FI62837C - Foerfarande foer framstaellning av nya terapeutiskt anvaendbara pyrano(4,3-e)-as-triaziner och deras 4-oxider - Google Patents

Foerfarande foer framstaellning av nya terapeutiskt anvaendbara pyrano(4,3-e)-as-triaziner och deras 4-oxider Download PDF

Info

Publication number: FI62837C
Authority: FI; Finland
Prior art keywords: group; compound; trifluoromethyl; formula; tert
Prior art date: 1977-03-18

Application number

FI780758A

Other languages

English (en)

Finnish (fi)

Other versions

FI780758A7 (fi

FI62837B (fi

Inventor

Gregory Benjamin Bennett

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.)

1977-03-18

Filing date

1978-03-09

Publication date

1983-03-10

1978-03-09 Application filed by Sandoz Ag filed Critical Sandoz Ag

1978-09-19 Publication of FI780758A7 publication Critical patent/FI780758A7/fi

1982-11-30 Application granted granted Critical

1982-11-30 Publication of FI62837B publication Critical patent/FI62837B/fi

1983-03-10 Publication of FI62837C publication Critical patent/FI62837C/fi

Links

230000001225 therapeutic effect Effects 0.000 title 2
150000001875 compounds Chemical class 0.000 claims description 30
238000000034 method Methods 0.000 claims description 15
125000004432 carbon atom Chemical group C* 0.000 claims description 12
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 12
125000000217 alkyl group Chemical group 0.000 claims description 9
125000001309 chloro group Chemical group Cl* 0.000 claims description 9
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 9
229910052801 chlorine Inorganic materials 0.000 claims description 8
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 8
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 7
125000003545 alkoxy group Chemical group 0.000 claims description 7
239000012298 atmosphere Substances 0.000 claims description 7
239000011737 fluorine Substances 0.000 claims description 7
229910052731 fluorine Inorganic materials 0.000 claims description 7
239000003960 organic solvent Substances 0.000 claims description 7
238000002360 preparation method Methods 0.000 claims description 7
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 6
125000003277 amino group Chemical group 0.000 claims description 6
HGCIXCUEYOPUTN-UHFFFAOYSA-N cyclohexene Chemical compound C1CCC=CC1 HGCIXCUEYOPUTN-UHFFFAOYSA-N 0.000 claims description 6
239000001257 hydrogen Substances 0.000 claims description 6
229910052739 hydrogen Inorganic materials 0.000 claims description 6
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 5
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 5
-1 m-trifluoromethylphenyl Chemical group 0.000 claims description 4
239000007858 starting material Substances 0.000 claims description 4
239000003054 catalyst Substances 0.000 claims description 3
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 3
229910000510 noble metal Inorganic materials 0.000 claims description 3
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 2
MGADZUXDNSDTHW-UHFFFAOYSA-N 2H-pyran Chemical compound C1OC=CC=C1 MGADZUXDNSDTHW-UHFFFAOYSA-N 0.000 claims 1
229920002472 Starch Polymers 0.000 claims 1
239000003086 colorant Substances 0.000 claims 1
229910052751 metal Inorganic materials 0.000 claims 1
239000002184 metal Substances 0.000 claims 1
239000008107 starch Substances 0.000 claims 1
125000005415 substituted alkoxy group Chemical group 0.000 claims 1
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 10
239000000203 mixture Substances 0.000 description 9
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 8
238000002474 experimental method Methods 0.000 description 8
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
229910052757 nitrogen Inorganic materials 0.000 description 5
