NO760764L - - Google Patents

Info

Publication number: NO760764L
Authority: NO; Norway
Prior art keywords: formula; compounds; methyl; hours; manner known
Prior art date: 1975-03-14

Application number

NO760764A

Other languages

English (en)

Norwegian (no)

Inventor

J Nadelson

Original Assignee

Sandoz Ag

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.)

1975-03-14

Filing date

1976-03-05

Publication date

1976-09-15

1976-03-05 Application filed by Sandoz Ag filed Critical Sandoz Ag

1976-09-15 Publication of NO760764L publication Critical patent/NO760764L/no

Links

150000001875 compounds Chemical class 0.000 claims description 39
229910052739 hydrogen Inorganic materials 0.000 claims description 9
239000001257 hydrogen Substances 0.000 claims description 9
238000000034 method Methods 0.000 claims description 8
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 6
239000000460 chlorine Substances 0.000 claims description 6
229910052801 chlorine Inorganic materials 0.000 claims description 6
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 5
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 4
125000000217 alkyl group Chemical group 0.000 claims description 4
125000004432 carbon atom Chemical group C* 0.000 claims description 4
229910052731 fluorine Inorganic materials 0.000 claims description 4
239000011737 fluorine Substances 0.000 claims description 4
239000003960 organic solvent Substances 0.000 claims description 4
238000002360 preparation method Methods 0.000 claims description 3
125000003545 alkoxy group Chemical group 0.000 claims description 2
125000004435 hydrogen atom Chemical class [H]* 0.000 claims 1
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 15
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 15
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 10
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
239000000203 mixture Substances 0.000 description 7
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 6
239000002253 acid Substances 0.000 description 6
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 5
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 4
MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 4
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
150000002431 hydrogen Chemical class 0.000 description 4
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
230000035484 reaction time Effects 0.000 description 4
150000003839 salts Chemical class 0.000 description 4
230000001624 sedative effect Effects 0.000 description 4
239000007858 starting material Substances 0.000 description 4
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 3
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 3
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
-1 alkali metal salts Chemical class 0.000 description 3
239000003054 catalyst Substances 0.000 description 3
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 3
239000000932 sedative agent Substances 0.000 description 3
239000007787 solid Substances 0.000 description 3
239000000725 suspension Substances 0.000 description 3
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
150000007513 acids Chemical class 0.000 description 2
HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 2
229940117975 chromium trioxide Drugs 0.000 description 2
WGLPBDUCMAPZCE-UHFFFAOYSA-N chromium trioxide Inorganic materials O=[Cr](=O)=O WGLPBDUCMAPZCE-UHFFFAOYSA-N 0.000 description 2
GAMDZJFZMJECOS-UHFFFAOYSA-N chromium(6+);oxygen(2-) Chemical compound [O-2].[O-2].[O-2].[Cr+6] GAMDZJFZMJECOS-UHFFFAOYSA-N 0.000 description 2
238000005984 hydrogenation reaction Methods 0.000 description 2
238000004519 manufacturing process Methods 0.000 description 2
238000010992 reflux Methods 0.000 description 2
239000002904 solvent Substances 0.000 description 2
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
230000007306 turnover Effects 0.000 description 2
GHJOYRMAYLLOIO-UHFFFAOYSA-N 3,5-dimethyl-1,2-oxazole-4-carboxamide Chemical compound CC1=NOC(C)=C1C(N)=O GHJOYRMAYLLOIO-UHFFFAOYSA-N 0.000 description 1
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical class [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 1
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 1
WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
239000007868 Raney catalyst Substances 0.000 description 1
NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 description 1
229910000564 Raney nickel Inorganic materials 0.000 description 1
241000906446 Theraps Species 0.000 description 1
230000002378 acidificating effect Effects 0.000 description 1
150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
