DE1793561A1 - Hydrazone compounds and processes for their preparation - Google Patents
Hydrazone compounds and processes for their preparationInfo
- Publication number
- DE1793561A1 DE1793561A1 DE19641793561 DE1793561A DE1793561A1 DE 1793561 A1 DE1793561 A1 DE 1793561A1 DE 19641793561 DE19641793561 DE 19641793561 DE 1793561 A DE1793561 A DE 1793561A DE 1793561 A1 DE1793561 A1 DE 1793561A1
- Authority
- DE
- Germany
- Prior art keywords
- lower alkyl
- hydrogen
- processes
- preparation
- general formula
- 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.)
- Pending
Links
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
- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/10—Indoles; Hydrogenated indoles with substituted hydrocarbon radicals attached to carbon atoms of the hetero ring
- C07D209/18—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
-
- 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
- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/10—Indoles; Hydrogenated indoles with substituted hydrocarbon radicals attached to carbon atoms of the hetero ring
- C07D209/12—Radicals substituted by oxygen atoms
-
- 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
- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/10—Indoles; Hydrogenated indoles with substituted hydrocarbon radicals attached to carbon atoms of the hetero ring
- C07D209/18—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D209/26—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals with an acyl radical attached to the ring nitrogen atom
-
- 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
- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/10—Indoles; Hydrogenated indoles with substituted hydrocarbon radicals attached to carbon atoms of the hetero ring
- C07D209/18—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D209/26—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals with an acyl radical attached to the ring nitrogen atom
- C07D209/28—1-(4-Chlorobenzoyl)-2-methyl-indolyl-3-acetic acid, substituted in position 5 by an oxygen or nitrogen atom; Esters thereof
-
- 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
- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/30—Indoles; Hydrogenated indoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to carbon atoms of the hetero ring
- C07D209/32—Oxygen atoms
- C07D209/36—Oxygen atoms in position 3, e.g. adrenochrome
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Indole Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Plural Heterocyclic Compounds (AREA)
- Enzymes And Modification Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Description
DR-ING. WALTER ABITZ DR. DIETER MORFDR-ING. WALTER ABITZ DR. DIETER MORF
PatentanwältePatent attorneys
8 München 27, Pienzenauersfraße Telefon 483225 und 486415 Telegramme: Chemindus München8 Munich 27, Pienzenauersfraße Telephone 483225 and 486415 Telegrams: Chemindus Munich
26. Februar 196926th February 1969
11 974 (M 72 878) Λ Λ 11 974 (M 72 878) Λ Λ
P 16 95 396· 1P 16 95 396 1
TrennanmeldungSeparate registration
MERCK & CO., IKC. Rahway, New Jersey 07065, V. St. A.MERCK & CO., IKC. Rahway, New Jersey 07065, V. St. A.
Hydraionverbindungen und Verfahren zu deren HerstellungHydraion compounds and processes for their preparation
Die Erfindung betrifft neue Hydrazone der allgemeinen FormelThe invention relates to new hydrazones of the general formula
worin bedeutenin which mean
R1 gegebenenfalls substituiertes Phenyl, Rg Wasserstoff oder niedriges Alkyl, PU Wasserstoff oder niedriges Alkyl»R 1 optionally substituted phenyl, Rg hydrogen or lower alkyl, PU hydrogen or lower alkyl »
■ - .1 109884/1822 ■ - .1 109884/1822
»AD OfilGINAL“AD OfilGINAL
Xl 974Xl 974
Rc niedriges Alkoxy* Dlalkylamino* . X CHO, CH(ORx)2, CHgOH, CH2ORx* COOH oder CU und R^ niedriges Alkyl* Aralkyl oder Trityl.Rc lower alkoxy * dialkylamino *. X CHO, CH (OR x ) 2 , CHgOH, CH 2 OR x * COOH or CU and R ^ lower alkyl * aralkyl or trityl.
