NO127186B - - Google Patents
Download PDFInfo
- Publication number
- NO127186B NO127186B NO149770A NO149770A NO127186B NO 127186 B NO127186 B NO 127186B NO 149770 A NO149770 A NO 149770A NO 149770 A NO149770 A NO 149770A NO 127186 B NO127186 B NO 127186B
- Authority
- NO
- Norway
- Prior art keywords
- piperidyl
- methyl
- pyrazolone
- ynyl
- prop
- Prior art date
Links
- OAKJQQAXSVQMHS-UHFFFAOYSA-N hydrazine Substances NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims description 9
- JEXVQSWXXUJEMA-UHFFFAOYSA-N pyrazol-3-one Chemical class O=C1C=CN=N1 JEXVQSWXXUJEMA-UHFFFAOYSA-N 0.000 claims description 9
- 229940083761 high-ceiling diuretics pyrazolone derivative Drugs 0.000 claims description 3
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 125000000304 alkynyl group Chemical group 0.000 claims description 2
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 2
- 125000003118 aryl group Chemical group 0.000 claims description 2
- 125000000068 chlorophenyl group Chemical group 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
- 238000000034 method Methods 0.000 claims description 2
- 125000003944 tolyl group Chemical group 0.000 claims description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 26
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 14
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- 238000006243 chemical reaction Methods 0.000 description 6
- 238000010438 heat treatment Methods 0.000 description 5
- 238000006418 Brown reaction Methods 0.000 description 4
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 4
- 238000001816 cooling Methods 0.000 description 4
- 238000001953 recrystallisation Methods 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 238000002425 crystallisation Methods 0.000 description 2
- 230000008025 crystallization Effects 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- XTEGVFVZDVNBPF-UHFFFAOYSA-N naphthalene-1,5-disulfonic acid Chemical compound C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1S(O)(=O)=O XTEGVFVZDVNBPF-UHFFFAOYSA-N 0.000 description 2
- HXUIDZOMTRMIOE-UHFFFAOYSA-N 3-oxo-3-phenylpropionic acid Chemical compound OC(=O)CC(=O)C1=CC=CC=C1 HXUIDZOMTRMIOE-UHFFFAOYSA-N 0.000 description 1
- -1 chlor- Chemical class 0.000 description 1
- LXCDLPDPVLFZGQ-UHFFFAOYSA-N ethyl 2-benzoylpent-4-ynoate Chemical compound CCOC(=O)C(CC#C)C(=O)C1=CC=CC=C1 LXCDLPDPVLFZGQ-UHFFFAOYSA-N 0.000 description 1
- KSTSKHKQRFGSJH-UHFFFAOYSA-N ethyl 2-benzyl-3-oxo-3-phenylpropanoate Chemical compound C=1C=CC=CC=1C(=O)C(C(=O)OCC)CC1=CC=CC=C1 KSTSKHKQRFGSJH-UHFFFAOYSA-N 0.000 description 1
- 125000004494 ethyl ester group Chemical group 0.000 description 1
- 150000004702 methyl esters Chemical class 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C04—CEMENTS; CONCRETE; ARTIFICIAL STONE; CERAMICS; REFRACTORIES
- C04B—LIME, MAGNESIA; SLAG; CEMENTS; COMPOSITIONS THEREOF, e.g. MORTARS, CONCRETE OR LIKE BUILDING MATERIALS; ARTIFICIAL STONE; CERAMICS; REFRACTORIES; TREATMENT OF NATURAL STONE
- C04B35/00—Shaped ceramic products characterised by their composition; Ceramics compositions; Processing powders of inorganic compounds preparatory to the manufacturing of ceramic products
- C04B35/515—Shaped ceramic products characterised by their composition; Ceramics compositions; Processing powders of inorganic compounds preparatory to the manufacturing of ceramic products based on non-oxide ceramics
- C04B35/52—Shaped ceramic products characterised by their composition; Ceramics compositions; Processing powders of inorganic compounds preparatory to the manufacturing of ceramic products based on non-oxide ceramics based on carbon, e.g. graphite
