NO300328B1 - Fremstilling av antivirale tetrahydroimidazo£1,4|benzodiazepiner - Google Patents
Fremstilling av antivirale tetrahydroimidazo£1,4|benzodiazepiner Download PDFInfo
- Publication number
- NO300328B1 NO300328B1 NO920505A NO920505A NO300328B1 NO 300328 B1 NO300328 B1 NO 300328B1 NO 920505 A NO920505 A NO 920505A NO 920505 A NO920505 A NO 920505A NO 300328 B1 NO300328 B1 NO 300328B1
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- parts
- formula
- alkyl
- reaction
- hydrogen
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- 238000002360 preparation method Methods 0.000 title claims description 18
- 230000000840 anti-viral effect Effects 0.000 title claims description 11
- 229940049706 benzodiazepine Drugs 0.000 title description 3
- 150000001557 benzodiazepines Chemical class 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims description 41
- 229910052739 hydrogen Inorganic materials 0.000 claims description 27
- 239000001257 hydrogen Substances 0.000 claims description 26
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 22
- 238000000034 method Methods 0.000 claims description 21
- 125000000217 alkyl group Chemical group 0.000 claims description 16
- 239000002253 acid Substances 0.000 claims description 15
- 150000003839 salts Chemical class 0.000 claims description 14
- 239000012442 inert solvent Substances 0.000 claims description 7
- XOMOXQVMQKLWHB-UHFFFAOYSA-N 1,2,3,3a-tetrahydroimidazo[4,5-i][1,4]benzodiazepine Chemical class C1=CC2=CN=CC=NC2=C2C1NCN2 XOMOXQVMQKLWHB-UHFFFAOYSA-N 0.000 claims description 4
- 238000009833 condensation Methods 0.000 claims description 4
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- 230000008569 process Effects 0.000 claims description 2
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 1
- LZMOFROOIHNXKL-UHFFFAOYSA-N 2,3,4,5-tetrahydro-1h-1,4-benzodiazepin-9-amine Chemical compound C1NCCNC2=C1C=CC=C2N LZMOFROOIHNXKL-UHFFFAOYSA-N 0.000 claims 1
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- PVWOIHVRPOBWPI-UHFFFAOYSA-N n-propyl iodide Chemical compound CCCI PVWOIHVRPOBWPI-UHFFFAOYSA-N 0.000 description 1
- 150000002823 nitrates Chemical class 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 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
- 239000003961 penetration enhancing agent Substances 0.000 description 1
- 125000002255 pentenyl 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
- DGTNSSLYPYDJGL-UHFFFAOYSA-N phenyl isocyanate Chemical compound O=C=NC1=CC=CC=C1 DGTNSSLYPYDJGL-UHFFFAOYSA-N 0.000 description 1
- 229940117953 phenylisothiocyanate Drugs 0.000 description 1
- OJMIONKXNSYLSR-UHFFFAOYSA-N phosphorous acid Chemical compound OP(O)O OJMIONKXNSYLSR-UHFFFAOYSA-N 0.000 description 1
- FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 description 1
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 1
- 239000002574 poison Substances 0.000 description 1
- 231100000614 poison Toxicity 0.000 description 1
- 229940068918 polyethylene glycol 400 Drugs 0.000 description 1
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 125000001844 prenyl group Chemical group [H]C([*])([H])C([H])=C(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- 239000001294 propane Substances 0.000 description 1
- AOHJOMMDDJHIJH-UHFFFAOYSA-N propylenediamine Chemical compound CC(N)CN AOHJOMMDDJHIJH-UHFFFAOYSA-N 0.000 description 1
- BOLDJAUMGUJJKM-LSDHHAIUSA-N renifolin D Natural products CC(=C)[C@@H]1Cc2c(O)c(O)ccc2[C@H]1CC(=O)c3ccc(O)cc3O BOLDJAUMGUJJKM-LSDHHAIUSA-N 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
- 230000035945 sensitivity Effects 0.000 description 1
