CH619705A5 - Process for the preparation of N-formyl-7-oxocyclohexano- or -8-oxocycloheptano[b]thiophene-4-amines - Google Patents
Process for the preparation of N-formyl-7-oxocyclohexano- or -8-oxocycloheptano[b]thiophene-4-amines Download PDFInfo
- Publication number
- CH619705A5 CH619705A5 CH1016878A CH1016878A CH619705A5 CH 619705 A5 CH619705 A5 CH 619705A5 CH 1016878 A CH1016878 A CH 1016878A CH 1016878 A CH1016878 A CH 1016878A CH 619705 A5 CH619705 A5 CH 619705A5
- Authority
- CH
- Switzerland
- Prior art keywords
- acid
- formula
- preparation
- formyl
- thiophene
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims abstract description 10
- 238000002360 preparation method Methods 0.000 title claims description 8
- WGLPBDUCMAPZCE-UHFFFAOYSA-N Trioxochromium Chemical compound O=[Cr](=O)=O WGLPBDUCMAPZCE-UHFFFAOYSA-N 0.000 claims abstract description 19
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 claims abstract description 18
- 239000007800 oxidant agent Substances 0.000 claims abstract description 8
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims abstract description 6
- 239000007864 aqueous solution Substances 0.000 claims abstract description 6
- 150000001875 compounds Chemical class 0.000 claims abstract description 6
- VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 claims abstract description 6
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 claims abstract description 3
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 claims abstract description 3
- 229910000147 aluminium phosphate Inorganic materials 0.000 claims abstract description 3
- SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 claims abstract description 3
- 229910017604 nitric acid Inorganic materials 0.000 claims abstract description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims description 7
- 239000001257 hydrogen Substances 0.000 claims description 7
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 5
- KELIOZMTDOSCMM-UHFFFAOYSA-N 2,3,3a,4-tetrahydro-1-benzothiophene Chemical class C1C=CC=C2SCCC21 KELIOZMTDOSCMM-UHFFFAOYSA-N 0.000 claims 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 abstract description 12
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 abstract description 9
- NDVLTYZPCACLMA-UHFFFAOYSA-N silver oxide Chemical compound [O-2].[Ag+].[Ag+] NDVLTYZPCACLMA-UHFFFAOYSA-N 0.000 abstract description 8
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 abstract description 6
- XMPZTFVPEKAKFH-UHFFFAOYSA-P ceric ammonium nitrate Chemical compound [NH4+].[NH4+].[Ce+4].[O-][N+]([O-])=O.[O-][N+]([O-])=O.[O-][N+]([O-])=O.[O-][N+]([O-])=O.[O-][N+]([O-])=O.[O-][N+]([O-])=O XMPZTFVPEKAKFH-UHFFFAOYSA-P 0.000 abstract description 6
- -1 hydroxymethylene group Chemical group 0.000 abstract description 5
- JHWIEAWILPSRMU-UHFFFAOYSA-N 2-methyl-3-pyrimidin-4-ylpropanoic acid Chemical compound OC(=O)C(C)CC1=CC=NC=N1 JHWIEAWILPSRMU-UHFFFAOYSA-N 0.000 abstract description 4
- 239000002253 acid Substances 0.000 abstract description 4
- 229910001923 silver oxide Inorganic materials 0.000 abstract description 4
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 abstract description 3
- 235000013877 carbamide Nutrition 0.000 abstract description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 abstract description 3
- 150000003585 thioureas Chemical class 0.000 abstract description 3
- 150000003672 ureas Chemical class 0.000 abstract description 3
- 241001465754 Metazoa Species 0.000 abstract description 2
- ZMZDMBWJUHKJPS-UHFFFAOYSA-M Thiocyanate anion Chemical compound [S-]C#N ZMZDMBWJUHKJPS-UHFFFAOYSA-M 0.000 abstract description 2
- 229910052783 alkali metal Inorganic materials 0.000 abstract description 2
- ZMZDMBWJUHKJPS-UHFFFAOYSA-N hydrogen thiocyanate Natural products SC#N ZMZDMBWJUHKJPS-UHFFFAOYSA-N 0.000 abstract description 2
- 229910052500 inorganic mineral Inorganic materials 0.000 abstract description 2
- 239000011707 mineral Substances 0.000 abstract description 2
- 150000003839 salts Chemical class 0.000 abstract description 2
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 abstract 1
- 230000007062 hydrolysis Effects 0.000 abstract 1
- 238000006460 hydrolysis reaction Methods 0.000 abstract 1
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 abstract 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 abstract 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- 125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 description 2
- 239000000284 extract Substances 0.000 description 2
- 229910052736 halogen Inorganic materials 0.000 description 2
