DE2653251A1 - Azabicyclo eckige klammer auf 3.1.o eckige klammer zu hexan-derivate, ihre herstellung und verwendung - Google Patents
Azabicyclo eckige klammer auf 3.1.o eckige klammer zu hexan-derivate, ihre herstellung und verwendungInfo
- Publication number
- DE2653251A1 DE2653251A1 DE19762653251 DE2653251A DE2653251A1 DE 2653251 A1 DE2653251 A1 DE 2653251A1 DE 19762653251 DE19762653251 DE 19762653251 DE 2653251 A DE2653251 A DE 2653251A DE 2653251 A1 DE2653251 A1 DE 2653251A1
- Authority
- DE
- Germany
- Prior art keywords
- carbon atoms
- formula
- azabicyclo
- salts
- hexane
- Prior art date
- Legal status (The legal status 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 status listed.)
- Withdrawn
Links
- 238000004519 manufacturing process Methods 0.000 title claims 2
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical class CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims description 28
- 125000004432 carbon atom Chemical group C* 0.000 claims description 22
- 150000003839 salts Chemical class 0.000 claims description 21
- 239000002253 acid Substances 0.000 claims description 14
- 125000000217 alkyl group Chemical group 0.000 claims description 14
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 9
- 239000001257 hydrogen Substances 0.000 claims description 9
- 229910052739 hydrogen Inorganic materials 0.000 claims description 9
- 238000000034 method Methods 0.000 claims description 8
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims description 5
- 125000003545 alkoxy group Chemical group 0.000 claims description 5
- 125000003884 phenylalkyl group Chemical group 0.000 claims description 5
- 238000003797 solvolysis reaction Methods 0.000 claims description 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
- 125000003342 alkenyl group Chemical group 0.000 claims description 4
- 229910052736 halogen Inorganic materials 0.000 claims description 3
- 150000002367 halogens Chemical class 0.000 claims description 3
- 238000002360 preparation method Methods 0.000 claims description 3
- QRDSDKAGXMWBID-UHFFFAOYSA-N 5-azabicyclo[3.1.0]hexane Chemical class C1CCN2CC21 QRDSDKAGXMWBID-UHFFFAOYSA-N 0.000 claims description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 2
- 229910052799 carbon Inorganic materials 0.000 claims description 2
- 229910052757 nitrogen Inorganic materials 0.000 claims description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
- AICGDXIQDWDUFG-UHFFFAOYSA-N 3-methyl-3-azabicyclo[3.1.0]hexane-1-carboxylic acid Chemical compound C1N(C)CC2CC21C(O)=O AICGDXIQDWDUFG-UHFFFAOYSA-N 0.000 claims 2
- MNWFXJYAOYHMED-UHFFFAOYSA-N heptanoic acid Chemical class CCCCCCC(O)=O MNWFXJYAOYHMED-UHFFFAOYSA-N 0.000 claims 1
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims 1
- 229940126601 medicinal product Drugs 0.000 claims 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 15
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 13
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 8
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- 150000002431 hydrogen Chemical class 0.000 description 4
- 150000002825 nitriles Chemical class 0.000 description 4
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 125000004453 alkoxycarbonyl group Chemical group 0.000 description 3
- 150000001733 carboxylic acid esters Chemical class 0.000 description 3
- 239000003054 catalyst Substances 0.000 description 3
- 150000002148 esters Chemical class 0.000 description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- 239000007789 gas Substances 0.000 description 3
- 229910052500 inorganic mineral Inorganic materials 0.000 description 3
- 239000011707 mineral Substances 0.000 description 3
- 235000010755 mineral Nutrition 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- 229920006395 saturated elastomer Polymers 0.000 description 3
