NO126625B - - Google Patents

Download PDF

Info

Publication number: NO126625B
Authority: NO; Norway
Prior art keywords: hydride; formula; general formula; sodium; compound
Prior art date: 1968-11-18

Application number

NO04554/69A

Other languages

English (en)

Norwegian (no)

Inventor

George Francis Field

Leo Henryk Sternbach

Original Assignee

Hoffmann La Roche

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.)

1968-11-18

Filing date

1969-11-17

Publication date

1973-03-05

1969-11-17 Application filed by Hoffmann La Roche filed Critical Hoffmann La Roche

1973-03-05 Publication of NO126625B publication Critical patent/NO126625B/no

Links

-1 lithium aluminum hydride Chemical compound 0.000 claims description 28
150000001875 compounds Chemical class 0.000 claims description 22
239000012280 lithium aluminium hydride Substances 0.000 claims description 10
239000001257 hydrogen Substances 0.000 claims description 8
229910052739 hydrogen Inorganic materials 0.000 claims description 8
125000004423 acyloxy group Chemical group 0.000 claims description 7
238000000034 method Methods 0.000 claims description 7
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 5
125000003545 alkoxy group Chemical group 0.000 claims description 5
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
SIPUZPBQZHNSDW-UHFFFAOYSA-N bis(2-methylpropyl)aluminum Chemical compound CC(C)C[Al]CC(C)C SIPUZPBQZHNSDW-UHFFFAOYSA-N 0.000 claims description 3
229910052736 halogen Inorganic materials 0.000 claims description 3
150000002367 halogens Chemical class 0.000 claims description 3
229910052987 metal hydride Inorganic materials 0.000 claims description 3
150000004681 metal hydrides Chemical class 0.000 claims description 3
238000002360 preparation method Methods 0.000 claims description 3
239000003638 chemical reducing agent Substances 0.000 claims description 2
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 21
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 18
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 16
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 15
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 12
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 11
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 9
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 9
238000006243 chemical reaction Methods 0.000 description 8
239000000203 mixture Substances 0.000 description 8
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 7
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
239000002244 precipitate Substances 0.000 description 6
239000003513 alkali Substances 0.000 description 5
150000002430 hydrocarbons Chemical class 0.000 description 5
239000000155 melt Substances 0.000 description 5
229910052938 sodium sulfate Inorganic materials 0.000 description 5
235000011152 sodium sulphate Nutrition 0.000 description 5
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 4
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
239000002585 base Substances 0.000 description 4
229930195733 hydrocarbon Natural products 0.000 description 4
238000001953 recrystallisation Methods 0.000 description 4
229910052708 sodium Inorganic materials 0.000 description 4
239000011734 sodium Substances 0.000 description 4
239000012312 sodium hydride Substances 0.000 description 4
229910000104 sodium hydride Inorganic materials 0.000 description 4
239000002904 solvent Substances 0.000 description 4
239000007858 starting material Substances 0.000 description 4
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 3
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
229910052783 alkali metal Inorganic materials 0.000 description 3
150000001340 alkali metals Chemical group 0.000 description 3
125000004432 carbon atom Chemical group C* 0.000 description 3
238000000354 decomposition reaction Methods 0.000 description 3
230000018044 dehydration Effects 0.000 description 3
238000006297 dehydration reaction Methods 0.000 description 3
239000000706 filtrate Substances 0.000 description 3
150000002431 hydrogen Chemical class 0.000 description 3
239000012442 inert solvent Substances 0.000 description 3
238000002844 melting Methods 0.000 description 3
230000008018 melting Effects 0.000 description 3
MRMWQMZFUWXMLF-UHFFFAOYSA-N 7-chloro-4-hydroxy-5-phenyl-1,2,3,5-tetrahydro-1,4-benzodiazepine Chemical compound ClC=1C=CC2=C(C(N(CCN2)O)C2=CC=CC=C2)C1 MRMWQMZFUWXMLF-UHFFFAOYSA-N 0.000 description 2
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
125000003668 acetyloxy group Chemical group [H]C([H])([H])C(=O)O[*] 0.000 description 2
150000001408 amides Chemical class 0.000 description 2
239000000460 chlorine Substances 0.000 description 2
229910052801 chlorine Inorganic materials 0.000 description 2
239000006185 dispersion Substances 0.000 description 2
150000002170 ethers Chemical class 0.000 description 2
239000000284 extract Substances 0.000 description 2
125000005843 halogen group Chemical group 0.000 description 2
150000004678 hydrides Chemical class 0.000 description 2
238000002329 infrared spectrum Methods 0.000 description 2
INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 2
238000004519 manufacturing process Methods 0.000 description 2
239000002480 mineral oil Substances 0.000 description 2
235000010446 mineral oil Nutrition 0.000 description 2
239000003921 oil Substances 0.000 description 2
239000012074 organic phase Substances 0.000 description 2
239000003960 organic solvent Substances 0.000 description 2
239000011541 reaction mixture Substances 0.000 description 2
235000017557 sodium bicarbonate Nutrition 0.000 description 2
229910000030 sodium bicarbonate Inorganic materials 0.000 description 2
QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 2
WGTYBPLFGIVFAS-UHFFFAOYSA-M tetramethylammonium hydroxide Chemical compound [OH-].C[N+](C)(C)C WGTYBPLFGIVFAS-UHFFFAOYSA-M 0.000 description 2
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
UVGLQEHMAHOVRY-UHFFFAOYSA-N 7-chloro-4-hydroxy-1-methyl-5-phenyl-3,5-dihydro-2H-1,4-benzodiazepine Chemical compound ClC=1C=CC2=C(C(N(CCN2C)O)C2=CC=CC=C2)C1 UVGLQEHMAHOVRY-UHFFFAOYSA-N 0.000 description 1
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
BMTAFVWTTFSTOG-UHFFFAOYSA-N Butylate Chemical group CCSC(=O)N(CC(C)C)CC(C)C BMTAFVWTTFSTOG-UHFFFAOYSA-N 0.000 description 1
XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 1
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
PBDYKLIQMZIDKS-UHFFFAOYSA-N N1=NC=C(CC2=C1C=CC=C2)O Chemical class N1=NC=C(CC2=C1C=CC=C2)O PBDYKLIQMZIDKS-UHFFFAOYSA-N 0.000 description 1
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 1
239000002253 acid Substances 0.000 description 1
150000007513 acids Chemical class 0.000 description 1
150000001298 alcohols Chemical class 0.000 description 1
229910001854 alkali hydroxide Inorganic materials 0.000 description 1
150000008044 alkali metal hydroxides Chemical class 0.000 description 1
150000001447 alkali salts Chemical class 0.000 description 1
229910000095 alkaline earth hydride Inorganic materials 0.000 description 1
150000004703 alkoxides Chemical class 0.000 description 1
125000000217 alkyl group Chemical group 0.000 description 1
239000008346 aqueous phase Substances 0.000 description 1
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 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
AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 description 1
239000000920 calcium hydroxide Substances 0.000 description 1
229910001861 calcium hydroxide Inorganic materials 0.000 description 1
150000001718 carbodiimides Chemical class 0.000 description 1
BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical class OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
238000003776 cleavage reaction Methods 0.000 description 1
239000012024 dehydrating agents‎ Substances 0.000 description 1
VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 description 1
230000008030 elimination Effects 0.000 description 1
238000003379 elimination reaction Methods 0.000 description 1
125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
229910052731 fluorine Inorganic materials 0.000 description 1
239000011737 fluorine Substances 0.000 description 1
150000008282 halocarbons Chemical class 0.000 description 1
XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
150000004679 hydroxides Chemical class 0.000 description 1
125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
150000007529 inorganic bases Chemical class 0.000 description 1
239000000543 intermediate Substances 0.000 description 1
PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
150000002500 ions Chemical class 0.000 description 1
239000012948 isocyanate Substances 0.000 description 1
150000002513 isocyanates Chemical class 0.000 description 1
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
AFRJJFRNGGLMDW-UHFFFAOYSA-N lithium amide Chemical compound [Li+].[NH2-] AFRJJFRNGGLMDW-UHFFFAOYSA-N 0.000 description 1
SIAPCJWMELPYOE-UHFFFAOYSA-N lithium hydride Chemical compound [LiH] SIAPCJWMELPYOE-UHFFFAOYSA-N 0.000 description 1
229910000103 lithium hydride Inorganic materials 0.000 description 1
239000012022 methylating agents‎ Substances 0.000 description 1
230000001035 methylating effect Effects 0.000 description 1
230000011987 methylation Effects 0.000 description 1
238000007069 methylation reaction Methods 0.000 description 1
ZGEGCLOFRBLKSE-UHFFFAOYSA-N methylene hexane Natural products CCCCCC=C ZGEGCLOFRBLKSE-UHFFFAOYSA-N 0.000 description 1
150000007530 organic bases Chemical class 0.000 description 1
239000012044 organic layer Substances 0.000 description 1
DGTNSSLYPYDJGL-UHFFFAOYSA-N phenyl isocyanate Chemical compound O=C=NC1=CC=CC=C1 DGTNSSLYPYDJGL-UHFFFAOYSA-N 0.000 description 1
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
108090000623 proteins and genes Proteins 0.000 description 1
238000007142 ring opening reaction Methods 0.000 description 1
150000003839 salts Chemical class 0.000 description 1
230000007017 scission Effects 0.000 description 1
ODZPKZBBUMBTMG-UHFFFAOYSA-N sodium amide Chemical compound [NH2-].[Na+] ODZPKZBBUMBTMG-UHFFFAOYSA-N 0.000 description 1
239000011780 sodium chloride Substances 0.000 description 1
238000003756 stirring Methods 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D243/00—Heterocyclic compounds containing seven-membered rings having two nitrogen atoms as the only ring hetero atoms
- C07D243/06—Heterocyclic compounds containing seven-membered rings having two nitrogen atoms as the only ring hetero atoms having the nitrogen atoms in positions 1 and 4
- C07D243/10—Heterocyclic compounds containing seven-membered rings having two nitrogen atoms as the only ring hetero atoms having the nitrogen atoms in positions 1 and 4 condensed with carbocyclic rings or ring systems
- C07D243/14—1,4-Benzodiazepines; Hydrogenated 1,4-benzodiazepines
- C07D243/16—1,4-Benzodiazepines; Hydrogenated 1,4-benzodiazepines substituted in position 5 by aryl radicals
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D497/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having oxygen and sulfur atoms as the only ring hetero atoms
- C07D497/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having oxygen and sulfur atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D497/04—Ortho-condensed systems