229910052783 alkali metal Inorganic materials 0.000 description 1
229910052784 alkaline earth metal Inorganic materials 0.000 description 1
150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
238000009835 boiling Methods 0.000 description 1
159000000007 calcium salts Chemical class 0.000 description 1
239000002775 capsule Substances 0.000 description 1
239000000969 carrier Substances 0.000 description 1
230000003197 catalytic effect Effects 0.000 description 1
238000006243 chemical reaction Methods 0.000 description 1
239000003085 diluting agent Substances 0.000 description 1
239000003814 drug Substances 0.000 description 1
229940079593 drug Drugs 0.000 description 1
230000000694 effects Effects 0.000 description 1
150000002170 ethers Chemical class 0.000 description 1
238000001704 evaporation Methods 0.000 description 1
230000008020 evaporation Effects 0.000 description 1
238000002474 experimental method Methods 0.000 description 1
238000001914 filtration Methods 0.000 description 1
125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
230000000147 hypnotic effect Effects 0.000 description 1
238000011065 in-situ storage Methods 0.000 description 1
230000006698 induction Effects 0.000 description 1
230000001939 inductive effect Effects 0.000 description 1
239000012442 inert solvent Substances 0.000 description 1
230000000977 initiatory effect Effects 0.000 description 1
229910052500 inorganic mineral Inorganic materials 0.000 description 1
229910052744 lithium Inorganic materials 0.000 description 1
239000011777 magnesium Substances 0.000 description 1
229910052749 magnesium Inorganic materials 0.000 description 1
235000010755 mineral Nutrition 0.000 description 1
239000011707 mineral Substances 0.000 description 1
MAFGERLXTNIVPA-UHFFFAOYSA-N n-methyl-5-phenacyl-3-phenyl-1,2-oxazole-4-carboxamide Chemical compound O1N=C(C=2C=CC=CC=2)C(C(=O)NC)=C1CC(=O)C1=CC=CC=C1 MAFGERLXTNIVPA-UHFFFAOYSA-N 0.000 description 1
150000007524 organic acids Chemical class 0.000 description 1
235000005985 organic acids Nutrition 0.000 description 1
150000002894 organic compounds Chemical class 0.000 description 1
230000003647 oxidation Effects 0.000 description 1
238000007254 oxidation reaction Methods 0.000 description 1
230000001590 oxidative effect Effects 0.000 description 1
MUMZUERVLWJKNR-UHFFFAOYSA-N oxoplatinum Chemical compound [Pt]=O MUMZUERVLWJKNR-UHFFFAOYSA-N 0.000 description 1
QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 1
239000003208 petroleum Substances 0.000 description 1
239000000546 pharmaceutical excipient Substances 0.000 description 1
230000003285 pharmacodynamic effect Effects 0.000 description 1
229910003446 platinum oxide Inorganic materials 0.000 description 1
229920000137 polyphosphoric acid Polymers 0.000 description 1
239000012286 potassium permanganate Substances 0.000 description 1
159000000001 potassium salts Chemical class 0.000 description 1
239000012429 reaction media Substances 0.000 description 1
239000011541 reaction mixture Substances 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
239000011734 sodium Substances 0.000 description 1
239000011780 sodium chloride Substances 0.000 description 1
159000000000 sodium salts Chemical class 0.000 description 1
239000000126 substance Substances 0.000 description 1
LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom 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 ring carbon atoms
- C07D213/62—Oxygen or sulfur atoms
- C07D213/69—Two or more oxygen atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D261/00—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings
- C07D261/02—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings
- C07D261/06—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings having two or more double bonds between ring members or between ring members and non-ring members
- C07D261/10—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings having two or more double bonds between ring members or between ring members and non-ring members 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 ring carbon atoms
- C07D261/18—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Pyridine Compounds (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Plural Heterocyclic Compounds (AREA)

NO760764A 1975-03-14 1976-03-05 NO760764L (da)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US55841975A	1975-03-14	1975-03-14
US58476475A	1975-06-09	1975-06-09

Publications (1)

Publication Number	Publication Date
NO760764L true NO760764L (da)	1976-09-15

Family

ID=27071738

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NO760764A NO760764L (da)	1975-03-14	1976-03-05