238000012360 testing method Methods 0.000 description 5
XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 4
241000282693 Cercopithecidae Species 0.000 description 4
OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 4
241000699670 Mus sp. Species 0.000 description 4
GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 4
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 4
239000002253 acid Substances 0.000 description 4
238000010171 animal model Methods 0.000 description 4
230000035484 reaction time Effects 0.000 description 4
150000003839 salts Chemical group 0.000 description 4
239000002904 solvent Substances 0.000 description 4
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 3
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
238000006243 chemical reaction Methods 0.000 description 3
239000012458 free base Substances 0.000 description 3
239000000932 sedative agent Substances 0.000 description 3
230000001624 sedative effect Effects 0.000 description 3
239000000243 solution Substances 0.000 description 3
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 3
ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical compound OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-N 0.000 description 3
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
GQPLMRYTRLFLPF-UHFFFAOYSA-N Nitrous Oxide Chemical compound [O-][N+]#N GQPLMRYTRLFLPF-UHFFFAOYSA-N 0.000 description 2
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
150000007513 acids Chemical class 0.000 description 2
229910052786 argon Inorganic materials 0.000 description 2
150000004945 aromatic hydrocarbons Chemical class 0.000 description 2
VEQAGSPCZANNDR-UHFFFAOYSA-N azepine-1-sulfonamide Chemical compound NS(=O)(=O)N1C=CC=CC=C1 VEQAGSPCZANNDR-UHFFFAOYSA-N 0.000 description 2
WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 description 2
229910052799 carbon Inorganic materials 0.000 description 2
239000003153 chemical reaction reagent Substances 0.000 description 2
230000000052 comparative effect Effects 0.000 description 2
230000000694 effects Effects 0.000 description 2
238000001704 evaporation Methods 0.000 description 2
239000001307 helium Substances 0.000 description 2
229910052734 helium Inorganic materials 0.000 description 2
SWQJXJOGLNCZEY-UHFFFAOYSA-N helium atom Chemical compound [He] SWQJXJOGLNCZEY-UHFFFAOYSA-N 0.000 description 2
230000000144 pharmacologic effect Effects 0.000 description 2
BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
230000011514 reflex Effects 0.000 description 2
239000007787 solid Substances 0.000 description 2
BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
WRBBWSOGXARWPD-UHFFFAOYSA-N 4-hydroxyiminooctan-3-one Chemical compound CCCCC(C(CC)=O)=NO WRBBWSOGXARWPD-UHFFFAOYSA-N 0.000 description 1
229910015900 BF3 Inorganic materials 0.000 description 1
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
241000282668 Cebus Species 0.000 description 1
KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 description 1
206010062519 Poor quality sleep Diseases 0.000 description 1
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
241000906446 Theraps Species 0.000 description 1
KLBQZWRITKRQQV-UHFFFAOYSA-N Thioridazine Chemical compound C12=CC(SC)=CC=C2SC2=CC=CC=C2N1CCC1CCCCN1C KLBQZWRITKRQQV-UHFFFAOYSA-N 0.000 description 1
230000001773 anti-convulsant effect Effects 0.000 description 1
239000001961 anticonvulsive agent Substances 0.000 description 1
229960003965 antiepileptics Drugs 0.000 description 1
230000006399 behavior Effects 0.000 description 1
150000001559 benzoic acids Chemical class 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
210000004556 brain Anatomy 0.000 description 1
239000012267 brine Substances 0.000 description 1
239000002775 capsule Substances 0.000 description 1
