10
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 9
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 8
229910021529 ammonia Inorganic materials 0.000 claims description 5
238000006243 chemical reaction Methods 0.000 claims description 5
NKKMVIVFRUYPLQ-NSCUHMNNSA-N crotononitrile Chemical compound C\C=C\C#N NKKMVIVFRUYPLQ-NSCUHMNNSA-N 0.000 claims description 5
238000010992 reflux Methods 0.000 claims description 5
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 4
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 4
HVCFCNAITDHQFX-UHFFFAOYSA-N 1-cyclopropylethanone Chemical compound CC(=O)C1CC1 HVCFCNAITDHQFX-UHFFFAOYSA-N 0.000 claims description 3
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 3
PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 claims description 3
ZJRCIQAMTAINCB-UHFFFAOYSA-N benzoylacetonitrile Chemical compound N#CCC(=O)C1=CC=CC=C1 ZJRCIQAMTAINCB-UHFFFAOYSA-N 0.000 claims description 3
239000011593 sulfur Substances 0.000 claims description 3
229910052717 sulfur Inorganic materials 0.000 claims description 3
LSTRKXWIZZZYAS-UHFFFAOYSA-N 2-bromoacetyl bromide Chemical compound BrCC(Br)=O LSTRKXWIZZZYAS-UHFFFAOYSA-N 0.000 claims description 2
MDWWPRNUHKMQCT-UHFFFAOYSA-N 2-cyclopropylthiophene Chemical compound C1CC1C1=CC=CS1 MDWWPRNUHKMQCT-UHFFFAOYSA-N 0.000 claims description 2
ZVQOOHYFBIDMTQ-UHFFFAOYSA-N [methyl(oxido){1-[6-(trifluoromethyl)pyridin-3-yl]ethyl}-lambda(6)-sulfanylidene]cyanamide Chemical compound N#CN=S(C)(=O)C(C)C1=CC=C(C(F)(F)F)N=C1 ZVQOOHYFBIDMTQ-UHFFFAOYSA-N 0.000 claims description 2
238000005576 amination reaction Methods 0.000 claims description 2
230000015572 biosynthetic process Effects 0.000 claims description 2
238000004587 chromatography analysis Methods 0.000 claims description 2
238000010828 elution Methods 0.000 claims description 2
238000010438 heat treatment Methods 0.000 claims description 2
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
238000007363 ring formation reaction Methods 0.000 claims description 2
238000003786 synthesis reaction Methods 0.000 claims description 2
125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims 1
238000000926 separation method Methods 0.000 claims 1
208000025865 Ulcer Diseases 0.000 description 11
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 10
238000003756 stirring Methods 0.000 description 10
239000000203 mixture Substances 0.000 description 9
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 8
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 8
231100000397 ulcer Toxicity 0.000 description 8
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 7
230000001681 protective effect Effects 0.000 description 7
210000001035 gastrointestinal tract Anatomy 0.000 description 6
241000700159 Rattus Species 0.000 description 5
229910052943 magnesium sulfate Inorganic materials 0.000 description 5
235000019341 magnesium sulphate Nutrition 0.000 description 5
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
230000028327 secretion Effects 0.000 description 4
210000002784 stomach Anatomy 0.000 description 4
HEKWHKRUDIKHND-UHFFFAOYSA-N (2-amino-4-cyclopropylthiophen-3-yl)-phenylmethanone Chemical compound C=1C=CC=CC=1C(=O)C1=C(N)SC=C1C1CC1 HEKWHKRUDIKHND-UHFFFAOYSA-N 0.000 description 3
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
238000001035 drying Methods 0.000 description 3
230000036269 ulceration Effects 0.000 description 3
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 2
UCMIRNVEIXFBKS-UHFFFAOYSA-N beta-alanine Chemical compound NCCC(O)=O UCMIRNVEIXFBKS-UHFFFAOYSA-N 0.000 description 2
239000003814 drug Substances 0.000 description 2
230000000694 effects Effects 0.000 description 2
238000001704 evaporation Methods 0.000 description 2
230000008020 evaporation Effects 0.000 description 2
239000003921 oil Substances 0.000 description 2
235000019198 oils Nutrition 0.000 description 2
239000003208 petroleum Substances 0.000 description 2
230000000144 pharmacologic effect Effects 0.000 description 2
238000000746 purification Methods 0.000 description 2