- 150000002367 halogens Chemical class 0.000 description 2
- 150000002431 hydrogen Chemical group 0.000 description 2
- 230000003647 oxidation Effects 0.000 description 2
- 238000007254 oxidation reaction Methods 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- OVYSXAZBCBIOSB-UHFFFAOYSA-N n-(7-oxo-5,6-dihydro-4h-1-benzothiophen-4-yl)formamide Chemical compound O=CNC1CCC(=O)C2=C1C=CS2 OVYSXAZBCBIOSB-UHFFFAOYSA-N 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
Classifications
-
- 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
- C07D333/50—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
- C07D333/52—Benzo[b]thiophenes; Hydrogenated benzo[b]thiophenes
- C07D333/54—Benzo[b]thiophenes; Hydrogenated benzo[b]thiophenes with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the hetero ring
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23K—FODDER
- A23K20/00—Accessory food factors for animal feeding-stuffs
- A23K20/10—Organic substances
- A23K20/116—Heterocyclic compounds
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23K—FODDER
- A23K20/00—Accessory food factors for animal feeding-stuffs
- A23K20/10—Organic substances
- A23K20/116—Heterocyclic compounds
- A23K20/121—Heterocyclic compounds containing oxygen or sulfur as hetero atom
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23K—FODDER
- A23K20/00—Accessory food factors for animal feeding-stuffs
- A23K20/10—Organic substances
- A23K20/116—Heterocyclic compounds
- A23K20/137—Heterocyclic compounds containing two hetero atoms, of which at least one is nitrogen
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
-
- 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
- C07D333/50—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
- C07D333/52—Benzo[b]thiophenes; Hydrogenated benzo[b]thiophenes
- C07D333/54—Benzo[b]thiophenes; Hydrogenated benzo[b]thiophenes with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the hetero ring
- C07D333/56—Radicals substituted by oxygen atoms
-
- 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
- C07D333/50—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
- C07D333/52—Benzo[b]thiophenes; Hydrogenated benzo[b]thiophenes
- C07D333/62—Benzo[b]thiophenes; Hydrogenated benzo[b]thiophenes 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 carbon atoms of the hetero ring
-
- 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
- C07D333/50—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
- C07D333/52—Benzo[b]thiophenes; Hydrogenated benzo[b]thiophenes
- C07D333/62—Benzo[b]thiophenes; Hydrogenated benzo[b]thiophenes 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 carbon atoms of the hetero ring
- C07D333/66—Nitrogen atoms not forming part of a nitro radical
-
- 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
- C07D333/50—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
- C07D333/52—Benzo[b]thiophenes; Hydrogenated benzo[b]thiophenes
- C07D333/62—Benzo[b]thiophenes; Hydrogenated benzo[b]thiophenes 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 carbon atoms of the hetero ring
- C07D333/68—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
- C07D333/70—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen attached in position 2
-
- 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
- C07D333/50—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
- C07D333/78—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems condensed with rings other than six-membered or with ring systems containing such rings
- C07D333/80—Seven-membered rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Polymers & Plastics (AREA)
- Engineering & Computer Science (AREA)
- Animal Husbandry (AREA)
- Zoology (AREA)
- Food Science & Technology (AREA)
- Health & Medical Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Hematology (AREA)
- Obesity (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Diabetes (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)
- Fodder In General (AREA)
- Feed For Specific Animals (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Die Erfindung betrifft ein Verfahren zur Herstellung von N-Formyl-7-oxocyclohexano- oder -8-oxocycloheptano-25 [b]-thiophen-4-aminen der Formel:
R,
Worin Z für Wasserstoff oder Ci-Ct-Alkyl steht, Y Wasserstoff, Ci-Ci-Alkyl, Halogen, Cyano, Nitro, Acetyl, Acetylamino oder ein Rest der Formel Ri-NHCONH- ist und Ri Wasserstoff oder Ci-Ci-Alkyl bedeutet, dadurch gekennzeichnet, dass man ein Moläquivalent einer Verbindung der Formel:
(Ia)
oder
(IIa)
30
N-CHO
(i)
bzw.