Country Status (21)

Country	Link
JP (1)	JPS51113877A (da)
AT (1)	AT358590B (da)
AU (1)	AU505460B2 (da)
CA (1)	CA1064038A (da)
CH (1)	CH601241A5 (da)
DE (1)	DE2609127A1 (da)
DK (1)	DK98176A (da)
ES (1)	ES446035A1 (da)
FI (1)	FI760572A7 (da)
FR (2)	FR2303545A1 (da)
GB (3)	GB1545575A (da)
HK (2)	HK46581A (da)
IE (1)	IE43907B1 (da)
IL (1)	IL49202A (da)
MY (2)	MY8200141A (da)
NL (1)	NL7602494A (da)
NO (1)	NO760764L (da)
NZ (1)	NZ180299A (da)
PT (1)	PT64899B (da)
SE (1)	SE7602542L (da)
YU (1)	YU63676A (da)

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4179566A (en) *	1975-08-06	1979-12-18	Sandoz, Inc.	Substituted hydroxy pyridones
US4238616A (en) *	1977-01-19	1980-12-09	Sandoz, Inc.	3-(Substituted)phenyl-5-(β-hydroxyphenethyl)-N-(alkyl)-isoxazole-4-carboxamides
WO2002102807A1 (en) *	2001-06-14	2002-12-27	Banyu Pharmaceutical Co., Ltd.	Novel isoxazolopyridone derivatives and use thereof
GB0119911D0 (en)	2001-08-15	2001-10-10	Novartis Ag	Organic Compounds

1976
- 1976-02-26 SE SE7602542A patent/SE7602542L/xx not_active Application Discontinuation
- 1976-03-02 CH CH255876A patent/CH601241A5/xx not_active IP Right Cessation
- 1976-03-05 FI FI760572A patent/FI760572A7/fi not_active Application Discontinuation
- 1976-03-05 NO NO760764A patent/NO760764L/no unknown
- 1976-03-05 DE DE19762609127 patent/DE2609127A1/de not_active Withdrawn
- 1976-03-05 DK DK98176*#A patent/DK98176A/da unknown
- 1976-03-09 GB GB9317/76A patent/GB1545575A/en not_active Expired
- 1976-03-09 GB GB38667/78A patent/GB1545576A/en not_active Expired
- 1976-03-09 GB GB38668/78A patent/GB1545577A/en not_active Expired
- 1976-03-10 NL NL7602494A patent/NL7602494A/xx not_active Application Discontinuation
- 1976-03-10 FR FR7606827A patent/FR2303545A1/fr active Granted
- 1976-03-11 YU YU00636/76A patent/YU63676A/xx unknown
- 1976-03-12 PT PT64899A patent/PT64899B/pt unknown
- 1976-03-12 IL IL49202A patent/IL49202A/xx unknown
- 1976-03-12 CA CA247,763A patent/CA1064038A/en not_active Expired
- 1976-03-12 AT AT181576A patent/AT358590B/de not_active IP Right Cessation
- 1976-03-12 JP JP51026228A patent/JPS51113877A/ja active Pending
- 1976-03-12 ES ES446035A patent/ES446035A1/es not_active Expired
- 1976-03-12 NZ NZ180299A patent/NZ180299A/xx unknown
- 1976-03-12 IE IE528/76A patent/IE43907B1/en unknown
- 1976-03-15 AU AU12012/76A patent/AU505460B2/en not_active Ceased
- 1976-11-30 FR FR7636022A patent/FR2371435A1/fr active Granted
1981
- 1981-09-17 HK HK465/81A patent/HK46581A/xx unknown
- 1981-09-17 HK HK466/81A patent/HK46681A/xx unknown
1982
- 1982-12-30 MY MY141/82A patent/MY8200141A/xx unknown
- 1982-12-30 MY MY142/82A patent/MY8200142A/xx unknown

