IL92055A - 3-(cycloalkyl substituted 1,2,4-oxadiazolyl)-4,5-dihydro-4-oxo-5- tertbutyl-imidaz (1,5-a) quinoxalines - Google Patents

3-(cycloalkyl substituted 1,2,4-oxadiazolyl)-4,5-dihydro-4-oxo-5- tertbutyl-imidaz (1,5-a) quinoxalines

Info

Publication number: IL92055A
Authority: IL; Israel
Prior art keywords: oxo; dihydro; compound; tert; binding
Prior art date: 1988-11-10

Application number

IL9205589A

Other languages

English (en)

Other versions

IL92055A0 (en

Original Assignee

Novo Nordisk As

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.)

1988-11-10

Filing date

1989-10-19

Publication date

1994-01-25

1989-10-19 Application filed by Novo Nordisk As filed Critical Novo Nordisk As

1990-07-12 Publication of IL92055A0 publication Critical patent/IL92055A0/xx

1994-01-25 Publication of IL92055A publication Critical patent/IL92055A/en

Links

150000003252 quinoxalines Chemical class 0.000 title description 2
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 5
239000001257 hydrogen Substances 0.000 claims abstract description 5
-1 -tert-butyl compound Chemical class 0.000 claims abstract description 3
150000001875 compounds Chemical class 0.000 claims description 29
229910052736 halogen Inorganic materials 0.000 claims description 3
150000002431 hydrogen Chemical class 0.000 claims description 3
125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims description 2
150000002367 halogens Chemical class 0.000 claims description 2
MVQHDTIAGNSFNE-UHFFFAOYSA-N 5-tert-butyl-3-(5-cyclopropyl-1,2,4-oxadiazol-3-yl)imidazo[1,5-a]quinoxalin-4-one Chemical compound C=12C(=O)N(C(C)(C)C)C3=CC=CC=C3N2C=NC=1C(N=1)=NOC=1C1CC1 MVQHDTIAGNSFNE-UHFFFAOYSA-N 0.000 claims 1
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 1
230000000144 pharmacologic effect Effects 0.000 abstract description 3
YELMWJNXDALKFE-UHFFFAOYSA-N 3h-imidazo[4,5-f]quinoxaline Chemical group N1=CC=NC2=C(NC=N3)C3=CC=C21 YELMWJNXDALKFE-UHFFFAOYSA-N 0.000 abstract description 2
238000006467 substitution reaction Methods 0.000 abstract description 2
238000001311 chemical methods and process Methods 0.000 abstract 1
230000020335 dealkylation Effects 0.000 abstract 1
238000006900 dealkylation reaction Methods 0.000 abstract 1
125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 1
238000012360 testing method Methods 0.000 description 20
230000027455 binding Effects 0.000 description 13
239000000126 substance Substances 0.000 description 13
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 11
230000009870 specific binding Effects 0.000 description 10
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
239000000243 solution Substances 0.000 description 9
XSCHRSMBECNVNS-UHFFFAOYSA-N quinoxaline Chemical compound N1=CC=NC2=CC=CC=C21 XSCHRSMBECNVNS-UHFFFAOYSA-N 0.000 description 8
241000699670 Mus sp. Species 0.000 description 7
239000013078 crystal Substances 0.000 description 7
229960002200 flunitrazepam Drugs 0.000 description 7
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
102000004300 GABA-A Receptors Human genes 0.000 description 5
108090000839 GABA-A Receptors Proteins 0.000 description 5
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
238000003556 assay Methods 0.000 description 4
210000004556 brain Anatomy 0.000 description 4
239000000203 mixture Substances 0.000 description 4
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 3
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
PPTYJKAXVCCBDU-UHFFFAOYSA-N Rohypnol Chemical compound N=1CC(=O)N(C)C2=CC=C([N+]([O-])=O)C=C2C=1C1=CC=CC=C1F PPTYJKAXVCCBDU-UHFFFAOYSA-N 0.000 description 3
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
239000003795 chemical substances by application Substances 0.000 description 3
239000012528 membrane Substances 0.000 description 3
239000000047 product Substances 0.000 description 3
239000002904 solvent Substances 0.000 description 3
241000283690 Bos taurus Species 0.000 description 2
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
239000001961 anticonvulsive agent Substances 0.000 description 2
230000000949 anxiolytic effect Effects 0.000 description 2
229940049706 benzodiazepine Drugs 0.000 description 2
239000003054 catalyst Substances 0.000 description 2
DGBIGWXXNGSACT-UHFFFAOYSA-N clonazepam Chemical compound C12=CC([N+](=O)[O-])=CC=C2NC(=O)CN=C1C1=CC=CC=C1Cl DGBIGWXXNGSACT-UHFFFAOYSA-N 0.000 description 2
229960003120 clonazepam Drugs 0.000 description 2
VJABZEOIUVAPNO-UHFFFAOYSA-N ethyl 2-(2-amino-n-tert-butylanilino)-2-oxoacetate Chemical compound CCOC(=O)C(=O)N(C(C)(C)C)C1=CC=CC=C1N VJABZEOIUVAPNO-UHFFFAOYSA-N 0.000 description 2
MYWIBLDQAWXUAD-UHFFFAOYSA-N ethyl 2-(n-tert-butyl-2-nitroanilino)-2-oxoacetate Chemical compound CCOC(=O)C(=O)N(C(C)(C)C)C1=CC=CC=C1[N+]([O-])=O MYWIBLDQAWXUAD-UHFFFAOYSA-N 0.000 description 2
239000003365 glass fiber Substances 0.000 description 2
238000000338 in vitro Methods 0.000 description 2
238000001727 in vivo Methods 0.000 description 2
230000005764 inhibitory process Effects 0.000 description 2