Wenn der Rest R1 ein substituierter Phenylrest 1st» so kann er s. B. durch einen Kohlenwasserstoffrest substituiert sein* Vorzugsweise ist aber der Substltuent ein anderer Reist· Die·* ser Substituent kann eine Hydroxygruppe oder eine verätherte Hydroxygruppe (Hydrooarbyloxygruppe) sein« wie ein niedriger Alkoxy-* Aryloxy» oder Aralkoxyrest« z. B. Methoxy, ftthoxy* Isopropoxy* Propoxy, Allyloxy* Phenoxy* Btnzyloxy» Balogenbenzyloxy* niedrig-Alkoxybenzyloxy. Br kann auch eine Mitrogruppe* ein Halogenatom, eine Aminogruppe oder substituierte Aminogruppe bedeuten* für welche typische Beispiele Aoylatnino, Amlnoxyd, Ketimine. Urethane* niedrig-Alkylasjino, niedrig-Dialkylamino, Araidin, acyIierte Amidine* Hydrazin oder substituierte Hydrazine* Alkoxyämine und sulfoniert« Amine sind. Auseerdem kann dieser Substituent ein Mercapto- oder substituierter Meroaptorest sein* z. B. Alkylthio, wie Methylthlo* Äfchylthio oder Propylthio, Arylthio oder Aralkylthio, x. B. Benzylthlo oder Phenylthio. Er' kann welter bedeuten Halogenalkyl* beispielsweise Tri fluorine thy 1, Trifluoräthyl, P«rfluoräthyl oder ß-Chloräthyl, Acyl, beispielsweiee Acetyl, Propionyl* Benzoyl* Phenylacetyl oder Trifluoraoetyl, Halogenalkoxy, oder Halogenalkylthio. Weitere Subetltuenten des Phenylrestes sind Sulfenyl* BenzylthiomethyI, Cyano* Sulfonamide, Dialkylsulfonanldo* Carboxy oder ein Derivat hiervon, beispielsweise ein Alkallsals oder ein niedriger Alkylester des Carboxyre-3tes, ein Aldehyd* AsId* Araid, Hydrasld* Acetal oder fhioacetal· In den bevorzugten Verbindungen befindet sioh der Bub» stituent in der p-Steilung des Phenylrestes.If the radical R 1 is a substituted phenyl radical "it can be substituted, for example, by a hydrocarbon radical * but the substituent is preferably another rice * This substituent can be a hydroxyl group or an etherified hydroxyl group (hydrooarbyloxy group)" such as a lower alkoxy * aryloxy "or aralkoxy" z. B. methoxy, ftthoxy * isopropoxy * propoxy, allyloxy * phenoxy * benzyloxy »balogenbenzyloxy * lower-alkoxybenzyloxy. Br can also mean a mitro group * a halogen atom, an amino group or substituted amino group * for which typical examples aoylatnino, amine oxide, ketimine. Urethanes * lower-alkylasjino, lower-dialkylamino, araidin, acylated amidines * hydrazine or substituted hydrazines * alkoxyamines and sulfonated «amines are. In addition, this substituent can be a mercapto or substituted meroapto radical * z. B. alkylthio, such as methylthlo * Äfchylthio or propylthio, arylthio or aralkylthio, x. B. benzylthlo or phenylthio. It can also mean haloalkyl, for example tri fluorine thy 1, trifluoroethyl, p-rfluoroethyl or β-chloroethyl, acyl, for example acetyl, propionyl, benzoyl, phenylacetyl or trifluoroethyl, haloalkoxy, or haloalkylthio. Further substituents of the phenyl radical are sulfenyl * benzylthiomethyl, cyano * sulfonamides, dialkylsulfonanldo * carboxy or a derivative thereof, for example an alkali metal or a lower alkyl ester of the carboxyre-3th, an aldehyde * AsId * Araid, hydrasld * acetal or the preferred compounds the substituent is located in the p-position of the phenyl radical.