- LPKISEDDMGRGBI-UHFFFAOYSA-N 3-(2-hydroxyethyl)-3-azabicyclo[3.1.0]hexane-1-carbonitrile Chemical compound C1N(CCO)CC2CC21C#N LPKISEDDMGRGBI-UHFFFAOYSA-N 0.000 description 2
- ZMMHJHWUKIEUJA-UHFFFAOYSA-N 3-azabicyclo[3.1.0]hexane-1-carbonitrile Chemical compound C1NCC2(C#N)C1C2 ZMMHJHWUKIEUJA-UHFFFAOYSA-N 0.000 description 2
- BOHSMHNKEIRAEH-UHFFFAOYSA-N 3-benzyl-3-azabicyclo[3.1.0]hexane-1-carbonitrile Chemical compound C1C2(C#N)CC2CN1CC1=CC=CC=C1 BOHSMHNKEIRAEH-UHFFFAOYSA-N 0.000 description 2
- RSRCMBRDWDMVCC-UHFFFAOYSA-N 3-methyl-3-azabicyclo[3.1.0]hexane-1-carbonitrile Chemical group C1N(C)CC2CC21C#N RSRCMBRDWDMVCC-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical compound CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 2
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 2
- 238000006555 catalytic reaction Methods 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 125000004093 cyano group Chemical group *C#N 0.000 description 2
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 2
- 206010015037 epilepsy Diseases 0.000 description 2
- -1 ethyl hexane-1-carboximidate dihydrochloride Chemical compound 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- MUBZPKHOEPUJKR-UHFFFAOYSA-M oxalate(1-) Chemical compound OC(=O)C([O-])=O MUBZPKHOEPUJKR-UHFFFAOYSA-M 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 235000011121 sodium hydroxide Nutrition 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- FRASJONUBLZVQX-UHFFFAOYSA-N 1,4-naphthoquinone Chemical compound C1=CC=C2C(=O)C=CC(=O)C2=C1 FRASJONUBLZVQX-UHFFFAOYSA-N 0.000 description 1
- KYARBIJYVGJZLB-UHFFFAOYSA-N 7-amino-4-hydroxy-2-naphthalenesulfonic acid Chemical compound OC1=CC(S(O)(=O)=O)=CC2=CC(N)=CC=C21 KYARBIJYVGJZLB-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- 208000018152 Cerebral disease Diseases 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
- 208000023105 Huntington disease Diseases 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 229910001854 alkali hydroxide Inorganic materials 0.000 description 1
- 229910001860 alkaline earth metal hydroxide Inorganic materials 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 150000001413 amino acids Chemical class 0.000 description 1
- 238000007098 aminolysis reaction Methods 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 230000002490 cerebral effect Effects 0.000 description 1
- 208000026106 cerebrovascular disease Diseases 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
- OTLSHNPOYOUQDC-UHFFFAOYSA-N ethyl 3-methyl-3-azabicyclo[3.1.0]hexane-1-carboximidate;dihydrochloride Chemical compound Cl.Cl.C1N(C)CC2(C(=N)OCC)C1C2 OTLSHNPOYOUQDC-UHFFFAOYSA-N 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- VZCYOOQTPOCHFL-OWOJBTEDSA-M fumarate(1-) Chemical compound OC(=O)\C=C\C([O-])=O VZCYOOQTPOCHFL-OWOJBTEDSA-M 0.000 description 1
- 229960003692 gamma aminobutyric acid Drugs 0.000 description 1
- BTCSSZJGUNDROE-UHFFFAOYSA-N gamma-aminobutyric acid Chemical compound NCCCC(O)=O BTCSSZJGUNDROE-UHFFFAOYSA-N 0.000 description 1
- 238000007327 hydrogenolysis reaction Methods 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 125000001841 imino group Chemical group [H]N=* 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 230000003472 neutralizing effect Effects 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 230000003285 pharmacodynamic effect Effects 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 238000006894 reductive elimination reaction Methods 0.000 description 1
- 201000000980 schizophrenia Diseases 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- RWRDLPDLKQPQOW-UHFFFAOYSA-N tetrahydropyrrole Substances C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/52—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring condensed with a ring other than six-membered