238000007912 intraperitoneal administration Methods 0.000 description 2
230000009871 nonspecific binding Effects 0.000 description 2
LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 2
238000002360 preparation method Methods 0.000 description 2
238000001953 recrystallisation Methods 0.000 description 2
238000003756 stirring Methods 0.000 description 2
239000000725 suspension Substances 0.000 description 2
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
SVUOLADPCWQTTE-UHFFFAOYSA-N 1h-1,2-benzodiazepine Chemical compound N1N=CC=CC2=CC=CC=C12 SVUOLADPCWQTTE-UHFFFAOYSA-N 0.000 description 1
BGHGVAKKIBOJGS-UHFFFAOYSA-N 5-cyclopropyl-3-(isocyanomethyl)-1,2,4-oxadiazole Chemical compound [C-]#[N+]CC1=NOC(C2CC2)=N1 BGHGVAKKIBOJGS-UHFFFAOYSA-N 0.000 description 1
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-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
235000004443 Ricinus communis Nutrition 0.000 description 1
241000251539 Vertebrata <Metazoa> Species 0.000 description 1
230000001773 anti-convulsant effect Effects 0.000 description 1
229940125681 anticonvulsant agent Drugs 0.000 description 1
229960003965 antiepileptics Drugs 0.000 description 1
239000002249 anxiolytic agent Substances 0.000 description 1
229940005530 anxiolytics Drugs 0.000 description 1
150000001557 benzodiazepines Chemical class 0.000 description 1
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
238000006243 chemical reaction Methods 0.000 description 1
238000001816 cooling Methods 0.000 description 1
235000019628 coolness Nutrition 0.000 description 1
230000002596 correlated effect Effects 0.000 description 1
239000012043 crude product Substances 0.000 description 1
125000000753 cycloalkyl group Chemical group 0.000 description 1
LGTLXDJOAJDFLR-UHFFFAOYSA-N diethyl chlorophosphate Chemical compound CCOP(Cl)(=O)OCC LGTLXDJOAJDFLR-UHFFFAOYSA-N 0.000 description 1
238000010790 dilution Methods 0.000 description 1
239000012895 dilution Substances 0.000 description 1
238000006073 displacement reaction Methods 0.000 description 1
231100000673 dose–response relationship Toxicity 0.000 description 1
230000000694 effects Effects 0.000 description 1
230000001804 emulsifying effect Effects 0.000 description 1
OWZFULPEVHKEKS-UHFFFAOYSA-N ethyl 2-chloro-2-oxoacetate Chemical compound CCOC(=O)C(Cl)=O OWZFULPEVHKEKS-UHFFFAOYSA-N 0.000 description 1
FPULFENIJDPZBX-UHFFFAOYSA-N ethyl 2-isocyanoacetate Chemical compound CCOC(=O)C[N+]#[C-] FPULFENIJDPZBX-UHFFFAOYSA-N 0.000 description 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
238000001704 evaporation 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
238000011534 incubation Methods 0.000 description 1
238000005567 liquid scintillation counting Methods 0.000 description 1
239000000155 melt Substances 0.000 description 1
HIGVOOQGROZGET-UHFFFAOYSA-N n-tert-butyl-2-nitroaniline Chemical compound CC(C)(C)NC1=CC=CC=C1[N+]([O-])=O HIGVOOQGROZGET-UHFFFAOYSA-N 0.000 description 1
239000012074 organic phase Substances 0.000 description 1
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
239000002504 physiological saline solution Substances 0.000 description 1
238000001556 precipitation Methods 0.000 description 1
210000004129 prosencephalon Anatomy 0.000 description 1
UPUZGXILYFKSGE-UHFFFAOYSA-N quinoxaline-2-carboxylic acid Chemical compound C1=CC=CC2=NC(C(=O)O)=CN=C21 UPUZGXILYFKSGE-UHFFFAOYSA-N 0.000 description 1
230000002285 radioactive effect Effects 0.000 description 1
102000005962 receptors Human genes 0.000 description 1
108020003175 receptors Proteins 0.000 description 1
238000010992 reflux Methods 0.000 description 1
238000003345 scintillation counting Methods 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
239000011734 sodium Substances 0.000 description 1
239000007787 solid Substances 0.000 description 1
230000003381 solubilizing effect Effects 0.000 description 1
239000012258 stirred mixture Substances 0.000 description 1
238000010998 test method Methods 0.000 description 1
239000012085 test solution Substances 0.000 description 1
MLGCXEBRWGEOQX-UHFFFAOYSA-N tetradifon Chemical compound C1=CC(Cl)=CC=C1S(=O)(=O)C1=CC(Cl)=C(Cl)C=C1Cl MLGCXEBRWGEOQX-UHFFFAOYSA-N 0.000 description 1
125000001544 thienyl group Chemical group 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed 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
- A61P25/08—Antiepileptics; Anticonvulsants
- 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)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Life Sciences & Earth Sciences (AREA)
Bioinformatics & Cheminformatics (AREA)
Biomedical Technology (AREA)
Neurology (AREA)
Neurosurgery (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Veterinary Medicine (AREA)
Pharmacology & Pharmacy (AREA)
Engineering & Computer Science (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Anesthesiology (AREA)
Pain & Pain Management (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Plural Heterocyclic Compounds (AREA)
Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)