Also Published As

Publication number	Publication date
HK46681A (en)	1981-09-25
YU63676A (en)	1982-02-28
FR2371435B1 (da)	1980-03-07
DE2609127A1 (de)	1976-09-23
SE7602542L (sv)	1976-09-15
GB1545575A (en)	1979-05-10
GB1545577A (en)	1979-05-10
PT64899B (fr)	1977-08-18
CH601241A5 (da)	1978-06-30
GB1545576A (en)	1979-05-10
MY8200141A (en)	1982-12-31
CA1064038A (en)	1979-10-09
AU505460B2 (en)	1979-11-22
NL7602494A (nl)	1976-09-16
IE43907B1 (en)	1981-07-01
PT64899A (fr)	1976-04-01
JPS51113877A (en)	1976-10-07
FI760572A7 (da)	1976-09-15
MY8200142A (en)	1982-12-31
FR2303545A1 (fr)	1976-10-08
ATA181576A (de)	1980-02-15
IL49202A (en)	1979-09-30
IE43907L (en)	1976-09-14
FR2303545B1 (da)	1982-03-19
FR2371435A1 (fr)	1978-06-16
ES446035A1 (es)	1977-09-16
NZ180299A (en)	1978-07-28
AU1201276A (en)	1977-09-22
DK98176A (da)	1976-09-15
AT358590B (de)	1980-09-25
HK46581A (en)	1981-09-25
IL49202A0 (en)	1976-05-31

Publication	Publication Date	Title
Adams et al.	1952	Ultraviolet spectra and structures of the pyrido [1, 2-a] pyrimidones
Robison et al.	1956	The Rearrangement of Isoquinoline-n-oxides
NO134212B (da)	1976-05-24
US4217349A (en)	1980-08-12	Benzisoxazole derivatives
US4016281A (en)	1977-04-05	Tetralone and indanone compounds
NO129745B (da)	1974-05-20
US4122176A (en)	1978-10-24	3-(Piperazinoalkyl)-benz-2,1-isoxazoles
GB2055360A (en)	1981-03-04	Benzimidazoles
NO752939L (da)	1976-03-02
US4975431A (en)	1990-12-04	Certain anti-inflammatory cyclohepta[b]pyridines and analogs thereof
Popp et al.	1968	Reissert compound studies. XVIII. Analogs derived from chloroformates
US3308121A (en)	1967-03-07	3-morpholinones, thiones and 5, 6 oxazines
US4024262A (en)	1977-05-17	Substituted hydroxy pyridones
NZ204369A (en)	1986-09-10	Piperazine derivatives,their production,and pharmaceutical compositions which contain them
US4179566A (en)	1979-12-18	Substituted hydroxy pyridones
EP0001002A1 (en)	1979-03-07	Indanamines, processes for their preparation and compositions containing them
US4060533A (en)	1977-11-29	Pyranone carboxamides
Settimj et al.	1988	β‐Carbolines as agonistic or antagonistic benzodiazepine receptor ligands. 1. Synthesis of some 5‐, 6‐and 7‐amino derivatives of 3‐methoxycarbonyl‐β‐carboline (β‐CCM) and of 3‐ethoxycarbonyl‐β‐carboline (β‐CCE)
EP0116268B1 (en)	1988-06-08	Novel quinazolinone derivative, a process for preparing the same and a pharmaceutical composition
US4064251A (en)	1977-12-20	Substituted hydroxy pyridones
US4122182A (en)	1978-10-24	Substituted hydroxy pyridones
IE43907B1 (en)	1981-07-01	3-(alpha-iminobenzyl)-4-hydroxy-2(1h)-pyridone derivatives
Huckle et al.	1971	4-Amino-2, 3, 4, 5-tetrahydro-1-benzoxepin-5-ols, 4-amino-2, 3, 4, 5-tetrahydro-1-benzothiepin-5-ols, and related compounds
US3657271A (en)	1972-04-18	1 3-dimethyl-5-methylamino-8-phenylpyrazolo(4 3-e)(1 4)diazepine
PARHAM et al.	1961	Reaction of Diazo Compounds with Nitroolefins. VII. The Thermal Decomposition of Nitropyrazolines