PH27044A - Antiviral tetrahydroimidazo Ú1-4¾benzodiazepine-2-ones - Google Patents

Antiviral tetrahydroimidazo Ú1-4¾benzodiazepine-2-ones Download PDF

Info

Publication number: PH27044A
Authority: PH; Philippines
Prior art keywords: hydrogen; galkyl; parts; methyl; compound
Prior art date: 1988-03-18

Application number

PH38339A

Other languages

English (en)

Inventor

Alfons H M Raeymaekers

Josephus L H Van Gelder

Paul A J Janssen

Michael J Kukla

Henry J Breslin

Original Assignee

Janssen Pharmaceutica Nv

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.)

1988-03-18

Filing date

1989-03-17

Publication date

1993-02-01

1989-03-17 Application filed by Janssen Pharmaceutica Nv filed Critical Janssen Pharmaceutica Nv

1993-02-01 Publication of PH27044A publication Critical patent/PH27044A/en

Links

230000000840 anti-viral effect Effects 0.000 title claims abstract description 17
150000001875 compounds Chemical class 0.000 claims abstract description 58
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 46
239000001257 hydrogen Substances 0.000 claims abstract description 43
239000000203 mixture Substances 0.000 claims abstract description 41
238000000034 method Methods 0.000 claims abstract description 21
150000002431 hydrogen Chemical class 0.000 claims abstract description 17
239000002253 acid Substances 0.000 claims abstract description 15
150000003839 salts Chemical class 0.000 claims abstract description 15
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 13
239000004480 active ingredient Substances 0.000 claims abstract description 6
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 3
125000001475 halogen functional group Chemical group 0.000 claims abstract 2
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 14
125000004356 hydroxy functional group Chemical group O* 0.000 claims description 13
125000004093 cyano group Chemical group *C#N 0.000 claims description 9
241001465754 Metazoa Species 0.000 claims description 7
201000010099 disease Diseases 0.000 claims description 5
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 5
230000003612 virological effect Effects 0.000 claims description 5
239000003937 drug carrier Substances 0.000 claims description 4
125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 2
RAXXELZNTBOGNW-UHFFFAOYSA-N 1H-imidazole Chemical compound C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims 1
235000010627 Phaseolus vulgaris Nutrition 0.000 claims 1
244000046052 Phaseolus vulgaris Species 0.000 claims 1
150000004682 monohydrates Chemical class 0.000 claims 1
125000004368 propenyl group Chemical group C(=CC)* 0.000 claims 1
125000003118 aryl group Chemical group 0.000 abstract description 5
239000008194 pharmaceutical composition Substances 0.000 abstract description 5
125000004169 (C1-C6) alkyl group Chemical group 0.000 abstract 5
125000004916 (C1-C6) alkylcarbonyl group Chemical group 0.000 abstract 2
125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 abstract 2
125000004209 (C1-C8) alkyl group Chemical group 0.000 abstract 1
OAVWAKSITUQGNK-UHFFFAOYSA-N 3,3a,4,5-tetrahydro-1h-imidazo[4,5-i][1,4]benzodiazepin-2-one Chemical class C1CC2=CN=CC=NC2=C2C1NC(=O)N2 OAVWAKSITUQGNK-UHFFFAOYSA-N 0.000 abstract 1
239000000243 solution Substances 0.000 description 61
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 42
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239000000543 intermediate Substances 0.000 description 39
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 29
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 27
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 21
-1 Cj.galkyloxy Chemical group 0.000 description 20
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125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 17
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125000004432 carbon atom Chemical group C* 0.000 description 5
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239000002184 metal Substances 0.000 description 5
125000000896 monocarboxylic acid group Chemical group 0.000 description 5
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 5
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238000006396 nitration reaction Methods 0.000 description 1
239000012299 nitrogen atmosphere Substances 0.000 description 1
125000004433 nitrogen atom Chemical group N* 0.000 description 1
231100000252 nontoxic Toxicity 0.000 description 1
230000003000 nontoxic effect Effects 0.000 description 1
239000002674 ointment Substances 0.000 description 1
239000006186 oral dosage form Substances 0.000 description 1
229940098462 oral drops Drugs 0.000 description 1
150000007524 organic acids Chemical class 0.000 description 1
235000005985 organic acids Nutrition 0.000 description 1
150000007530 organic bases Chemical class 0.000 description 1
239000003960 organic solvent Substances 0.000 description 1
125000004043 oxo group Chemical group O=* 0.000 description 1
MUMZUERVLWJKNR-UHFFFAOYSA-N oxoplatinum Chemical compound [Pt]=O MUMZUERVLWJKNR-UHFFFAOYSA-N 0.000 description 1
239000003961 penetration enhancing agent Substances 0.000 description 1
125000002255 pentenyl group Chemical group C(=CCCC)* 0.000 description 1
125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
125000005981 pentynyl group Chemical group 0.000 description 1
208000033808 peripheral neuropathy Diseases 0.000 description 1
230000000144 pharmacologic effect Effects 0.000 description 1
229910003446 platinum oxide Inorganic materials 0.000 description 1
229940068918 polyethylene glycol 400 Drugs 0.000 description 1
239000001267 polyvinylpyrrolidone Substances 0.000 description 1
229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
235000019260 propionic acid Nutrition 0.000 description 1
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
238000000746 purification Methods 0.000 description 1
HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 description 1
230000035484 reaction time Effects 0.000 description 1
238000007363 ring formation reaction Methods 0.000 description 1
229930195734 saturated hydrocarbon Natural products 0.000 description 1
125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
230000001624 sedative effect Effects 0.000 description 1
238000000926 separation method Methods 0.000 description 1
239000000741 silica gel Substances 0.000 description 1
229910002027 silica gel Inorganic materials 0.000 description 1
239000012279 sodium borohydride Substances 0.000 description 1
229910000033 sodium borohydride Inorganic materials 0.000 description 1
BEOOHQFXGBMRKU-UHFFFAOYSA-N sodium cyanoborohydride Chemical compound [Na+].[B-]C#N BEOOHQFXGBMRKU-UHFFFAOYSA-N 0.000 description 1
235000019333 sodium laurylsulphate Nutrition 0.000 description 1
239000000600 sorbitol Substances 0.000 description 1
239000004544 spot-on Substances 0.000 description 1
239000008223 sterile water Substances 0.000 description 1
239000000126 substance Substances 0.000 description 1
235000000346 sugar Nutrition 0.000 description 1
150000008163 sugars Chemical class 0.000 description 1
239000004094 surface-active agent Substances 0.000 description 1
239000000375 suspending agent Substances 0.000 description 1
208000024891 symptom Diseases 0.000 description 1
208000011580 syndromic disease Diseases 0.000 description 1
239000006188 syrup Substances 0.000 description 1
235000020357 syrup Nutrition 0.000 description 1
238000007910 systemic administration Methods 0.000 description 1
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
150000003512 tertiary amines Chemical class 0.000 description 1
RAOIDOHSFRTOEL-UHFFFAOYSA-N tetrahydrothiophene Chemical compound C1CCSC1 RAOIDOHSFRTOEL-UHFFFAOYSA-N 0.000 description 1
230000001225 therapeutic effect Effects 0.000 description 1
206010043554 thrombocytopenia Diseases 0.000 description 1
230000002936 tranquilizing effect Effects 0.000 description 1
150000003626 triacylglycerols Chemical class 0.000 description 1
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
YFNKIDBQEZZDLK-UHFFFAOYSA-N triglyme Chemical compound COCCOCCOCCOC YFNKIDBQEZZDLK-UHFFFAOYSA-N 0.000 description 1
238000003211 trypan blue cell staining Methods 0.000 description 1
230000009385 viral infection Effects 0.000 description 1
235000012431 wafers Nutrition 0.000 description 1
239000000080 wetting agent Substances 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
- C07D487/06—Peri-condensed systems
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/12—Antivirals