- 2 10 98 8 4/1822 »AD OR(GfNAL- 2 10 98 8 4/1822 »AD OR (GfNAL
11 97*11 97 *
Der' Beet R^ kann Wasserstoff sein; es ist Jedoch bevorzugt, dass in dieser Stellung ein KohlenwaseeretQffreet mit weniger als 9 Kohlenstoffatomen steht. Niedrige Alkylreste, beispielsweise Methyl» Xthyl, Propyl oder Butyl sind an eufriedensteilendeten. The 'bed R ^ can be hydrogen; However, it is preferred that in this position a coal-water tar with less stands as 9 carbon atoms. Lower alkyl groups, for example Methyl, ethyl, propyl, or butyl are among those who are satisfied.
R, in der obigen Formel kann Wasserstoff oder niedriges Alkyl, beispielsweise Methyl» Xthyl oder Propyl« sein.R, in the above formula can be hydrogen or lower alkyl, for example, methyl "Xthyl or Propyl" be.
Beispiele für R5 (niedriges Alkoxy} sind Methoxy, Xthoxy, !«Prop oxy. Beispiele für R~ - Dlalkylamlno sind Dimethylamine, Di* Kthylamino, Xthyl-sek.-butylamino oder Dileopropylamlno.Examples of R 5 (lower alkoxy) are methoxy, xthoxy,! «Propoxy. Examples of R ~ - alkylamino are dimethylamines, diethylamino, ethylsec.-butylamino or dileopropylamino.
Die neuen Verbindungen erhalt man» indee man eine Verbindung der allgemeinen FormelThe new connections are obtained “by establishing a connection the general formula
mit einer Verbindung der allgemeinen Formelwith a compound of the general formula
CH2-CH-XCH 2 -CH-X
in welchen R1, R2, R,, R5 und X dl» vorher genannte Bedeutung haben» umsetst und dabei das entstehend·. Wasser aus dem System entfernt·in which R 1 , R 2 , R ,, R 5 and X dl »have the meaning given above» implements the resulting ·. Removed water from the system
109884/1822109884/1822
dukte für dl« Herstellung von Indolylverbindungen der allge* meinen Formel ■ .products for dl «production of indolyl compounds in general * my formula ■.
worin R1, R2, R,, R. und X die vorher genannte Bedeutung ha· Den« Diese Verbindungen sind wertvolle Arzneimittel gegen ent« sttndllche und degenerative Störungen des Bewegungsapparates und dergleichen.where R 1 , R 2 , R 1, R and X have the meaning given above. These compounds are valuable medicaments against developing and degenerative disorders of the musculoskeletal system and the like.
GH,GH,
CO8HCO 8 H
109884/1822109884/1822
•AD Oft,G!NAL• AD Often, G! NAL
Il 974Il 974
In einen 500-ml-Dreihalsrundkolben, ausgerüstet mit einen mechanischen Rührer und einem Dean-Stark-Wasserabsohelder, werden 27,6 g (0,10 Mol) des oben gekennzeichneten Hydrazins, 275 cnr Toluol und 20 oar Lävulinsäure vorgelegt. Die Mischung wird unter Rückfluss erhitzt und ca. 1,2 oar dabei gebildetes Was« ser werden entfernt. Dann werden in den Wasserabscheider nach Dean-Stark Siebe gegeben, um die lotsten Spuren an HgO zu entfernen (uesamtrückflussdauer oa» 5 Stunden).In a 500 ml three-necked round bottom flask equipped with a mechanical Stirrer and a Dean-Stark water absorber 27.6 g (0.10 mole) of the hydrazine identified above, 275 cnr Submitted toluene and 20 oar levulinic acid. The mix will heated under reflux and about 1.2 oar formed water « ser will be removed. Sieves are then placed in the Dean-Stark water separator in order to remove the most loose traces of HgO (Total reflux time or the like »5 hours).