IL9205589A 1988-11-10 1989-10-19 3-(cycloalkyl substituted 1,2,4-oxadiazolyl)-4,5-dihydro-4-oxo-5- tertbutyl-imidaz (1,5-a) quinoxalines IL92055A (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
DK626288A DK626288D0 (da)	1988-11-10	1988-11-10	Kemisk proces til fremstilling af imidazoquinoxaliner og mellemprodukter til brug i processen

Publications (2)

Publication Number	Publication Date
IL92055A0 IL92055A0 (en)	1990-07-12
IL92055A true IL92055A (en)	1994-01-25

Family

ID=8148369

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
IL9205589A IL92055A (en)	1988-11-10	1989-10-19	3-(cycloalkyl substituted 1,2,4-oxadiazolyl)-4,5-dihydro-4-oxo-5- tertbutyl-imidaz (1,5-a) quinoxalines

Country Status (17)

Country	Link
US (1)	US4999353A (de)
EP (1)	EP0368652B1 (de)
JP (1)	JPH02178285A (de)
AT (1)	ATE119162T1 (de)
AU (1)	AU622941B2 (de)
CA (1)	CA2002624A1 (de)
DE (1)	DE68921418T2 (de)
DK (1)	DK626288D0 (de)
ES (1)	ES2068903T3 (de)
FI (1)	FI92931C (de)
GR (1)	GR3015718T3 (de)
IE (1)	IE68939B1 (de)
IL (1)	IL92055A (de)
NO (1)	NO173827C (de)
NZ (1)	NZ231321A (de)
PT (1)	PT92279B (de)
ZA (1)	ZA898051B (de)