Landscapes

Organic Chemistry (AREA)
Chemical & Material Sciences (AREA)
Health & Medical Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Pharmacology & Pharmacy (AREA)
Oncology (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Virology (AREA)
Communicable Diseases (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)
Plural Heterocyclic Compounds (AREA)
Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)

PH38339A 1988-03-18 1989-03-17 Antiviral tetrahydroimidazo Ú1-4¾benzodiazepine-2-ones PH27044A (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
GB888806449A GB8806449D0 (en)	1988-03-18	1988-03-18	Antiviral hexahydroimiazo(1 4)benzodiazepin-2-ones

Publications (1)

Publication Number	Publication Date
PH27044A true PH27044A (en)	1993-02-01

Family

ID=10633662

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
PH38339A PH27044A (en)	1988-03-18	1989-03-17	Antiviral tetrahydroimidazo Ú1-4¾benzodiazepine-2-ones

Country Status (26)

Country	Link
EP (1)	EP0336466B1 (de)
JP (1)	JP2693559B2 (de)
KR (1)	KR0133073B1 (de)
CN (1)	CN1031058C (de)
AT (1)	ATE84035T1 (de)
AU (2)	AU617435B2 (de)
BG (1)	BG51251A3 (de)
CA (1)	CA1310964C (de)
DE (1)	DE68904102T2 (de)
DK (1)	DK130989A (de)
ES (1)	ES2053946T3 (de)
FI (1)	FI89800C (de)
GB (1)	GB8806449D0 (de)
GR (1)	GR3006728T3 (de)
HU (2)	HU203757B (de)
IE (1)	IE63108B1 (de)
IL (1)	IL89633A (de)
JO (1)	JO1589B1 (de)
MY (1)	MY104942A (de)
NO (1)	NO167737C (de)
NZ (1)	NZ228216A (de)
PH (1)	PH27044A (de)
PT (1)	PT90034B (de)
SU (1)	SU1748647A3 (de)
TN (1)	TNSN89039A1 (de)
ZA (1)	ZA892062B (de)