- C04B35/528—Shaped ceramic products characterised by their composition; Ceramics compositions; Processing powders of inorganic compounds preparatory to the manufacturing of ceramic products based on non-oxide ceramics based on carbon, e.g. graphite obtained from carbonaceous particles with or without other non-organic components
- C04B35/532—Shaped ceramic products characterised by their composition; Ceramics compositions; Processing powders of inorganic compounds preparatory to the manufacturing of ceramic products based on non-oxide ceramics based on carbon, e.g. graphite obtained from carbonaceous particles with or without other non-organic components containing a carbonisable binder
-
- C—CHEMISTRY; METALLURGY
- C21—METALLURGY OF IRON
- C21B—MANUFACTURE OF IRON OR STEEL
- C21B7/00—Blast furnaces
- C21B7/04—Blast furnaces with special refractories
- C21B7/06—Linings for furnaces
Landscapes
- Engineering & Computer Science (AREA)
- Chemical & Material Sciences (AREA)
- Manufacturing & Machinery (AREA)
- Ceramic Engineering (AREA)
- Materials Engineering (AREA)
- Organic Chemistry (AREA)
- Structural Engineering (AREA)
- Metallurgy (AREA)
- Ceramic Products (AREA)
- Furnace Housings, Linings, Walls, And Ceilings (AREA)
- Plural Heterocyclic Compounds (AREA)
- Hydrogenated Pyridines (AREA)
Description
Fremgangsmåte for fremstilling av pyrazolon-derivater. Process for the preparation of pyrazolone derivatives.
Det har vist seg at det kan oppnås nye It has been shown that new ones can be achieved
pyrazolonderivater med den alminnelige formel: pyrazolone derivatives of the general formula:
hvor R1 betyr et lavere alkyl, R2 er aryl, klorfenyl eller tolyl og R3 en aralkyl- eller alkynyl-rest, ved at et N-alkyl-piperidyl-4-hydrazin med den alminnelige formel: hvor Rj har samme betydning som ovenfor, omsettes på i og for seg kjent måte med (3-ketosyrer eller deres reaksjonsdyk-tige derivater med den alminnelige formel: where R1 means a lower alkyl, R2 is aryl, chlorophenyl or tolyl and R3 an aralkyl or alkynyl residue, by reacting an N-alkyl-piperidyl-4-hydrazine with the general formula: where Rj has the same meaning as above in a manner known per se with (3-keto acids or their reactive derivatives with the general formula:
hvor R2 og R3 har samme betydning where R2 and R3 have the same meaning
som ovenfor og X står for hydroksyl eller en O-alkylgruppe. as above and X stands for hydroxyl or an O-alkyl group.
Eksempel 1. Example 1.
1- (N-metyl-piperidyl-4') -3-f enyl-4-(prop-2-ynyl)-pyrazolon-5. 6,7 g N-metyl-piperidyl-4-hydrazin og 11,9 g a-(prop-2-ynyl)-benzoyl-eddiksyre-etylester fikk stå 1 y2 time ved romtemperatur. Deretter ble 1-(N-methyl-piperidyl-4')-3-phenyl-4-(prop-2-ynyl)-pyrazolone-5. 6.7 g of N-methyl-piperidyl-4-hydrazine and 11.9 g of α-(prop-2-ynyl)-benzoyl-acetic acid ethyl ester were allowed to stand for 1 and 2 hours at room temperature. Then became
det foretatt oppvarmning i 1 time til 80°, 2 timer til 110°, og deretter fikk blandingen stå i ennu i/2 time ved denne temperatur i vakuum ved 12 mm Hg. Den hårde, mørkebrune reaksjonsblanding ble deretter oppløst i varm etanol, hvorunder 1-(N-metyl-piperidyl-4')-3-fenyl-4-(prop-2-ynyl)-pyrazolon-5 skilte seg ut krystallinsk ved avkjøling. Etter to gangers omkrystallisering fra etanol smeltet pyrazo-londerivatet ved 134—136° (sp). heating was carried out for 1 hour at 80°, 2 hours at 110°, and then the mixture was allowed to stand for another 1/2 hour at this temperature in a vacuum at 12 mm Hg. The hard, dark brown reaction mixture was then dissolved in hot ethanol, during which 1-(N-methyl-piperidyl-4')-3-phenyl-4-(prop-2-ynyl)-pyrazolone-5 crystallized out on cooling. After recrystallization from ethanol twice, the pyrazolone derivative melted at 134-136° (sp).