Families Citing this family (9)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DK588489D0 (da) *	1989-11-22	1989-11-22	Ferrosan As	Heterocykliske forbindelser, deres fremstilling og anvendelse
KR100207360B1 (ko) *	1991-06-14	1999-07-15	돈 더블유. 슈미츠	이미다조[1,5,-a]퀸옥살린
AU4035893A (en) *	1991-12-17	1993-07-19	Upjohn Company, The	3-substituted imidazo (1,5-a) and imidazo (1,5-a)-triazolo (1,5-c) quinoxalines and quinazolines with cns activity
DE4228095A1 (de) *	1992-08-24	1994-03-03	Asta Medica Ag	Neue 4,5-Dihydro-4-oxo-pyrrolo[1,2-a]chinoxaline und entsprechende Aza-analoga und Verfahren zu deren Herstellung
FR2696466B1 (fr) *	1992-10-02	1994-11-25	Rhone Poulenc Rorer Sa	Dérivés de 5H,10H-imidazo[1,2-a]indeno[1,2-e]pyrazine-4-one, leur préparation et les médicaments les contenant.
US5792766A (en)	1996-03-13	1998-08-11	Neurogen Corporation	Imidazo 1,5-c! quinazolines; a new class of GABA brain receptor ligands
JP4042925B2 (ja) *	1996-11-20	2008-02-06	シスメックス株式会社	幼若白血球の分類計数法
US20040180898A1 (en) *	2003-03-03	2004-09-16	Bang-Chi Chen	Processes for preparing imidazoquinoxalinones, heterocyclic-substituted imidazopyrazinones, imidazoquinoxalines and heterocyclic-substituted imidazopyrazines
CN108473495B (zh)	2015-11-20	2022-04-12	福马治疗有限公司	作为泛素-特异性蛋白酶1抑制剂的嘌呤酮

Family Cites Families (6)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4440929A (en) *	1981-07-16	1984-04-03	Usv Pharmaceutical Corporation	Imidazoquinoxaline compounds
DK476885D0 (da) *	1985-10-17	1985-10-17	Ferrosan As	Heterocycliske forbindelser og fremgangsmaader til fremstilling heraf
ATE44381T1 (de) *	1985-10-17	1989-07-15	Ferrosan As	Heterocyclische verbindungen und ihre herstellung und verwendung.
DK155524C (da) *	1987-03-18	1989-09-11	Ferrosan As	Kondenserede imidazolderivater og farmaceutiske praeparater indeholdende disse
DK160876C (da) *	1987-12-08	1991-10-14	Novo Nordisk As	Imidazoquinoxalinforbindelser, fremgangsmaade til deres fremstilling, anvendelse af forbindelserne og farmaceutiske praeparater, hvori forbindelserne indgaar
IL90315A0 (en) *	1988-06-01	1989-12-15	Ferrosan As	Imidazoquinoxaline compounds,their preparation and pharmaceutical compositions containing them

1988
- 1988-11-10 DK DK626288A patent/DK626288D0/da not_active Application Discontinuation
1989
- 1989-10-19 IL IL9205589A patent/IL92055A/en not_active IP Right Cessation
- 1989-10-20 IE IE337489A patent/IE68939B1/en not_active IP Right Cessation
- 1989-10-24 ZA ZA898051A patent/ZA898051B/xx unknown
- 1989-11-03 AU AU44393/89A patent/AU622941B2/en not_active Ceased
- 1989-11-06 FI FI895257A patent/FI92931C/fi not_active IP Right Cessation
- 1989-11-07 JP JP1288081A patent/JPH02178285A/ja active Pending
- 1989-11-08 NZ NZ231321A patent/NZ231321A/xx unknown
- 1989-11-08 US US07/433,668 patent/US4999353A/en not_active Expired - Fee Related
- 1989-11-09 CA CA002002624A patent/CA2002624A1/en not_active Abandoned
- 1989-11-09 ES ES89311587T patent/ES2068903T3/es not_active Expired - Lifetime
- 1989-11-09 EP EP89311587A patent/EP0368652B1/de not_active Expired - Lifetime
- 1989-11-09 NO NO894474A patent/NO173827C/no unknown
- 1989-11-09 AT AT89311587T patent/ATE119162T1/de not_active IP Right Cessation
- 1989-11-09 DE DE68921418T patent/DE68921418T2/de not_active Expired - Fee Related
- 1989-11-10 PT PT92279A patent/PT92279B/pt not_active IP Right Cessation
1995
- 1995-04-10 GR GR950400849T patent/GR3015718T3/el unknown