239000000126 substance Substances 0.000 description 2
230000001225 therapeutic effect Effects 0.000 description 2
238000005406 washing Methods 0.000 description 2
XVMSFILGAMDHEY-UHFFFAOYSA-N 6-(4-aminophenyl)sulfonylpyridin-3-amine Chemical compound C1=CC(N)=CC=C1S(=O)(=O)C1=CC=C(N)C=N1 XVMSFILGAMDHEY-UHFFFAOYSA-N 0.000 description 1
206010002091 Anaesthesia Diseases 0.000 description 1
108091003079 Bovine Serum Albumin Proteins 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
OUYCCCASQSFEME-QMMMGPOBSA-N L-tyrosine Chemical compound OC(=O)[C@@H](N)CC1=CC=C(O)C=C1 OUYCCCASQSFEME-QMMMGPOBSA-N 0.000 description 1
102000057297 Pepsin A Human genes 0.000 description 1
108090000284 Pepsin A Proteins 0.000 description 1
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
230000007059 acute toxicity Effects 0.000 description 1
231100000403 acute toxicity Toxicity 0.000 description 1
230000037005 anaesthesia Effects 0.000 description 1
229940000635 beta-alanine Drugs 0.000 description 1
210000004204 blood vessel Anatomy 0.000 description 1
230000037396 body weight Effects 0.000 description 1
125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
235000005911 diet Nutrition 0.000 description 1
230000037213 diet Effects 0.000 description 1
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
208000035475 disorder Diseases 0.000 description 1
239000002552 dosage form Substances 0.000 description 1
238000011156 evaluation Methods 0.000 description 1
238000001914 filtration Methods 0.000 description 1
235000013305 food Nutrition 0.000 description 1
210000004051 gastric juice Anatomy 0.000 description 1
239000007903 gelatin capsule Substances 0.000 description 1
239000008103 glucose Substances 0.000 description 1
230000007062 hydrolysis Effects 0.000 description 1
238000006460 hydrolysis reaction Methods 0.000 description 1
230000008595 infiltration Effects 0.000 description 1
238000001764 infiltration Methods 0.000 description 1
INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
231100000636 lethal dose Toxicity 0.000 description 1
238000005259 measurement Methods 0.000 description 1
125000000896 monocarboxylic acid group Chemical group 0.000 description 1
125000002560 nitrile group Chemical group 0.000 description 1
QYSGYZVSCZSLHT-UHFFFAOYSA-N octafluoropropane Chemical compound FC(F)(F)C(F)(F)C(F)(F)F QYSGYZVSCZSLHT-UHFFFAOYSA-N 0.000 description 1
239000012074 organic phase Substances 0.000 description 1
229940111202 pepsin Drugs 0.000 description 1
230000001175 peptic effect Effects 0.000 description 1
210000004767 rumen Anatomy 0.000 description 1
239000011780 sodium chloride Substances 0.000 description 1
229910000104 sodium hydride Inorganic materials 0.000 description 1
239000012312 sodium hydride Substances 0.000 description 1
239000007787 solid Substances 0.000 description 1
239000002904 solvent Substances 0.000 description 1
231100001274 therapeutic index Toxicity 0.000 description 1
229930192474 thiophene Natural products 0.000 description 1
231100000419 toxicity Toxicity 0.000 description 1
230000001988 toxicity Effects 0.000 description 1
OUYCCCASQSFEME-UHFFFAOYSA-N tyrosine Natural products OC(=O)C(N)CC1=CC=C(O)C=C1 OUYCCCASQSFEME-UHFFFAOYSA-N 0.000 description 1
235000015112 vegetable and seed oil Nutrition 0.000 description 1
239000008158 vegetable oil Substances 0.000 description 1
238000005303 weighing Methods 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
- C07D495/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D495/04—Ortho-condensed systems
- 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
- A61P1/04—Drugs for disorders of the alimentary tract or the digestive system for ulcers, gastritis or reflux esophagitis, e.g. antacids, inhibitors of acid secretion, mucosal protectants
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
- C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
- C07D333/26—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom 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
- C07D333/30—Hetero atoms other than halogen
- C07D333/36—Nitrogen atoms