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Diabetes (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Medicinal Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Hematology (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Indole Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH1564375 | 1975-12-02 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2653251A1 true DE2653251A1 (de) | 1977-06-08 |
Family
ID=4410767
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19762653251 Withdrawn DE2653251A1 (de) | 1975-12-02 | 1976-11-24 | Azabicyclo eckige klammer auf 3.1.o eckige klammer zu hexan-derivate, ihre herstellung und verwendung |
Country Status (12)
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0007652A1 (en) * | 1978-06-27 | 1980-02-06 | Shell Internationale Researchmaatschappij B.V. | Derivatives of 3-azabicyclo(3.1.0)hexane and a process for their preparation |
| EP0008813A1 (en) * | 1978-07-06 | 1980-03-19 | Shell Internationale Researchmaatschappij B.V. | Processes for the preparation of 3-azabicyclo(3.1.0)hexane derivatives |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA1121356A (en) * | 1979-11-16 | 1982-04-06 | Janet A. Day | Azabicyclohexane derivatives, a process for preparing them, pollen-suppressing compositions, a method of producing f.sub.1 hybrid seed, and seed thus produced |
| DE3324263A1 (de) * | 1983-07-06 | 1985-01-17 | Hoechst Ag, 6230 Frankfurt | Derivate der 2-azabicyclo(3.1.0)hexan-3-carbonsaeure, verfahren zu ihrer herstellung, diese enthaltende mittel und deren verwendung sowie 2-azabicyclo(3.1.0)hexan-derivate als zwischenprodukte und verfahren zu deren herstellung |
| US20020111496A1 (en) * | 2001-02-02 | 2002-08-15 | Horenstein Benjamin A. | Inhibitors of glycosyltransferase enzymes |
| US7056864B2 (en) * | 2002-07-11 | 2006-06-06 | The United States Of America As Represented By The Secretary Of Agriculture | Methods of reducing pests by use of halogen substituted ethanol |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1054088B (de) * | 1957-05-17 | 1959-04-02 | Merck Ag E | Verfahren zur Herstellung von Dehydrierungsprodukten des Piperidins und Pyrrolidins |
-
1976
- 1976-11-23 DK DK527476A patent/DK527476A/da unknown
- 1976-11-23 FI FI763359A patent/FI763359A7/fi not_active Application Discontinuation
- 1976-11-24 DE DE19762653251 patent/DE2653251A1/de not_active Withdrawn
- 1976-11-25 SE SE7613182A patent/SE7613182L/xx unknown
- 1976-11-26 NL NL7613205A patent/NL7613205A/xx not_active Application Discontinuation
- 1976-11-30 GB GB49833/76A patent/GB1562831A/en not_active Expired
- 1976-11-30 ES ES453803A patent/ES453803A1/es not_active Expired
- 1976-11-30 BE BE172868A patent/BE848936A/xx unknown
- 1976-12-01 JP JP51143537A patent/JPS5268173A/ja active Pending
- 1976-12-02 FR FR7636297A patent/FR2333508A1/fr not_active Withdrawn
- 1976-12-02 AU AU20197/76A patent/AU2019776A/en not_active Expired
-
1978
- 1978-07-03 US US05/921,512 patent/US4235921A/en not_active Expired - Lifetime
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0007652A1 (en) * | 1978-06-27 | 1980-02-06 | Shell Internationale Researchmaatschappij B.V. | Derivatives of 3-azabicyclo(3.1.0)hexane and a process for their preparation |
| EP0008813A1 (en) * | 1978-07-06 | 1980-03-19 | Shell Internationale Researchmaatschappij B.V. | Processes for the preparation of 3-azabicyclo(3.1.0)hexane derivatives |
Also Published As
| Publication number | Publication date |
|---|---|
| SE7613182L (sv) | 1977-06-02 |
| JPS5268173A (en) | 1977-06-06 |
| DK527476A (da) | 1977-06-03 |
| NL7613205A (nl) | 1977-06-06 |
| FI763359A7 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1977-06-03 |
| FR2333508A1 (fr) | 1977-07-01 |
| ES453803A1 (es) | 1978-01-01 |
| AU2019776A (en) | 1978-06-08 |
| GB1562831A (en) | 1980-03-19 |
| BE848936A (fr) | 1977-05-31 |
| US4235921A (en) | 1980-11-25 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8139 | Disposal/non-payment of the annual fee |