Also Published As

Publication number	Publication date
US4999353A (en)	1991-03-12
CA2002624A1 (en)	1990-05-10
PT92279B (pt)	1995-08-09
NO173827B (no)	1993-11-01
DE68921418T2 (de)	1995-07-13
JPH02178285A (ja)	1990-07-11
FI895257A0 (fi)	1989-11-06
NO173827C (no)	1994-02-09
EP0368652B1 (de)	1995-03-01
IL92055A0 (en)	1990-07-12
PT92279A (pt)	1990-05-31
AU622941B2 (en)	1992-04-30
DK626288D0 (da)	1988-11-10
ATE119162T1 (de)	1995-03-15
DE68921418D1 (de)	1995-04-06
EP0368652A1 (de)	1990-05-16
ES2068903T3 (es)	1995-05-01
IE893374L (en)	1990-05-10
IE68939B1 (en)	1996-07-24
ZA898051B (en)	1990-08-29
NO894474D0 (no)	1989-11-09
AU4439389A (en)	1990-05-17
NZ231321A (en)	1991-10-25
FI92931B (fi)	1994-10-14
NO894474L (no)	1990-05-11
FI92931C (fi)	1995-01-25
GR3015718T3 (en)	1995-07-31

Legal Events

Date	Code	Title	Description
2000-12-06	RH	Patent void

Publication	Publication Date	Title
US6124285A (en)	2000-09-26	Indole-2,3-dione-3-oxime derivatives
EP0503349B1 (de)	1995-01-04	Hydrazonderivate, ihre Herstellung und Verwendung
SK150398A3 (en)	1999-03-12	Indole derivatives useful as endothelin receptor antagonists
US6177569B1 (en)	2001-01-23	Oxo-pyridoimidazole-carboxamides: GABA brain receptor ligands
EP0362695A1 (de)	1990-04-11	Pyrrolocarbazol-Derivate, Verfahren zu deren Herstellung und deren Verwendung als Arzneimittel
IL92055A (en)	1994-01-25	3-(cycloalkyl substituted 1,2,4-oxadiazolyl)-4,5-dihydro-4-oxo-5- tertbutyl-imidaz (1,5-a) quinoxalines
US6448259B1 (en)	2002-09-10	Substituted cycloalkyl-4-oxonicotinic carboxamides; GABA brain receptor ligands
JPH07103122B2 (ja)	1995-11-08	イミダゾ〔１，２−ｃ〕キナゾリン誘導体、これらの製造方法、及びそれらを含む狭心症薬
JP7198387B2 (ja)	2022-12-28	ピラジン－２（１ｈ）－オン系化合物のｃ結晶形とｅ結晶形及びその製造方法
DE69019920T2 (de)	1995-11-16	Benzocycloalkylaminopyridinamine und verwandte Verbindungen, Verfahren zu ihrer Herstellung, Zwischenverbindungen und ihre Verwendung als Arzneimittel.
JP7200437B2 (ja)	2023-01-06	ピラジン－２（１ｈ）－ケトン系化合物の結晶形ｄ及びその製造方法
JP7198388B2 (ja)	2022-12-28	ピラジン－２（１ｈ）－ケトン化合物の結晶形ａ及び結晶形ｂ及びその製造方法
US5726175A (en)	1998-03-10	Imidazo 1,2-A!indeno 1,2-E!pyrazine-2-carboxylic acid derivatives, preparation thereof and drugs containing same
FI84477C (fi)	1991-12-10	Foerfarande foer framstaellning av farmakologiskt vaerdefulla diazin-etenylfenyloxamsyror.
EP0239667B1 (de)	1991-05-02	5- oder 6-substituierte-beta-carbolin-3-carbonsäureester
JPH01287070A (ja)	1989-11-17	新規の１―アリールスルホニル―２―ピロリジノン誘導体、それらの製造方法及び得られる新規の中間体、それらの薬剤としての使用並びにそれらを含有する組成物
US3575976A (en)	1971-04-20	3-amino-1,2,8,9-tetraazaphenalenes
US4666909A (en)	1987-05-19	Bisbenzothiazine, bisbenzodiazine and bisquinoline pharmaceutical compositions and use
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