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)
Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

DD78213659A 1977-03-31 1978-03-29 Verfahren zur herstellung von 6-cyclopropyl-1,3-dihydro-5-phenyl-2-oxo-2h-thieno-eckige klammer auf 2,3-e eckige klammer zu-diazepin DD143777A5 (de)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
GB1358777		1977-03-31

Publications (1)

Publication Number	Publication Date
DD143777A5 true DD143777A5 (de)	1980-09-10

Family

ID=10025687

Family Applications (2)

Application Number	Title	Priority Date	Filing Date
DD78213659A DD143777A5 (de)	1977-03-31	1978-03-29	Verfahren zur herstellung von 6-cyclopropyl-1,3-dihydro-5-phenyl-2-oxo-2h-thieno-eckige klammer auf 2,3-e eckige klammer zu-diazepin
DD78204460A DD137108A5 (de)	1977-03-31	1978-03-29	Verfahren zur herstellung von 6-cyclopropyl-1.3-dihydro-1-methyl-5-phenyl-2-oxo-2h-thieno-eckige klammer auf 2.3-e eckige klammer zu-diazepin und seiner salze

Family Applications After (1)

Application Number	Title	Priority Date	Filing Date
DD78204460A DD137108A5 (de)	1977-03-31	1978-03-29	Verfahren zur herstellung von 6-cyclopropyl-1.3-dihydro-1-methyl-5-phenyl-2-oxo-2h-thieno-eckige klammer auf 2.3-e eckige klammer zu-diazepin und seiner salze

Country Status (17)

Country	Link
US (1)	US4156009A (da)
JP (1)	JPS53121791A (da)
AR (1)	AR215171A1 (da)
AU (1)	AU3495678A (da)
BE (1)	BE865278A (da)
DD (2)	DD143777A5 (da)
DE (1)	DE2813996A1 (da)
DK (1)	DK135478A (da)
ES (2)	ES468382A1 (da)
FR (1)	FR2385721A1 (da)
GR (1)	GR62853B (da)
NL (1)	NL7803431A (da)
NO (1)	NO781102L (da)
PT (1)	PT67813A (da)
SE (1)	SE7803604L (da)
SU (1)	SU715027A3 (da)
ZA (1)	ZA781694B (da)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
GB0225554D0 (en) *	2002-11-01	2002-12-11	Syngenta Participations Ag	Chemical compounds
WO2025212920A1 (en)	2024-04-03	2025-10-09	Children's Hospital Medical Center	Multi-zonal liver organoids

Family Cites Families (8)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
GB1256548A (da) *	1968-12-10	1971-12-08
CA927388A (en) *	1970-02-17	1973-05-29	Nakanishi Michio	Thieno (2,3-e)(1,4)diazepin-2-ones
US3806512A (en) *	1970-09-03	1974-04-23	Yoshitomi Pharmaceutical	2-amino-3-pyridylcarbonylthiophene compounds
FI53214C (da) *	1970-11-16	1978-03-10	Sumitomo Chemical Co
US3872089A (en) *	1971-05-14	1975-03-18	Hoffmann La Roche	Substituted thienodiazepines
GB1345998A (en) *	1971-05-31	1974-02-06	Yoshitomi Pharmaceutical	Thienodiazepine compounds and pharmaceutical compositions containining them
JPS5750794B2 (da) *	1973-02-03	1982-10-28
JPS5729472B2 (da) *	1974-05-02	1982-06-23

1978
- 1978-03-16 FR FR7807697A patent/FR2385721A1/fr not_active Withdrawn
- 1978-03-23 GR GR55787A patent/GR62853B/el unknown
- 1978-03-23 ZA ZA00781694A patent/ZA781694B/xx unknown
- 1978-03-23 PT PT67813A patent/PT67813A/pt unknown
- 1978-03-24 BE BE2056799A patent/BE865278A/xx unknown
- 1978-03-27 JP JP3525278A patent/JPS53121791A/ja active Pending
- 1978-03-27 US US05/890,410 patent/US4156009A/en not_active Expired - Lifetime
- 1978-03-27 AR AR271535A patent/AR215171A1/es active
- 1978-03-28 DK DK135478A patent/DK135478A/da unknown
- 1978-03-29 DD DD78213659A patent/DD143777A5/de unknown
- 1978-03-29 DD DD78204460A patent/DD137108A5/xx unknown
- 1978-03-30 ES ES468382A patent/ES468382A1/es not_active Expired
- 1978-03-30 NO NO781102A patent/NO781102L/no unknown
- 1978-03-30 SE SE7803604A patent/SE7803604L/xx unknown
- 1978-03-30 SU SU782594351A patent/SU715027A3/ru active
- 1978-03-31 DE DE19782813996 patent/DE2813996A1/de active Pending
- 1978-03-31 NL NL7803431A patent/NL7803431A/xx not_active Application Discontinuation
- 1978-04-11 AU AU34956/78A patent/AU3495678A/en active Pending
1979
- 1979-01-25 ES ES477164A patent/ES477164A1/es not_active Expired