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Agricultural Chemicals And Associated Chemicals (AREA)
Plural Heterocyclic Compounds (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)

NO04554/69A 1968-11-18 1969-11-17 NO126625B (fi)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
US77677568A	1968-11-18	1968-11-18

Publications (1)

Publication Number	Publication Date
NO126625B true NO126625B (fi)	1973-03-05

Family

ID=25108328

Family Applications (2)

Application Number	Title	Priority Date	Filing Date
NO04554/69A NO126625B (fi)	1968-11-18	1969-11-17
NO03021/71A NO127349B (fi)	1968-11-18	1971-08-12

Family Applications After (1)

Application Number	Title	Priority Date	Filing Date
NO03021/71A NO127349B (fi)	1968-11-18	1971-08-12

Country Status (14)

Country	Link
AT (1)	AT294839B (fi)
BE (1)	BE741765A (fi)
BR (1)	BR6914223D0 (fi)
CH (1)	CH526557A (fi)
DE (1)	DE1957961A1 (fi)
ES (1)	ES373596A1 (fi)
FI (1)	FI50626C (fi)
FR (1)	FR2023553A1 (fi)
GB (1)	GB1233828A (fi)
IL (1)	IL33251A0 (fi)
NL (1)	NL6916954A (fi)
NO (2)	NO126625B (fi)
SE (2)	SE367198B (fi)
YU (1)	YU34206B (fi)