Ved å blande en metanoloppløsning av basen med den beregnete mengdé naftalin-1,5-disulfonsyre ble det oppnådd 1-(N-metyl-piperidyl-4') -3-f enyl-4- (prop-2-ynyl) - pyrazolon-5-naftalin-l,5-disulfonat . 2H20 By mixing a methanol solution of the base with the calculated amount of naphthalene-1,5-disulfonic acid, 1-(N-methyl-piperidyl-4')-3-phenyl-4-(prop-2-ynyl)-pyrazolone was obtained -5-naphthalene-1,5-disulfonate . 2H20
(mol.vekt 915,1). Smp. 180° (sp) fra meta-nol. (mol. weight 915.1). Temp. 180° (sp) from methanol.
Til en metanoloppløsning av 1- (N-metyl-piperidyl-4') -3-fenyl-4-(prop-2-ynyl)-pyrazolon-5 ble det satt en metanoloppløs-ning av den ekvivalente mengde oksalsyre. Oppløsningen ble fortettet til et lite vo-lum og fikk stå noen dager hvorved det nøytrale oksalat ble oppnådd i krystallinsk tilstand. Smp. 140° (sp). To a methanol solution of 1-(N-methyl-piperidyl-4')-3-phenyl-4-(prop-2-ynyl)-pyrazolone-5 was added a methanol solution of the equivalent amount of oxalic acid. The solution was concentrated to a small volume and allowed to stand for a few days, whereby the neutral oxalate was obtained in a crystalline state. Temp. 140° (sp).
Eksempel 2. Example 2.
1-(N-metyl-piperidyl-4')-3-f enyl-4-benzyl-pyrazolon-5. 5,6 g a-benzyl-ben-zoyl-eddiksyre-etylester og 2,6 g N-metyl-piperidyl-4-hydrazin ble oppvarmet i en time til 80°, en time til 110° og tre timer til 130°, hvorunder reaksjonsproduktet, 1-(N-metyl-piperidyl-4')-3-fenyl-4-benzyl- 1-(N-methyl-piperidyl-4')-3-phenyl-4-benzyl-pyrazolone-5. 5.6 g of α-benzyl-benzoyl-acetic acid ethyl ester and 2.6 g of N-methyl-piperidyl-4-hydrazine were heated for one hour at 80°, one hour at 110° and three hours at 130°, wherein the reaction product, 1-(N-methyl-piperidyl-4')-3-phenyl-4-benzyl-
pyrazolon-5 begynte å skille seg ut krystal- pyrazolone-5 began to separate cryst-
linsk. For å avslutte reaksjonen og for full- linsk. To terminate the reaction and for complete-
stendig å fjerne den etanol som var dannet, constantly removing the ethanol that had formed,
ble det deretter foretatt oppvarmning i ytterligere y2 time ved 12 mm Hg til 120°. heating was then carried out for an additional y2 hours at 12 mm Hg to 120°.
Etter avkjøling ble reaksjonsmassen revet After cooling, the reaction mass was shredded
med eter, filtrert og pyrazolon-derivatet omkrystallisert fra etanol. Smp. 181—183° with ether, filtered and the pyrazolone derivative recrystallized from ethanol. Temp. 181—183°
(sp) fra etanol. (sp) from ethanol.
Eksempel 3. Example 3.