45
(II)
55
60
worin Z für Wasserstoff oder Ci-Ct-Alkyl steht, Y Wasserstoff, Ci-C4-Alkyl, Halogen, Cyano, Nitro, Acetyl, Acetylamino oder ein Rest der Formel Ri-NHCONH- ist und Ri Wasserstoff oder Ci-Ci-Alkyl bedeutet. Das Verfahren ist dadurch gekennzeichnet, dass man ein Moläquivalent einer Verbindung der Formel:
worin U für-CH2— oder-CHOH— steht, bei einer Temperatur von 0 bis 100°C mit 2 bis 8 Moläquivalent a) Chromsäureanhydrid in Essigsäureanhydrid oder 65
b) Cer(IV)ammoniumnitrat, Silberoxid, Chromsäureanhydrid oder Natriumdichromat in Gegenwart einer wässrigen Lösung von Essigsäure, Acetonitril, Tetrahydrofuran, Dioxan,
N-CHO
(Ia)
oder
3
619 705
î1
N-CHO
worin U für-CHi- oder-CHOH- steht, bei einer Temperatur von 0 bis 1000 C mit 2 bis 8 Moläquivalent a) Chromsäureanhydrid in Essigsäureanhydrid oder 15
b) Cer(IV)-ammoniumnitrat, Silberoxid, Chromsäureanhydrid oder Natriumdichromat in Gegenwart einer wässrigen Lösung von Essigsäure, Acetonitril, Tetrahydrofuran, Dioxan, Dimethoxyäthan oder Diäthylenglykoldimethyläther oxidiert und bei Verwendung von Chromsäureanhydrid in 20 Essigsäureanhydrid als Oxidationsmittel anschliessend hydro-lysiert. Die wässrige Lösung kann Salpetersäure, Phosphorsäure oder Perchlorsäure enthalten.
Das erfindungsgemässe Verfahren wird vorzugsweise unter Verwendung von 4 bis 5 Moläquivalent eines Oxidationsmittels 2s der genannten Art sowie vorzugsweise bei einer Temperatur von 20 bis 60 °C durchgeführt.
Nach Beendigung der Oxidationsstufe können die erhaltenen Oxoverbindungen in verdünnter Mineralsäure hydrolysiert werden. Die auf diese Weise erhaltenen Säuresalze der Amine 30 können mit einem Alkalimetallcyanat oder -thiocyanat bei einem pH-Wert von 5 bis 7 umgesetzt werden, wodurch man die entsprechenden Harnstoffe oder Thioharnstoffe erhält, die sich durch eine wachstumsfördernde Wirkung insbesondere bei Tieren auszeichnen. Die erfindungsgemäss herstellbaren Ver- 35
bindungen sind demzufolge wertvolle Zwischenprodukte zur Herstellung solcher Cycloalkano-[b]-thienylharnstoffe. Die Erfindung wird anhand der Beispiele weiter erläutert.
Beispiel 1
Herstellung von N-Formyl-4,5,6,7-tetrahydro-7-oxobenzo-[b]-thiophen-4-amin Man löst 6 g N-Formyl-4,5,6,7-tetrahydrobenzo-[b]-thiophen-4-amin in 375 ml 50%iger wässriger Essigsäure und gibt unter Rühren im Verlaufe von 10 Minuten bei einer Temperatur von 25 bis 35°C portionsweise 75 g Cer(IV)-ammo-niumnitrat zu. Die Lösung wird weitere 5 Minuten lang gerührt und dann mit 10 ml Wasser versetzt. Hierauf wird die Lösung zweimal mit Methylenchlorid (450 ml und 350 ml) extrahiert, worauf man die vereinigten Extrakte mit 100 ml Wasser wäscht. Der organische Extrakt wird im Vakuum zur Trockne eingedampft. Durch Umkristallisieren des dabei erhaltenen Rückstands erhält man N-Formyl-Tetrahydro-7-oxobenzo-[b]-thio-phen-4-amin mit einem Schmelzpunkt von 118 bis 120°C (Zersetzung).
Wenn man Cer(IV)-ammoniumnitrat durch Silberoxid, Chromsäureanhydrid oder Natriumdichromat ersetzt, so erhält man ebenfalls die oben angegebene 7-Oxoverbindung. Auch die Umsetzung mit Chromsäureanhydrid in Essigsäureanhydrid ergibt die 7-Oxoverbindung. Die oben erwähnten 7-Oxover-bindungen kann man ferner in ähnlicher Weise durch Oxidation der entsprechenden 7-HydroxyVerbindungen herstellen.
Beispiel 2
Herstellung von N-Formyl-8-oxocycloheptano-[b]-thiophen-4-amin Nach dem in Beispiel 1 beschriebenen Verfahren behandelt man N-Formylcycloheptano-[b]-thiophen-4-amin, das bei 164 bis 166 °C schmilzt, mit 4 Äquivalent Cer(IV)-ammonium-nitrat, wodurch man die im Titel genannte Verbindung erhält.