239000000969 carrier Substances 0.000 description 1
WORJEOGGNQDSOE-UHFFFAOYSA-N chloroform;methanol Chemical compound OC.ClC(Cl)Cl WORJEOGGNQDSOE-UHFFFAOYSA-N 0.000 description 1
230000003111 delayed effect Effects 0.000 description 1
238000011161 development 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
238000000537 electroencephalography Methods 0.000 description 1
230000008020 evaporation Effects 0.000 description 1
239000000706 filtrate Substances 0.000 description 1
238000001914 filtration Methods 0.000 description 1
UYXAWHWODHRRMR-UHFFFAOYSA-N hexobarbital Chemical compound O=C1N(C)C(=O)NC(=O)C1(C)C1=CCCCC1 UYXAWHWODHRRMR-UHFFFAOYSA-N 0.000 description 1
229960002456 hexobarbital Drugs 0.000 description 1
229910000040 hydrogen fluoride Inorganic materials 0.000 description 1
230000000147 hypnotic effect Effects 0.000 description 1
239000000411 inducer Substances 0.000 description 1
230000001939 inductive effect Effects 0.000 description 1
229910052500 inorganic mineral Inorganic materials 0.000 description 1
239000010410 layer Substances 0.000 description 1
239000010985 leather Substances 0.000 description 1
229910052943 magnesium sulfate Inorganic materials 0.000 description 1
235000019341 magnesium sulphate Nutrition 0.000 description 1
150000002689 maleic acids Chemical class 0.000 description 1
238000004519 manufacturing process Methods 0.000 description 1
239000011707 mineral Substances 0.000 description 1
235000010755 mineral Nutrition 0.000 description 1
150000004682 monohydrates Chemical class 0.000 description 1
238000006396 nitration reaction Methods 0.000 description 1
229910017604 nitric acid Inorganic materials 0.000 description 1
LYGJENNIWJXYER-UHFFFAOYSA-N nitromethane Chemical compound C[N+]([O-])=O LYGJENNIWJXYER-UHFFFAOYSA-N 0.000 description 1
IOVCWXUNBOPUCH-UHFFFAOYSA-O nitrosooxidanium Chemical compound [OH2+]N=O IOVCWXUNBOPUCH-UHFFFAOYSA-O 0.000 description 1
239000001272 nitrous oxide Substances 0.000 description 1
150000007524 organic acids Chemical class 0.000 description 1
235000005985 organic acids Nutrition 0.000 description 1
239000012044 organic layer Substances 0.000 description 1
229910052763 palladium Inorganic materials 0.000 description 1
230000000803 paradoxical effect Effects 0.000 description 1
239000000546 pharmaceutical excipient Substances 0.000 description 1
239000002504 physiological saline solution Substances 0.000 description 1
229910052697 platinum Inorganic materials 0.000 description 1
125000006239 protecting group Chemical group 0.000 description 1
239000012429 reaction media Substances 0.000 description 1
238000011160 research Methods 0.000 description 1
230000000284 resting effect Effects 0.000 description 1
229910052703 rhodium Inorganic materials 0.000 description 1
239000010948 rhodium Substances 0.000 description 1
MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 description 1
229920006395 saturated elastomer Polymers 0.000 description 1
229940125723 sedative agent Drugs 0.000 description 1
239000000741 silica gel Substances 0.000 description 1
229910002027 silica gel Inorganic materials 0.000 description 1
235000017557 sodium bicarbonate Nutrition 0.000 description 1
229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
238000010561 standard procedure Methods 0.000 description 1
239000000126 substance Substances 0.000 description 1
150000003444 succinic acids Chemical class 0.000 description 1
229960002784 thioridazine Drugs 0.000 description 1
IECKAVQTURBPON-UHFFFAOYSA-N trimethoxymethylbenzene Chemical compound COC(OC)(OC)C1=CC=CC=C1 IECKAVQTURBPON-UHFFFAOYSA-N 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
- C07D491/08—Bridged systems
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/20—Hypnotics; Sedatives