1 - (N-metyl-piperidyl-4') -3-f enyl-4-(prop-2-ynyl)-pyrazolon-5. 4,0 g a-(prop-2-ynyl)benzoyl-eddiksyre i 8 cm3 abs klo- 1-(N-methyl-piperidyl-4')-3-phenyl-4-(prop-2-ynyl)-pyrazolone-5. 4.0 g of a-(prop-2-ynyl)benzoyl-acetic acid in 8 cm3 abs chlor-
roform ble blandet med 2,6 g N-metyl-piperidyl-4-hydrazin ved romtemperatur, og blandingen ble oppvarmet i løpet av 30 roform was mixed with 2.6 g of N-methyl-piperidyl-4-hydrazine at room temperature, and the mixture was heated for 30
min. til 80°. Deretter ble reaksj onsblandin- my. to 80°. Then, the reaction mixture was
gen oppvarmet videre i to timer til 110°, again heated for two hours to 110°,
og deretter holdt i ennu 30 min i vakuum (12 mm Hg) på denne temperatur. Den hårde, mørkebrune reaksjonsmasse ble der- and then held for another 30 min in vacuum (12 mm Hg) at this temperature. The hard, dark brown reaction mass was then
etter oppløst i varm etanol og langsomt avkjølet, hvorunder l-(N-metyl-piperidyl-4') -3-f enyl-4- (prop-2-ynyl)pyrazolon-5 after dissolved in hot ethanol and slowly cooled, during which 1-(N-methyl-piperidyl-4')-3-phenyl-4-(prop-2-ynyl)pyrazolone-5
skilte seg ut krystallinsk. Etter ytterligere omkrystallisering fra etanol smeltet pyrazolon-derivatet ved 134—136° (sp). stood out crystalline. After further recrystallization from ethanol, the pyrazolone derivative melted at 134-136° (sp).
Eksempel 4. Example 4.
1-(N-metyl-piperidyl-4')-3-f enyl-4-benzyl-pyrazolon-5. 2,5 g a-benzyl-benzo-yleddiksyre i 4 cm3 abs kloroform og 1,3 g N-metyl-piperidyl-4-hydrazin ble oppvar- 1-(N-methyl-piperidyl-4')-3-phenyl-4-benzyl-pyrazolone-5. 2.5 g of α-benzyl-benzo-ylacetic acid in 4 cm3 abs chloroform and 1.3 g of N-methyl-piperidyl-4-hydrazine were heated
met i en åpen reaksjonskolbe i løpet av 30 met in an open reaction flask during 30
min til 110°, så i 3 timer til 130° og derpå min to 110°, then for 3 hours to 130° and then
holdt i 30 min. i vakuum ved 12 mm Hg på denne temperatur. Etter avkjøling ble reaksjonsmassen revet med eter, filtrert og 1- (N-metyl-piperidyl-4') -3-f enyl-4-ben-zyl-pyrazolon-5 omkrystallisert fra etanol. held for 30 min. in vacuum at 12 mm Hg at this temperature. After cooling, the reaction mass was triturated with ether, filtered and 1-(N-methyl-piperidyl-4')-3-phenyl-4-benzyl-pyrazolone-5 recrystallized from ethanol.
Smp. 181—183° (sp) fra etanol. Temp. 181-183° (mp) from ethanol.
Eksempel 5. Example 5.
1-(N-metyl-piperidyl-4')-3-f enyl-4-benzyl-pyrazolon-5. 2,7 g a-benzyl-benzo- 1-(N-methyl-piperidyl-4')-3-phenyl-4-benzyl-pyrazolone-5. 2.7 g of a-benzyl-benzo-
yleddiksyre-metylester og 1,3 g N-metyl-piperidyl-4-hydrazin ble oppvarmet i 2 ti- ylacetic acid methyl ester and 1.3 g of N-methyl-piperidyl-4-hydrazine were heated for 2 ti-
mer til 100° og i 3 timer til 135°, hvorunder reaksj onsproduktet, 1 - (N-metyl-piperidyl-4')-3-fenyl-4-benzyl-pyrazolon-5 begynte å skille seg ut krystallinsk. For å avslutte reaksjonen og for fullstendig å fjerne den etanol som var dannet ble det foretatt oppvarmning i ennu 30 min. i vakuum (12 more to 100° and for 3 hours to 135°, during which the reaction product, 1 - (N-methyl-piperidyl-4')-3-phenyl-4-benzyl-pyrazolone-5 began to separate out crystalline. To terminate the reaction and to completely remove the ethanol that had formed, heating was carried out for another 30 min. in vacuum (12
mm Hg) til 125°. Etter avkjøling ble reaksjonsmassen revet med eter, filtrert og pyrazolon-derivatet omkrystallisert fra eta- mm Hg) to 125°. After cooling, the reaction mass was triturated with ether, filtered and the pyrazolone derivative recrystallized from ether
nol. Smp. 181—183° (sp) fra etanol. nil Temp. 181-183° (mp) from ethanol.