1969
- 1969-10-27 CH CH1597469A patent/CH526557A/de not_active IP Right Cessation
- 1969-10-27 IL IL33251A patent/IL33251A0/xx unknown
- 1969-11-07 FI FI693223A patent/FI50626C/fi active
- 1969-11-11 NL NL6916954A patent/NL6916954A/xx not_active Application Discontinuation
- 1969-11-11 GB GB1233828D patent/GB1233828A/en not_active Expired
- 1969-11-17 BR BR214223/69A patent/BR6914223D0/pt unknown
- 1969-11-17 YU YU2878/69A patent/YU34206B/xx unknown
- 1969-11-17 BE BE741765D patent/BE741765A/xx unknown
- 1969-11-17 ES ES373596A patent/ES373596A1/es not_active Expired
- 1969-11-17 NO NO04554/69A patent/NO126625B/no unknown
- 1969-11-17 AT AT1071469A patent/AT294839B/de not_active IP Right Cessation
- 1969-11-18 SE SE15821/69A patent/SE367198B/xx unknown
- 1969-11-18 DE DE19691957961 patent/DE1957961A1/de active Pending
- 1969-11-18 FR FR6939572A patent/FR2023553A1/fr not_active Withdrawn
1971
- 1971-08-12 NO NO03021/71A patent/NO127349B/no unknown
1972
- 1972-09-18 SE SE7212032A patent/SE398748B/xx unknown

Also Published As

Publication number	Publication date
BE741765A (fi)	1970-05-19
SE367198B (fi)	1974-05-20
NO127349B (fi)	1973-06-12
NL6916954A (fi)	1970-05-20
GB1233828A (fi)	1971-06-03
IL33251A0 (en)	1969-12-31
ES373596A1 (es)	1973-04-16
DE1957961A1 (de)	1970-06-18
FI50626B (fi)	1976-02-02
AT294839B (de)	1971-12-10
BR6914223D0 (pt)	1973-02-08
SE398748B (sv)	1978-01-16
CH526557A (de)	1972-08-15
FR2023553A1 (fi)	1970-08-21
YU34206B (en)	1979-02-28
FI50626C (fi)	1976-05-10
YU287869A (en)	1978-06-30

Publication	Publication Date	Title
US8969561B2 (en)	2015-03-03	Apixaban preparation process
NO760401L (fi)	1976-08-17
NO147914B (no)	1983-03-28	Mellomprodukt ved fremstilling av farmakologisk aktive imidazol (1,5-a)(1,4)diazepinforbindelser
US3963736A (en)	1976-06-15	Preparation of 1-(lower alkyl)-1,4-dihydro-7-methyl-4-oxo-1,8-naphthyridine-3-carboxylic acids
NO148455B (no)	1983-07-04	Fremgangsmaate ved fremstilling av diazepin-derivater
NO170987B (no)	1992-09-28	Fremgangsmaate for avsvovling av jern
NO121951B (fi)	1971-05-03
NO126625B (fi)	1973-03-05
NO803160L (no)	1978-08-07	Pyrimidin-derivater.
NO120370B (fi)	1970-10-12
US3910911A (en)	1975-10-07	Production of quinazolinone compounds
US3128286A (en)	1964-04-07	Process for preparing analogues
Goncharov et al.	2009	Synthesis of Pyridin-2 (1H)-ones by the Intramolecular Cyclization of Amides of β-Enamino Ketones.
US3354206A (en)	1967-11-21	10, 11-dihydro-5-hydroxy-5-vinyl-5h-dibenzo-[a, d] cycloheptenes
NO165419B (no)	1990-10-29	Innretning for laasing og frigjoering av gjenstander beregnet for offentlig bruk, saasom bagasjetraller.
NO132800B (fi)	1975-09-29
NO123037B (fi)	1971-09-20
Tabei et al.	1979	Reaction of γ-Bromoacetoacetyl Bromide with N-Phenylhydroxylamine Derivatives: Synthesis of 1, 2-Oxazine Derivatives
US3170930A (en)	1965-02-23	Derivatives of dibenzo[1, 4, 5]thiadiazepine, dibenzo[1, 4, 5]oxadiazepine and dibenzo[1, 2, 5]triazepine
US3314962A (en)	1967-04-18	Ethynylated quinolizinium
US3499894A (en)	1970-03-10	Substituted 3,4 - dihydro - 2h - (1)-benzothieno - (3,2-b) - pyran-2-yl-amine compounds and method of preparation thereof
US3152139A (en)	1964-10-06	Certain aminoisoxazolone derivatives
NO822445L (no)	1983-01-17	Fremgangsmaate ved fremstilling av 6-(3,6-dihydro-1(2h)-pyridyl)-pyrimidin-3-oksyder
KR810001979B1 (ko)	1981-12-08	2, 5-디히드로-1, 2-티아지노 [5, 6-b] 인돌-3-카복사미드1, 1-디옥사이드의 제조방법
SU453840A3 (fi)	1974-12-15