Das Toluol wird im Vakuum entfernt und das Ol wird in 100 car Äthylacetat aufgelöst und dazu wird bis zum Trübungspunkt Petroläther gegeben. Beim Versetzen mit Impfkristallen aus N-o> (p-Chlorbenzoyl)-p-methoxyphGnyl-hydrazon und Kratzen an der OQfässwand und nach Zugabe von weiterem Petrolttther wird das Ul kräftig extrahiert und das Produkt kristallisiert. Die Gesamtmenge an Petroläther beträgt etwa 1 Liter. Die Kristalle werden filtriert, mit Petroläther gewaschen und im Vakuum bei 45 0C getrocknet, wobei man 29 g (79 £) mit einem Schmelzpunkt von 83 bis 92 0C erhält, die durch Infrarotanaljse als identisch mit N-a-ip-ChlorbenzoylJ-p-raethoxyphenyl-hydreson identifiziert wurden.The toluene is removed in vacuo and the oil is dissolved in 100 carbons of ethyl acetate and petroleum ether is added to the cloud point. When adding seed crystals from No> (p-chlorobenzoyl) -p-methoxyphGnyl-hydrazone and scratching the wall of the container and after adding more petroleum ether, the oil is vigorously extracted and the product crystallized. The total amount of petroleum ether is about 1 liter. The crystals are filtered, washed with petroleum ether and dried in vacuo at 45 0 C., are obtained with a melting point of 83-92 0 C 29 g (79 £), by Infrarotanaljse as identical with Na-IP ChlorbenzoylJ-p- raethoxyphenyl-hydreson were identified.
Reinigung Cleaning
29 g i!-a-(p-Chlorbenzoyl)-p-methoxyphenyl-nydrazon werden In 600 cm5 Äthylaoetat bei 50 0C aufgelöst und dazu werden 100 cm-5 Petroläther gegeben. Die klare Lösung wird mit Impfkristallen versetat und gekratzt und dann bei Raumtemperatur ge* rührt. Nach 4 Stunden werden die. Kristalle abfiltriert, dreimal mit einer Mischung aus Äthylaoetat und Petroläther in Verhältnis I s 1 gewaschen und dann bis zur Oewiohtskonstani in Vakuum getrocknet, wobei man 20 g (69 %) mit einem Sohaelspunkt von 101 bis 10? 0C erhält.Gi 29! -A- (p-chlorobenzoyl) -p-methoxyphenyl-nydrazon are dissolved in 600 cm 5 Äthylaoetat at 50 0 C and to this are added 100 cm- 5 petroleum ether. The clear solution is treated with seed crystals and scratched and then stirred at room temperature. After 4 hours the. Crystals are filtered off, washed three times with a mixture of ethyl acetate and petroleum ether in a ratio of I s 1 and then dried in vacuo to Oewiohtskonstani, whereby 20 g (69 %) with a Sohaelpunkt 101 to 10? 0 C.
- 5 109884/1822 - 5 109884/1822
U 974U 974
Daa Infrarotepektrmn 1st identiioh Bit de» von H-a-(p-Chlorbenzoyl)-pHoet&oxyphenyl-hydra*on und atm Kernmagnetieche Reeonansepektpon bestätigt diese Struktur ναού «eigt nur geringe Unreinheiten an»Daa infrared spectrum is identiioh bit de »of Ha- (p-chlorobenzoyl) -pHoet & oxyphenyl-hydra * on and atm nuclear magnetism Reeonansepektpon confirms this structure ναού « has only slight impurities »
berechnet j C 6O,8Oj H 5,06} N 1,41 ί Gl 9,GB %\ gefunden« C 6θ,8θ; H 5,19! N 1,41| Cl 9,61 ^.calculated j C 60.8Oj H 5.06} N 1.41 ί Eq 9, GB% \ found «C 6θ, 8θ; H 5.19! N 1.41 | Cl 9.61 ^.