Families Citing this family (16)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US5270464A (en) *	1989-03-14	1993-12-14	Janssen Pharmaceutica N.V.	Anti-HIV-1 tetrahydroimidazo[1,4]benzodiazepin-2-(thi) ones
IL93136A (en) *	1989-02-23	1995-01-24	Janssen Pharmaceutica Nv	Tetrahydroimidazo (1,4) benzodiazepin-2-thione derivatives, their preparation and pharmaceutical compositions containing them
NZ235137A (en) *	1989-09-13	1992-02-25	Janssen Pharmaceutica Nv	Tetrahydroimidazo(1,4)benzodiazepine derivatives, preparation and pharmaceutical compositions thereof
US5164376A (en) *	1989-10-30	1992-11-17	Hoffmann-Laroche Inc.	Method for treating retroviral infections with aryl-(2-pyrryl) keytone compound
EP0436245A1 (de) *	1989-12-27	1991-07-10	Duphar International Research B.V	Substituierte 3,4-annelierte Benzimidazol-2(1H)-one
US5141735A (en) *	1990-06-18	1992-08-25	Hoffman-La Roche, Inc.	Substituted amino-benzodiazepines having anitviral activity
NZ238664A (en) *	1990-07-06	1992-12-23	Janssen Pharmaceutica Nv	Substituted tetrahydroimidazo(1,4)benzodiazepin-2-(thi)ones and pharmaceutical anti-viral compositions
GB9018601D0 (en) *	1990-08-24	1990-10-10	Fujisawa Pharmaceutical Co	Tricyclic compounds
DE4036552C1 (de) *	1990-11-16	1992-02-06	Boehringer Mannheim Gmbh, 6800 Mannheim, De
GB9109557D0 (en)	1991-05-02	1991-06-26	Wellcome Found	Chemical compounds
KR100268694B1 (ko) *	1991-10-11	2000-10-16	미리암 디. 메코너헤이, 블레어큐. 퍼거슨	레트로바이러스 프로테아제 억제제로 유용한 시클릭 우레아 및 유사체
AU4079593A (en) *	1992-05-13	1993-12-13	Wellcome Foundation Limited, The	Therapeutic combinations
US6177435B1 (en)	1992-05-13	2001-01-23	Glaxo Wellcome Inc.	Therapeutic combinations
CA2581025C (en) *	2004-09-22	2011-06-07	Pfizer Inc.	Polymorphic and amorphous forms of the phosphate salt of 8-fluoro-2-{4-[(methylamino)methyl]phenyl}-1,3,4,5-tetrahydro-6h-azepino[5,4,3-cd]indol-6-one
MX2009003916A (es) *	2006-10-13	2009-04-23	Pfizer Ltd	Compuestos heterociclicos utiles como agentes anabolicos para animales de ganado.
CN101827597B (zh)	2007-08-20	2013-03-13	伊沃泰克国际有限责任公司	睡眠障碍的治疗

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
FR2534257A1 (fr) *	1982-10-12	1984-04-13	Roussel Uclaf	Nouveaux derives de la 6-amino 7-hydroxy 4,5,6,7-tetrahydro-imidazo/4,5,1-j-k/ /1/ benzazepin-2(1h)-one, leurs sels, application a titre de medicaments, compositions les renfermant et un intermediaire
IL93136A (en) *	1989-02-23	1995-01-24	Janssen Pharmaceutica Nv	Tetrahydroimidazo (1,4) benzodiazepin-2-thione derivatives, their preparation and pharmaceutical compositions containing them