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Medicinal Chemistry (AREA)
Anesthesiology (AREA)
Neurology (AREA)
Neurosurgery (AREA)
Bioinformatics & Cheminformatics (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Engineering & Computer Science (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Biomedical Technology (AREA)
Pharmacology & Pharmacy (AREA)
Life Sciences & Earth Sciences (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)
Saccharide Compounds (AREA)

FI780758A 1977-03-18 1978-03-09 Foerfarande foer framstaellning av nya terapeutiskt anvaendbara pyrano(4,3-e)-as-triaziner och deras 4-oxider FI62837C (fi)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US77907177A	1977-03-18	1977-03-18
US77907177		1977-03-18

Publications (3)

Publication Number	Publication Date
FI780758A7 FI780758A7 (fi)	1978-09-19
FI62837B FI62837B (fi)	1982-11-30
FI62837C true FI62837C (fi)	1983-03-10

Family

ID=25115233

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
FI780758A FI62837C (fi)	1977-03-18	1978-03-09	Foerfarande foer framstaellning av nya terapeutiskt anvaendbara pyrano(4,3-e)-as-triaziner och deras 4-oxider

Country Status (19)

Country	Link
JP (1)	JPS53116400A (de)
AT (1)	AT366688B (de)
AU (1)	AU519623B2 (de)
BE (1)	BE864987A (de)
CA (1)	CA1095518A (de)
DE (1)	DE2810224A1 (de)
DK (1)	DK104978A (de)
ES (1)	ES467999A1 (de)
FI (1)	FI62837C (de)
FR (1)	FR2383947A1 (de)
GB (1)	GB1597924A (de)
IE (1)	IE46679B1 (de)
IL (1)	IL54295A (de)
IT (1)	IT7848478A0 (de)
NL (1)	NL7802746A (de)
NZ (1)	NZ186713A (de)
PT (1)	PT67791A (de)
SE (1)	SE7802773L (de)
ZA (1)	ZA781587B (de)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4233469A (en) *	1979-02-13	1980-11-11	Steppe Theodore W	Conduit bushing

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DK139301B (da) *	1974-05-01	1979-01-29	Sandoz Ag	Analogifremgangsmåde til fremstilling af 5,5,7,7-tetramethylfuro(3,4-e)as-triaziner.

1978
- 1978-03-09 FI FI780758A patent/FI62837C/fi not_active IP Right Cessation
- 1978-03-09 DE DE19782810224 patent/DE2810224A1/de not_active Withdrawn
- 1978-03-09 DK DK104978A patent/DK104978A/da not_active Application Discontinuation
- 1978-03-10 SE SE7802773A patent/SE7802773L/xx unknown
- 1978-03-14 NL NL7802746A patent/NL7802746A/xx not_active Application Discontinuation
- 1978-03-15 GB GB10254/78A patent/GB1597924A/en not_active Expired
- 1978-03-16 IL IL54295A patent/IL54295A/xx unknown
- 1978-03-16 CA CA299,081A patent/CA1095518A/en not_active Expired
- 1978-03-16 IE IE540/78A patent/IE46679B1/en unknown
- 1978-03-16 BE BE186013A patent/BE864987A/xx not_active IP Right Cessation
- 1978-03-16 JP JP2936378A patent/JPS53116400A/ja active Pending
- 1978-03-16 NZ NZ186713A patent/NZ186713A/xx unknown
- 1978-03-16 AU AU34224/78A patent/AU519623B2/en not_active Expired
- 1978-03-17 IT IT7848478A patent/IT7848478A0/it unknown
- 1978-03-17 PT PT67791A patent/PT67791A/pt unknown
- 1978-03-17 ES ES467999A patent/ES467999A1/es not_active Expired
- 1978-03-17 AT AT0189678A patent/AT366688B/de not_active IP Right Cessation
- 1978-03-17 ZA ZA00781587A patent/ZA781587B/xx unknown
- 1978-03-17 FR FR7807768A patent/FR2383947A1/fr active Granted