- 6 10ii84/H22 - 6 10ii84 / H22
Claims (2)
-N-K-C-R2
C-OCHo-CH-X
-NKCR 2
CO
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US25564263A | 1963-02-01 | 1963-02-01 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1793561A1 true DE1793561A1 (en) | 1972-01-20 |
Family
ID=22969254
Family Applications (16)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19641695492 Pending DE1695492A1 (en) | 1963-02-01 | 1964-01-14 | Process for the preparation of indolyl (3) acetic acid compounds |
| DE19641695485 Pending DE1695485A1 (en) | 1963-02-01 | 1964-01-24 | Process for the preparation of indolyl (3) acetic acids |
| DE19641770116 Pending DE1770116A1 (en) | 1963-02-01 | 1964-01-24 | Substituted indolyl (3) acetaldehydes and process for their preparation |
| DE19641793561 Pending DE1793561A1 (en) | 1963-02-01 | 1964-01-24 | Hydrazone compounds and processes for their preparation |
| DE19641770132 Pending DE1770132A1 (en) | 1963-02-01 | 1964-01-24 | Indole compounds and processes for their preparation |
| DE19641695490 Pending DE1695490A1 (en) | 1963-02-01 | 1964-01-24 | Process for the preparation of indolyl (3) acetic acids |
| DE19641695493 Pending DE1695493A1 (en) | 1963-02-01 | 1964-01-24 | Process for the preparation of indolyl (3) acetic acid compounds |
| DE19641695487 Pending DE1695487A1 (en) | 1963-02-01 | 1964-01-24 | Process for the preparation of indolyl (3) acetic acids |
| DE19641770802 Pending DE1770802A1 (en) | 1963-02-01 | 1964-01-24 | Indolyl (3) acetonitriles and process for their preparation |
| DE19641470059D Pending DE1470059B1 (en) | 1963-02-01 | 1964-01-24 | Process for the preparation of substituted indolyl (3) acetic acid compounds and their salts |
| DE19641695486 Pending DE1695486A1 (en) | 1963-02-01 | 1964-01-24 | Process for the preparation of indolyl (3) acetic acid alkyl esters |
| DE19641695488 Pending DE1695488A1 (en) | 1963-02-01 | 1964-01-24 | Process for the preparation of indolyl (3) acetic acids |
| DE19641695484 Pending DE1695484A1 (en) | 1963-02-01 | 1964-01-24 | Process for the preparation of indolyl (3) acetic acid compounds |
| DE19641695489 Pending DE1695489A1 (en) | 1963-02-01 | 1964-01-24 | Process for the preparation of indolyl (3) acetic acid alkyl esters |
| DE19641770134 Pending DE1770134A1 (en) | 1963-02-01 | 1964-01-24 | ss- [indolyl (3)] ethanols and process for their preparation |
| DE19641695491 Pending DE1695491A1 (en) | 1963-02-01 | 1964-01-24 | Process for the preparation of [1-p-chlorobenzoyl-2-methyl-5-methoxyindolyl- (3)] acetic acid and its salts |
Family Applications Before (3)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19641695492 Pending DE1695492A1 (en) | 1963-02-01 | 1964-01-14 | Process for the preparation of indolyl (3) acetic acid compounds |
| DE19641695485 Pending DE1695485A1 (en) | 1963-02-01 | 1964-01-24 | Process for the preparation of indolyl (3) acetic acids |
| DE19641770116 Pending DE1770116A1 (en) | 1963-02-01 | 1964-01-24 | Substituted indolyl (3) acetaldehydes and process for their preparation |
Family Applications After (12)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19641770132 Pending DE1770132A1 (en) | 1963-02-01 | 1964-01-24 | Indole compounds and processes for their preparation |
| DE19641695490 Pending DE1695490A1 (en) | 1963-02-01 | 1964-01-24 | Process for the preparation of indolyl (3) acetic acids |
| DE19641695493 Pending DE1695493A1 (en) | 1963-02-01 | 1964-01-24 | Process for the preparation of indolyl (3) acetic acid compounds |