Eksempel 6. Example 6.
1-(N-metyl-piperidyl-4')-3-(p-klorfenyl)-4-(prop-2-ynyl)-pyrazolon-5. 2,6 g N-metyl-piperidyl-4-hydrazin og 5,3 g a-(prop-2-ynyl)-(p-klor-benzoyl)-eddik- 1-(N-methyl-piperidyl-4')-3-(p-chlorophenyl)-4-(prop-2-ynyl)-pyrazolone-5. 2.6 g of N-methyl-piperidyl-4-hydrazine and 5.3 g of α-(prop-2-ynyl)-(p-chloro-benzoyl)-acetic
syreetylester ble blandet og fikk stå i y2acid ethyl ester was mixed and allowed to stand in y2
time ved romtemperatur. Deretter ble det foretatt oppvarmning i en time til 80°, 3 hour at room temperature. Heating was then carried out for one hour to 80°, 3
timer til 100° og tilslutt i ennu y2 time til 110° i vakuum ved 12 mm Hg. Den mørke- hours to 100° and finally for another y2 hours to 110° in vacuum at 12 mm Hg. The dark-
brune reaksj onsblanding ble så revet med eter, og filtrert, og filterresten, pyrazolon-derivatet, ble brakt til krystallisering fra etanol. Etter to gangers omkrystallisering fra etanol smeltet l-(N-metyl-piperidyl-4')-3-(p-klorfenyl)-4-(prop-2-ynyl)-py- brown reaction mixture was then triturated with ether, and filtered, and the filter residue, the pyrazolone derivative, was brought to crystallization from ethanol. After recrystallization twice from ethanol, 1-(N-methyl-piperidyl-4')-3-(p-chlorophenyl)-4-(prop-2-ynyl)-py-
razolon-5 ved 265—267° (sp). razolon-5 at 265—267° (sp).
Eksempel 7. Example 7.
1-(N-metyl-piperidyl-4')-3-(p-tolyl)-4-(prop-2-ynyl)-pyrazolon-5. 2,6 g N-metyl-piperidyl-4-hy drazin og 4,9 g a-(prop-2-ynyl)-(p-toluen)-eddiksyreetylester ble blandet og fikk stå i y2 time ved romtem- 1-(N-methyl-piperidyl-4')-3-(p-tolyl)-4-(prop-2-ynyl)-pyrazolone-5. 2.6 g of N-methyl-piperidyl-4-hydrazine and 4.9 g of α-(prop-2-ynyl)-(p-toluene)-acetic acid ethyl ester were mixed and allowed to stand for y2 hours at room temperature
peratur. Deretter ble det foretatt oppvarm- perature. Afterwards, heating was carried out
ning i 1 time til 80°, 3 timer til 100° og til- ning for 1 hour at 80°, 3 hours at 100° and
slutt i ennu y2 time til 110° i vakuum ved 12 mm Hg. Den mørkebrune reaksj onsblan- finally for another y2 hours at 110° in vacuum at 12 mm Hg. The dark brown reaction mix-
ding ble deretter revet med eter og filt- ding was then torn with ether and felt-
rert, og filterresten, pyrazolon-derivatet, rert, and the filter residue, the pyrazolone derivative,
ble brakt til krystallisering fra benzol/pe- was brought to crystallization from benzene/pe-
troleter. Ette 2 gangers omkrystallisering fra benzol-petroleter smeltet 1-(N-metyl-piperidyl-4) -3- (p-tolyl) -4- (prop-2-ynyl) - pyrazolon-5 ved 131—134° (sp). trolleys. One 2 times recrystallization from benzene-petroleum ether melted 1-(N-methyl-piperidyl-4)-3-(p-tolyl)-4-(prop-2-ynyl)-pyrazolone-5 at 131—134° (sp) .