B
Claims (3)
- 6197052PATENTANSPRÜCHE 1. Verfahren zur Herstellung von N-Formyl-7-oxo-cyclo-hexano- oder -8-oxocycloheptano-[b]-thiophen-4-aminen der Formel:FLN-CHO(I)bzw.Dimethoxyäthan oder Diäthylenglykoldimethvläther oxidiert und bei Verwendung von Chromsäureanhydrid in Essigsäureanhydrid als Oxidationsmittel anschliessend hydroly-siert.
- 2. Verfahren nach Anspruch 1, dadurch gekennzeichnet,dass die wässrige Lösung Salpetersäure, Phosphorsäure oder Perchlorsäure enthält.3.Verfahren nach Anspruch 1 oder 2, dadurch gekennzeichnet, dass man 4 bis 5 Moläquivalent Oxidationsmittel verwendet und bei einer Temperatur im Bereich von 20 bis 60 °C arbeitet.
- 4. Verfahren nach Anspruch 1 oder 2 zur Herstellung von Verbindungen der Formel I, worin Ri, Y und Z Wasserstoff bedeuten.15(II)20Die Herstellung von Tetrahydrobenzothiophenderivaten ist aus den US-PS Nr. 3 989 505, 3 776 924 und 3 998 959 bekannt.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US43682774A | 1974-01-25 | 1974-01-25 | |
| US43682674A | 1974-01-25 | 1974-01-25 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH619705A5 true CH619705A5 (en) | 1980-10-15 |
Family
ID=27031116
Family Applications (4)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH87775A CH619703A5 (en) | 1974-01-25 | 1975-01-24 | Process for the preparation of novel optionally ring-substituted cycloalkano[b]thiophene ureas or thioureas and use thereof |
| CH1016678A CH619704A5 (en) | 1974-01-25 | 1978-09-29 | Process for the preparation of novel optionally ring-substituted cycloalkano[b]thiophene ureas or thioureas and use thereof |
| CH1016878A CH619705A5 (en) | 1974-01-25 | 1978-09-29 | Process for the preparation of N-formyl-7-oxocyclohexano- or -8-oxocycloheptano[b]thiophene-4-amines |
| CH1016778A CH619949A5 (en) | 1974-01-25 | 1978-09-29 | Process for the preparation of novel 7- or 8-oxo-cycloalkano[b]thien-4-ylureas and use thereof |
Family Applications Before (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH87775A CH619703A5 (en) | 1974-01-25 | 1975-01-24 | Process for the preparation of novel optionally ring-substituted cycloalkano[b]thiophene ureas or thioureas and use thereof |
| CH1016678A CH619704A5 (en) | 1974-01-25 | 1978-09-29 | Process for the preparation of novel optionally ring-substituted cycloalkano[b]thiophene ureas or thioureas and use thereof |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH1016778A CH619949A5 (en) | 1974-01-25 | 1978-09-29 | Process for the preparation of novel 7- or 8-oxo-cycloalkano[b]thien-4-ylureas and use thereof |
Country Status (21)
| Country | Link |
|---|---|
| JP (1) | JPS51125069A (de) |
| AT (1) | AT353590B (de) |
| CA (1) | CA1060899A (de) |
| CH (4) | CH619703A5 (de) |
| CS (1) | CS195276B2 (de) |
| DD (4) | DD125213A5 (de) |
| DE (1) | DE2501788C2 (de) |
| DK (1) | DK22775A (de) |
| ES (1) | ES434095A1 (de) |
| FR (1) | FR2333801A1 (de) |
| GB (1) | GB1499582A (de) |
| IE (1) | IE42039B1 (de) |
| IL (1) | IL46375A (de) |
| IN (1) | IN141050B (de) |
| IT (1) | IT1035548B (de) |
| LU (1) | LU71711A1 (de) |
| NL (1) | NL7500845A (de) |
| PH (1) | PH14544A (de) |
| SE (1) | SE421617B (de) |
| TR (1) | TR18381A (de) |
| YU (1) | YU36721B (de) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3994924A (en) * | 1975-11-04 | 1976-11-30 | American Cyanamid Company | 4,5,6,7-Tetra hydro-7-oxobenzo(B)thien-4-yl isocyanate and isothiocyanate |