| DE19641695487 Pending DE1695487A1 (en) | 1963-02-01 | 1964-01-24 | Process for the preparation of indolyl (3) acetic acids |
| DE19641770802 Pending DE1770802A1 (en) | 1963-02-01 | 1964-01-24 | Indolyl (3) acetonitriles and process for their preparation |
| DE19641470059D Pending DE1470059B1 (en) | 1963-02-01 | 1964-01-24 | Process for the preparation of substituted indolyl (3) acetic acid compounds and their salts |
| DE19641695486 Pending DE1695486A1 (en) | 1963-02-01 | 1964-01-24 | Process for the preparation of indolyl (3) acetic acid alkyl esters |
| DE19641695488 Pending DE1695488A1 (en) | 1963-02-01 | 1964-01-24 | Process for the preparation of indolyl (3) acetic acids |
| DE19641695484 Pending DE1695484A1 (en) | 1963-02-01 | 1964-01-24 | Process for the preparation of indolyl (3) acetic acid compounds |
| DE19641695489 Pending DE1695489A1 (en) | 1963-02-01 | 1964-01-24 | Process for the preparation of indolyl (3) acetic acid alkyl esters |
| DE19641770134 Pending DE1770134A1 (en) | 1963-02-01 | 1964-01-24 | ss- [indolyl (3)] ethanols and process for their preparation |
| DE19641695491 Pending DE1695491A1 (en) | 1963-02-01 | 1964-01-24 | Process for the preparation of [1-p-chlorobenzoyl-2-methyl-5-methoxyindolyl- (3)] acetic acid and its salts |
Country Status (11)
| Country | Link |
|---|---|
| AT (1) | AT277992B (en) |
| BE (1) | BE643268A (en) |
| BR (1) | BR6456479D0 (en) |
| CH (16) | CH457435A (en) |
| DE (16) | DE1695492A1 (en) |
| DK (11) | DK109562C (en) |
| FI (9) | FI46955C (en) |
| FR (1) | FR1559559A (en) |
| GB (13) | GB1050739A (en) |
| NL (1) | NL6400813A (en) |
| SE (12) | SE302463B (en) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| HU163233B (en) * | 1970-07-31 | 1973-07-28 | ||
| EP0347776B2 (en) * | 1988-06-21 | 2002-07-10 | Vita Zahnfabrik H. Rauter GmbH & Co. KG | Dispersed ceramic material |
| GB9518994D0 (en) * | 1995-09-16 | 1995-11-15 | Agrevo Uk Ltd | Fungicides |
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- GB GB1050728D patent/GB1050728A/en active Active
- GB GB1050734D patent/GB1050734A/en active Active
- GB GB1050736D patent/GB1050736A/en active Active
- GB GB1050732D patent/GB1050732A/en active Active
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- GB GB1050733D patent/GB1050733A/en active Active
- GB GB1050731D patent/GB1050731A/en active Active
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- GB GB1050738D patent/GB1050738A/en active Active
- GB GB1050739D patent/GB1050739A/en active Active
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1964
- 1964-01-14 DE DE19641695492 patent/DE1695492A1/en active Pending
- 1964-01-24 DE DE19641695485 patent/DE1695485A1/en active Pending
- 1964-01-24 DE DE19641770116 patent/DE1770116A1/en active Pending
- 1964-01-24 DE DE19641793561 patent/DE1793561A1/en active Pending
- 1964-01-24 DE DE19641770132 patent/DE1770132A1/en active Pending
- 1964-01-24 DE DE19641695490 patent/DE1695490A1/en active Pending
- 1964-01-24 DE DE19641695493 patent/DE1695493A1/en active Pending
- 1964-01-24 DE DE19641695487 patent/DE1695487A1/en active Pending
- 1964-01-24 DE DE19641770802 patent/DE1770802A1/en active Pending
- 1964-01-24 DE DE19641470059D patent/DE1470059B1/en active Pending
- 1964-01-24 DE DE19641695486 patent/DE1695486A1/en active Pending
- 1964-01-24 DE DE19641695488 patent/DE1695488A1/en active Pending