Claims (1)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19691931395 DE1931395B2 (en) | 1969-06-20 | 1969-06-20 | Use of semi-graphite bricks to line the rest of the blast furnace |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NO127186B true NO127186B (en) | 1973-05-21 |
Family
ID=5737572
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO149770A NO127186B (en) | 1969-06-20 | 1970-04-20 |
Country Status (9)
| Country | Link |
|---|---|
| AT (1) | AT299282B (en) |
| BE (1) | BE752241A (en) |
| DE (1) | DE1931395B2 (en) |
| ES (1) | ES380418A1 (en) |
| FR (1) | FR2048421A5 (en) |
| GB (1) | GB1294491A (en) |
| NL (1) | NL150410B (en) |
| NO (1) | NO127186B (en) |
| SE (1) | SE376016B (en) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE102017124358B4 (en) * | 2017-10-18 | 2019-08-01 | Refratechnik Holding Gmbh | Use of an offset and / or a shaped or unshaped refractory product for refractory lining of a coal gasification plant, such delivery and coal gasification plant with such delivery |
-
1969
- 1969-06-20 DE DE19691931395 patent/DE1931395B2/en active Pending
-
1970
- 1970-03-17 NL NL7003782A patent/NL150410B/en not_active IP Right Cessation
- 1970-04-13 AT AT336370A patent/AT299282B/en not_active IP Right Cessation
- 1970-04-20 NO NO149770A patent/NO127186B/no unknown
- 1970-05-04 ES ES380418A patent/ES380418A1/en not_active Expired
- 1970-05-12 FR FR7017262A patent/FR2048421A5/fr not_active Expired
- 1970-06-12 GB GB2869170A patent/GB1294491A/en not_active Expired
- 1970-06-18 SE SE845270A patent/SE376016B/xx unknown
- 1970-06-19 BE BE752241D patent/BE752241A/en not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| AT299282B (en) | 1972-06-12 |
| ES380418A1 (en) | 1972-09-01 |
| FR2048421A5 (en) | 1971-03-19 |
| BE752241A (en) | 1970-12-21 |
| SE376016B (en) | 1975-05-05 |
| NL7003782A (en) | 1970-12-22 |
| GB1294491A (en) | 1972-10-25 |
| DE1931395B2 (en) | 1973-09-27 |
| NL150410B (en) | 1976-08-16 |
| DE1931395A1 (en) | 1970-12-23 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US2642438A (en) | Pyridindoles and method of manufacture | |
| US2773875A (en) | Indole derivatives and method for producing same | |
| NO752493L (en) | ||
| US2704757A (en) | 5-hydroxy-3, 4, 5, 6-tetrahydropyriminines | |
| NO127186B (en) | ||
| US3158609A (en) | Diphenylmethyl-1-aminopiperidine hydrazones and congeners | |
| US2512732A (en) | Carbamic acid esters of (3-hydroxy-2-pyridylmethyl) amines and salts thereof | |
| CH472407A (en) | Process for the preparation of new 2-benzyl-1,3,4,9b-tetrahydro-2H-indeno (1,2-c) pyridine derivatives | |
| NO156978B (en) | TRIBUTYLPHENOL ETERSULPHONATES AND THEIR USE. | |
| US2546159A (en) | Piperidyl ketones and process of | |
| US2626948A (en) | 1-alkyl-2 or 4-[(n-alkyl-n-beta-dialkyl-aminoalkyl) aminophenethyl]-piperidines and salts thereof | |
| US2951080A (en) | Novel phenyl-substituted piperidines | |
| US3056786A (en) | C-substituted piperazine derivatives and method | |
| US2970147A (en) | 3-hydroxy-nu-(heterocyclic-ethyl)-morphinans | |
| US2742475A (en) | Azacycloalkanes | |
| US2749346A (en) | Tetrahydropyridine compounds | |
| US2456785A (en) | Production of amides | |
| US2517695A (en) | Production of 1-alkyl 4-phenylpiperidyl 4-ketones | |
| US2762805A (en) | 3-ethyl-3-phenyl-2, 6-piperazinedione and derivatives thereof | |
| NO115462B (en) | ||
| US2537854A (en) | Tetrahydropyridines and method of manufacture | |
| US2953598A (en) | Acyl hydrazines | |
| US3217009A (en) | 1-(3-oximino-3-phenylpropyl)-4-phenyl-4-propionoxy-piperidine | |
| US3290316A (en) | Alpha-3-pyridylmandelic acid and derivatives thereof | |
| US3093651A (en) | Nu-alkyl-2-(2-[9-carbazolyl-ethyl])-piperidines |