| FR2430231A1 (fr) * | 1978-07-04 | 1980-02-01 | American Cyanamid Co | Tetrahydrobenzo(b)thienyl-4 urees et leur utilisation pour favoriser la pousse de la laine chez les animaux a toison |
| JPS6169772A (ja) * | 1984-12-04 | 1986-04-10 | アメリカン サイアナミッド カンパニ− | テトラヒドロベンゾ〔ｂ〕チオフエン誘導体、その製法及び動物成長促進法 |
| EP1801098A1 (de) | 2005-12-16 | 2007-06-27 | Merck Sante | 2-Adamantylharnstoff Derivative als selektive 11B-HSD1 Inhibitoren |
-
1974
- 1974-12-31 CA CA217,189A patent/CA1060899A/en not_active Expired
-
1975
- 1975-01-01 IL IL46375A patent/IL46375A/xx unknown
- 1975-01-02 IN IN20/CAL/75A patent/IN141050B/en unknown
- 1975-01-06 IE IE26/75A patent/IE42039B1/en unknown
- 1975-01-10 PH PH16699A patent/PH14544A/en unknown
- 1975-01-14 GB GB1592/75A patent/GB1499582A/en not_active Expired
- 1975-01-17 DE DE2501788A patent/DE2501788C2/de not_active Expired
- 1975-01-21 AT AT42675A patent/AT353590B/de not_active IP Right Cessation
- 1975-01-22 CS CS75448A patent/CS195276B2/cs unknown
- 1975-01-23 LU LU71711A patent/LU71711A1/xx unknown
- 1975-01-23 FR FR7502174A patent/FR2333801A1/fr active Granted
- 1975-01-24 DD DD192557A patent/DD125213A5/xx unknown
- 1975-01-24 YU YU0172/75A patent/YU36721B/xx unknown
- 1975-01-24 SE SE7500793A patent/SE421617B/xx not_active IP Right Cessation
- 1975-01-24 DD DD183814A patent/DD119790A5/xx unknown
- 1975-01-24 DD DD192555A patent/DD125211A5/xx unknown
- 1975-01-24 DK DK22775*BA patent/DK22775A/da not_active Application Discontinuation
- 1975-01-24 CH CH87775A patent/CH619703A5/de not_active IP Right Cessation
- 1975-01-24 NL NL7500845A patent/NL7500845A/xx not_active Application Discontinuation
- 1975-01-24 IT IT47844/75A patent/IT1035548B/it active
- 1975-01-24 ES ES434095A patent/ES434095A1/es not_active Expired
- 1975-01-24 DD DD192556A patent/DD125212A5/xx unknown
- 1975-01-25 JP JP50010184A patent/JPS51125069A/ja active Granted
- 1975-01-27 TR TR18381A patent/TR18381A/xx unknown
-
1978
- 1978-09-29 CH CH1016678A patent/CH619704A5/de not_active IP Right Cessation
- 1978-09-29 CH CH1016878A patent/CH619705A5/de not_active IP Right Cessation
- 1978-09-29 CH CH1016778A patent/CH619949A5/de not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| JPS51125069A (en) | 1976-11-01 |
| AT353590B (de) | 1979-11-26 |
| DD125212A5 (de) | 1977-04-06 |
| GB1499582A (en) | 1978-02-01 |
| NL7500845A (nl) | 1975-07-29 |
| CS195276B2 (en) | 1980-01-31 |
| IL46375A0 (en) | 1975-04-25 |
| DE2501788C2 (de) | 1984-11-08 |
| FR2333801B1 (de) | 1982-07-09 |
| CA1060899A (en) | 1979-08-21 |
| IN141050B (de) | 1977-01-15 |
| IE42039L (en) | 1975-07-25 |
| JPS6133830B2 (de) | 1986-08-04 |
| DE2501788A1 (de) | 1975-07-31 |
| IL46375A (en) | 1982-04-30 |
| CH619949A5 (en) | 1980-10-31 |
| YU36721B (en) | 1984-08-31 |
| SE421617B (sv) | 1982-01-18 |
| DD125213A5 (de) | 1977-04-06 |
| CH619703A5 (en) | 1980-10-15 |
| IE42039B1 (en) | 1980-05-21 |
| YU17275A (en) | 1982-06-18 |
| ES434095A1 (es) | 1977-05-16 |
| FR2333801A1 (fr) | 1977-07-01 |
| CH619704A5 (en) | 1980-10-15 |
| IT1035548B (it) | 1979-10-20 |
| DD119790A5 (de) | 1976-05-12 |
| DK22775A (de) | 1975-09-15 |
| DD125211A5 (de) | 1977-04-06 |
| SE7500793L (de) | 1975-07-28 |
| AU7691574A (en) | 1976-07-01 |
| LU71711A1 (de) | 1975-06-24 |
| TR18381A (tr) | 1977-05-01 |
| PH14544A (en) | 1981-09-24 |
| ATA42675A (de) | 1979-04-15 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PL | Patent ceased | ||
| PL | Patent ceased |