- 1964-01-24 DE DE19641695484 patent/DE1695484A1/en active Pending
- 1964-01-24 DE DE19641695489 patent/DE1695489A1/en active Pending
- 1964-01-24 DE DE19641770134 patent/DE1770134A1/en active Pending
- 1964-01-24 DE DE19641695491 patent/DE1695491A1/en active Pending
- 1964-01-28 AT AT01821/67A patent/AT277992B/en not_active IP Right Cessation
- 1964-01-28 BR BR15647964A patent/BR6456479D0/en unknown
- 1964-01-29 FI FI16964A patent/FI46955C/en active
- 1964-01-31 SE SE89267A patent/SE302463B/xx unknown
- 1964-01-31 DK DK598265A patent/DK109562C/en active
- 1964-01-31 CH CH236068A patent/CH457435A/en unknown
- 1964-01-31 DK DK598765A patent/DK109334C/en active
- 1964-01-31 CH CH236268A patent/CH557815A/en not_active IP Right Cessation
- 1964-01-31 CH CH1674768A patent/CH466290A/en unknown
- 1964-01-31 CH CH444166A patent/CH466285A/en unknown
- 1964-01-31 SE SE123764A patent/SE307948B/xx unknown
- 1964-01-31 CH CH1674468A patent/CH466288A/en unknown
- 1964-01-31 CH CH236368A patent/CH457436A/en unknown
- 1964-01-31 SE SE88967A patent/SE317975B/xx unknown
- 1964-01-31 DK DK48964A patent/DK112238B/en unknown
- 1964-01-31 NL NL6400813A patent/NL6400813A/xx unknown
- 1964-01-31 FR FR1559559D patent/FR1559559A/fr not_active Expired
- 1964-01-31 CH CH236568A patent/CH464203A/en unknown
- 1964-01-31 CH CH236668A patent/CH457437A/en unknown
- 1964-01-31 CH CH235868A patent/CH457434A/en unknown
- 1964-01-31 CH CH1674568A patent/CH466289A/en unknown
- 1964-01-31 CH CH236468A patent/CH466283A/en unknown
- 1964-01-31 CH CH236168A patent/CH464202A/en unknown
- 1964-01-31 CH CH490368A patent/CH466287A/en unknown
- 1964-01-31 DK DK598565A patent/DK109514C/en active
- 1964-01-31 BE BE643268D patent/BE643268A/xx unknown
- 1964-01-31 CH CH419468A patent/CH466284A/en unknown
- 1964-01-31 CH CH490268A patent/CH466286A/en unknown
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1965
- 1965-11-22 DK DK598365A patent/DK113501B/en unknown
- 1965-11-22 DK DK598965A patent/DK112314B/en unknown
- 1965-11-22 DK DK598465A patent/DK111751B/en unknown
- 1965-11-22 DK DK598665A patent/DK112239B/en unknown
- 1965-11-22 DK DK598865A patent/DK112313B/en unknown
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1966
- 1966-02-23 DK DK93366A patent/DK112447B/en unknown
- 1966-02-23 DK DK93266A patent/DK112446B/en unknown
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1967
- 1967-01-20 SE SE896/67A patent/SE320666B/xx unknown
- 1967-01-20 SE SE88867A patent/SE302132B/en unknown
- 1967-01-20 SE SE894/67A patent/SE320367B/xx unknown
- 1967-01-20 SE SE891/67A patent/SE304995B/xx unknown
- 1967-01-20 SE SE89367A patent/SE302133B/en unknown
- 1967-01-20 SE SE895/67A patent/SE320069B/xx unknown
- 1967-01-20 SE SE88667A patent/SE302130B/en unknown
- 1967-01-20 SE SE890/67A patent/SE307133B/xx unknown
- 1967-01-31 SE SE88767A patent/SE302131B/xx unknown
- 1967-02-23 CH CH115364A patent/CH489495A/en not_active IP Right Cessation
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1970
- 1970-09-21 FI FI257070A patent/FI47097B/fi active
- 1970-09-21 FI FI702570A patent/FI47097C/en active
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- 1970-09-21 FI FI256870A patent/FI47096C/en active
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- 1970-09-21 FI FI257170A patent/FI47098C/en active
- 1970-09-21 FI FI257570A patent/FI47101C/en active
- 1970-09-21 FI FI257370A patent/FI47185C/en active
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