1988
- 1988-03-18 GB GB888806449A patent/GB8806449D0/en active Pending
1989
- 1989-02-10 MY MYPI89000163A patent/MY104942A/en unknown
- 1989-03-03 NZ NZ228216A patent/NZ228216A/xx unknown
- 1989-03-08 AT AT89200575T patent/ATE84035T1/de not_active IP Right Cessation
- 1989-03-08 EP EP89200575A patent/EP0336466B1/de not_active Expired - Lifetime
- 1989-03-08 ES ES89200575T patent/ES2053946T3/es not_active Expired - Lifetime
- 1989-03-08 DE DE8989200575T patent/DE68904102T2/de not_active Expired - Fee Related
- 1989-03-13 JO JO19891589A patent/JO1589B1/en active
- 1989-03-14 AU AU31310/89A patent/AU617435B2/en not_active Ceased
- 1989-03-14 JP JP1059859A patent/JP2693559B2/ja not_active Expired - Lifetime
- 1989-03-16 BG BG087682A patent/BG51251A3/bg unknown
- 1989-03-16 CA CA000593935A patent/CA1310964C/en not_active Expired - Fee Related
- 1989-03-16 HU HU891240A patent/HU203757B/hu not_active IP Right Cessation
- 1989-03-16 HU HU911782A patent/HU206873B/hu not_active IP Right Cessation
- 1989-03-16 IL IL8963389A patent/IL89633A/en not_active IP Right Cessation
- 1989-03-16 IE IE85189A patent/IE63108B1/en not_active IP Right Cessation
- 1989-03-17 NO NO891176A patent/NO167737C/no unknown
- 1989-03-17 DK DK130989A patent/DK130989A/da not_active Application Discontinuation
- 1989-03-17 PT PT90034A patent/PT90034B/pt not_active IP Right Cessation
- 1989-03-17 SU SU894613664A patent/SU1748647A3/ru active
- 1989-03-17 ZA ZA892062A patent/ZA892062B/xx unknown
- 1989-03-17 PH PH38339A patent/PH27044A/en unknown
- 1989-03-17 FI FI891279A patent/FI89800C/fi not_active IP Right Cessation
- 1989-03-18 CN CN89101474A patent/CN1031058C/zh not_active Expired - Fee Related
- 1989-03-18 KR KR89003388A patent/KR0133073B1/ko not_active Expired - Fee Related
- 1989-03-19 TN TNTNSN89039A patent/TNSN89039A1/fr unknown
1991
- 1991-09-02 AU AU83602/91A patent/AU630575B2/en not_active Ceased
1992
- 1992-12-31 GR GR920403099T patent/GR3006728T3/el unknown

Also Published As

Publication number	Publication date
NZ228216A (en)	1991-01-29
PT90034B (pt)	1994-05-31
NO891176D0 (no)	1989-03-17
JP2693559B2 (ja)	1997-12-24
ES2053946T3 (es)	1994-08-01
FI89800B (fi)	1993-08-13
PT90034A (pt)	1989-11-10
SU1748647A3 (ru)	1992-07-15
DE68904102T2 (de)	1993-05-06
DK130989D0 (da)	1989-03-17
CA1310964C (en)	1992-12-01
EP0336466B1 (de)	1992-12-30
AU3131089A (en)	1989-09-21
IL89633A0 (en)	1989-09-28
IE63108B1 (en)	1995-03-22
NO167737B (no)	1991-08-26
GB8806449D0 (en)	1988-04-20
ATE84035T1 (de)	1993-01-15
HU206873B (en)	1993-01-28
CN1036957A (zh)	1989-11-08
FI891279L (fi)	1989-09-19
AU8360291A (en)	1991-11-07
ZA892062B (en)	1990-11-28
IE890851L (en)	1989-09-18
NO167737C (no)	1991-12-04
CN1031058C (zh)	1996-02-21
AU630575B2 (en)	1992-10-29
FI891279A0 (fi)	1989-03-17
TNSN89039A1 (fr)	1991-02-04
HU203757B (en)	1991-09-30
BG51251A3 (bg)	1993-03-15
HUT52099A (en)	1990-06-28
KR0133073B1 (en)	1998-04-17
AU617435B2 (en)	1991-11-28
JPH01275582A (ja)	1989-11-06
DK130989A (da)	1989-09-19
HU911782D0 (en)	1991-12-30
DE68904102D1 (de)	1993-02-11
EP0336466A1 (de)	1989-10-11
KR890014546A (ko)	1989-10-24
IL89633A (en)	1994-02-27
GR3006728T3 (de)	1993-06-30
JO1589B1 (en)	1989-12-16
FI89800C (fi)	1993-11-25
MY104942A (en)	1994-07-30
NO891176L (no)	1989-09-19

Publication	Publication Date	Title
EP0336466B1 (de)	1992-12-30	Antivirale Tetrahydroimidazo(1,4)benzodiazepin-2-one
EP0384522B1 (de)	1993-01-13	Antivirale Tetrahydroimidazo[1,4]benzodiazepin-2-thione
US6201119B1 (en)	2001-03-13	Antiretroviral tetrahydroimidazo[1,4]benzodiazepin-2(thi) ones
EP0538297B9 (de)	2002-10-16	Antivirale tetrahydroimidazo[1,4]benzodiazepin-2-(thio)one
AU635328B2 (en)	1993-03-18	Antiviral tetrahydroimidazo (1,4) benzodiazepines
HU207322B (en)	1993-03-29	Process for producing imidazo-benzodiazepin-2/1h/-one derivatives and pharmaceutical compositions containing them
HRP930480A2 (en)	1996-02-29	Antiviral tetrahydroimidazo (1,4) benzodiazepine-2-thiones