Also Published As

Publication number	Publication date
SE7803604L (sv)	1978-10-01
DE2813996A1 (de)	1978-10-05
ES477164A1 (es)	1979-10-16
US4156009A (en)	1979-05-22
ES468382A1 (es)	1979-10-01
SU715027A3 (ru)	1980-02-05
FR2385721A1 (fr)	1978-10-27
DD137108A5 (de)	1979-08-15
NL7803431A (nl)	1978-10-03
GR62853B (en)	1979-06-20
AR215171A1 (es)	1979-09-14
JPS53121791A (en)	1978-10-24
BE865278A (fr)	1978-09-25
NO781102L (no)	1978-10-03
ZA781694B (en)	1979-03-28
PT67813A (fr)	1978-04-01
AU3495678A (en)	1979-10-18
DK135478A (da)	1978-10-01

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EP0008391A1 (de)	1980-03-05	Benzimidazole, deren Herstellung und diese Verbindungen enthaltende Arzneimittel
EP0528922A1 (de)	1993-03-03	Neue sulfonylverbindungen
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DE2302866A1 (de)	1973-08-02	Neue 1-substituierte-1,4-dihydropyridinderivate
DE2802864A1 (de)	1978-07-27	3-isobutoxy-2-pyrrolidino-n-phenyl- n-benzylpropylamin, verfahren zu seiner herstellung und es enthaltende arzneimittel
DE2517020C3 (de)	1978-03-16	N- [l-(3-Trifluormethyl-phenyl)-prop-2-yl] -glycinester, Verfahren zu ihrer' Herstellung und diese Ester enthaltende Arzneimittel
DE2156499A1 (de)	1972-05-18	N-substituierte 2-Carboxy-l-azacyclische Verbindungen
DE2229845B2 (de)	1980-01-10	6-o-Halogenphenyl-4H-s-triazolo [3,4-c] thieno [2,3e] [1,4] diazepine, Verfahren zu deren Herstellung und diese enthaltende pharmazeutische Massen
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DE2144568A1 (de)	1972-03-30	Neue Derivate der Phenyl-5-pyrazolcarbonsäuren-3, Verfahren zu ihrer Herstellung und ihre Verwendung
DE2314985A1 (de)	1974-10-17	1-(imidazol-1-yl)-isochinoline und verfahren zu ihrer herstellung
EP0209022B1 (de)	1989-10-18	4-Substituierte 10-Cyanmethylen-thieno[4,3-e]-benzo-azepine
DE3134945A1 (de)	1983-03-17	Substituierte 2-amino-3,4-dihydropyridinderivate, verfahren zu ihrer herstellung und ihre verwendung in arzneimittel
DE2813996A1 (de)	1978-10-05	6-cyclopropyl-1.3-dihydro-1-methyl- 5-phenyl-2-oxo-2h-thieno-eckige klammer auf 2.3-e eckige klammer zu-diazepin, seine herstellung und pharmazeutische mittel
EP0000479B1 (de)	1981-01-07	Substituierte 1-Piperazinyl-4H-s-triazolo (3,4-c)thieno(2,3-e)1,4-diazepine, Verfahren zu deren Herstellung und diese enthaltende Arzneimittel
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DE2632951A1 (de)	1977-02-10	Neue 1-deoxy-2,3-0-alkyliden-ribofuranuronsaeurederivate, verfahren zu ihrer herstellung und sie enthaltende arzneimittel
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DE3310796A1 (de)	1983-09-29	Substituierte ethenylderivate von 1h-pyrazolo-(1,5-a)-pyrimidin, verfahren zur herstellung derselben, sowie diese enthaltende pharmazeutische praeparate
DE1957783A1 (de)	1971-05-19	Neue substituierte Arylhydrazino-pyrroline,-tetrahydro-pyridine und -tetrahydro-7H-azepine sowie Verfahren zu deren Herstellung
DE2158468A1 (de)	1972-07-13	Neue Imidazolin-Verbindungen, Verfahren zu ihrer Herstellung und diese enthaltende pharmazeutische Präparate
DE10042093A1 (de)	2002-03-07	Antikonvulsiv wirkende 6,7-Dihydro-pyrrolo[3,4-d]pyridin-5-one und Verfahren zu deren Darstellung
AT368494B (de)	1982-10-11	Verfahren zur herstellung von neuen nitrosubstituierten 1,4-dihydropyridinen