Also Published As

Publication number	Publication date
IE780540L (en)	1978-09-18
ES467999A1 (es)	1979-09-01
NL7802746A (nl)	1978-09-20
IL54295A0 (en)	1978-06-15
GB1597924A (en)	1981-09-16
BE864987A (fr)	1978-09-18
IE46679B1 (en)	1983-08-24
AU3422478A (en)	1979-09-20
IL54295A (en)	1981-02-27
DE2810224A1 (de)	1978-09-28
IT7848478A0 (it)	1978-03-17
FR2383947A1 (fr)	1978-10-13
JPS53116400A (en)	1978-10-11
FI780758A7 (fi)	1978-09-19
NZ186713A (en)	1980-09-12
DK104978A (da)	1978-09-19
ZA781587B (en)	1979-10-31
CA1095518A (en)	1981-02-10
FI62837B (fi)	1982-11-30
ATA189678A (de)	1981-09-15
AU519623B2 (en)	1981-12-17
FR2383947B1 (de)	1981-07-03
AT366688B (de)	1982-04-26
PT67791A (fr)	1978-04-01
SE7802773L (sv)	1978-09-19

Legal Events

Date	Code	Title	Description
2004-08-31	MM	Patent lapsed	Owner name: SANDOZ AG

Publication	Publication Date	Title
US3987179A (en)	1976-10-19	Isoxazolyl benzamides as pharmacological agents
ITMI961732A1 (it)	1998-02-09	Uso di ammidi dell'acido gamma-idrossibutirrico nel trattamento di tossicodipendenze e in particolare dell'alcoolismo
FI67686C (fi)	1985-05-10	Foerfarande foer framstaellning av nya terapeutiskt anvaendbara fenetanolaminderivat
WO1990012574A1 (en)	1990-11-01	Dopamine agonist compounds
US6376516B1 (en)	2002-04-23	Noscapine and noscapine derivatives, useful as anticancer agents
FI62837C (fi)	1983-03-10	Foerfarande foer framstaellning av nya terapeutiskt anvaendbara pyrano(4,3-e)-as-triaziner och deras 4-oxider
CA2248826A1 (en)	1997-08-21	Naphthoquinone antitumor compound and method
US3455985A (en)	1969-07-15	2-(alpha-amino-lower alkanoyl amino)benzophenones
IE61437B1 (en)	1994-11-02	Anticonvulsant composition containing amino acid derivative and use of said amino acid derivative
US3248292A (en)	1966-04-26	Pharmaceutically active dimethoxyquinazolines
US3920687A (en)	1975-11-18	2,3,6,7-tetrahydro-6-phenyl-5h-imidazo(1,2-d)+8 1,4)benzodiazepin-5-ones and diazepines
FI57416C (fi)	1980-08-11	Foerfarande foer framstaellning av terapeutiskt anvaendbara nya 5,5,7,7-tetrametylfuro(3,4-e)-as-triaziner
US4162257A (en)	1979-07-24	N,N-dimethyl-5-phenyl-2-furamides
CA1101421A (en)	1981-05-19	Pyrano¬4,3-e\| -as-triazines, their production and tranquilliser/sleep-inducer use
US3963713A (en)	1976-06-15	Furo(3,4-e)-as-triazines and corresponding 4-oxides
US3962240A (en)	1976-06-08	Process for the preparation of furo(3,4-e)-as-triazines
US4013679A (en)	1977-03-22	Substituted 6,7-dihydro [1,7-ab](1) benzazepine compounds
US4055643A (en)	1977-10-25	Furo(3,4-E)-as-triazines and corresponding 4-oxides as sleep inducers and minor tranquilizers
US4866073A (en)	1989-09-12	Acridinylmethylamino derivatives and pharmaceutical compositions containing them
NZ189537A (en)	1983-02-15	Cup selection apparatus for vending machine
US4228280A (en)	1980-10-14	Pyrano[4,3-e]-as-triazines and corresponding 4-oxides
EP0246077A1 (de)	1987-11-19	Heteropolyzyklische aromatische Verbindungen
US3856787A (en)	1974-12-24	1-substituted-2-thio-1h-1,4-benzodiazepines
GB2139225A (en)	1984-11-07	Novel acylaminophenol derivatives
US3859285A (en)	1975-01-07	10, 11-dihydro-5h-benzo (4,5) cyclohepta (1,2-b) pyrazines