- 235000011803 sesame oil Nutrition 0.000 description 1
- 239000008159 sesame oil Substances 0.000 description 1
- 239000012419 sodium bis(2-methoxyethoxy)aluminum hydride Substances 0.000 description 1
- 239000012279 sodium borohydride Substances 0.000 description 1
- 229910000033 sodium borohydride Inorganic materials 0.000 description 1
- JVBXVOWTABLYPX-UHFFFAOYSA-L sodium dithionite Chemical compound [Na+].[Na+].[O-]S(=O)S([O-])=O JVBXVOWTABLYPX-UHFFFAOYSA-L 0.000 description 1
- GRVFOGOEDUUMBP-UHFFFAOYSA-N sodium sulfide (anhydrous) Chemical compound [Na+].[Na+].[S-2] GRVFOGOEDUUMBP-UHFFFAOYSA-N 0.000 description 1
- UNHKSXOTUHOTAB-UHFFFAOYSA-N sodium;sulfane Chemical compound [Na].S UNHKSXOTUHOTAB-UHFFFAOYSA-N 0.000 description 1
- 238000000638 solvent extraction Methods 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 238000010025 steaming Methods 0.000 description 1
- 239000008223 sterile water Substances 0.000 description 1
- 239000012258 stirred mixture Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 235000000346 sugar Nutrition 0.000 description 1
- 150000008163 sugars Chemical class 0.000 description 1
- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 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
- 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
- 230000001225 therapeutic effect Effects 0.000 description 1
- 229930192474 thiophene Natural products 0.000 description 1
- 206010043554 thrombocytopenia Diseases 0.000 description 1
- YONPGGFAJWQGJC-UHFFFAOYSA-K titanium(iii) chloride Chemical compound Cl[Ti](Cl)Cl YONPGGFAJWQGJC-UHFFFAOYSA-K 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
- 150000003626 triacylglycerols Chemical class 0.000 description 1
- YFNKIDBQEZZDLK-UHFFFAOYSA-N triglyme Chemical compound COCCOCCOCCOC YFNKIDBQEZZDLK-UHFFFAOYSA-N 0.000 description 1
- 230000035899 viability Effects 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/02—Immunomodulators
- A61P37/04—Immunostimulants
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Immunology (AREA)
- Veterinary Medicine (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Oncology (AREA)
- Communicable Diseases (AREA)
- Virology (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US40662589A | 1989-09-13 | 1989-09-13 | |
PCT/EP1990/001546 WO1991004255A1 (en) | 1989-09-13 | 1990-09-06 | Antiviral tetrahydroimidazo[1,4]benzodiazepines |
Publications (3)
Publication Number | Publication Date |
---|---|
NO920505D0 NO920505D0 (no) | 1992-02-07 |
NO920505L NO920505L (no) | 1992-02-07 |
NO300328B1 true NO300328B1 (no) | 1997-05-12 |
Family
ID=23608794
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
NO920505A NO300328B1 (no) | 1989-09-13 | 1992-02-07 | Fremstilling av antivirale tetrahydroimidazo£1,4|benzodiazepiner |
Country Status (30)
Country | Link |
---|---|
EP (2) | EP0491751A1 (el) |
JP (1) | JPH05500053A (el) |
KR (1) | KR927003596A (el) |
CN (1) | CN1029971C (el) |
AP (1) | AP174A (el) |
AT (1) | ATE115144T1 (el) |
AU (1) | AU635328B2 (el) |
BG (1) | BG60681B1 (el) |
CA (1) | CA2064782A1 (el) |
DE (1) | DE69014784T2 (el) |
DK (1) | DK0417840T3 (el) |
ES (1) | ES2067652T3 (el) |
FI (1) | FI98816C (el) |
GR (1) | GR3015270T3 (el) |
HU (1) | HUT62297A (el) |
IE (1) | IE65357B1 (el) |
IL (3) | IL108074A (el) |
MA (1) | MA21948A1 (el) |
MY (1) | MY106961A (el) |
NO (1) | NO300328B1 (el) |
NZ (1) | NZ235137A (el) |
OA (1) | OA09565A (el) |
PT (1) | PT95303B (el) |
RO (1) | RO109199B1 (el) |
RU (1) | RU2099341C1 (el) |
TN (1) | TNSN90121A1 (el) |
TW (1) | TW199160B (el) |
WO (1) | WO1991004255A1 (el) |
YU (1) | YU169090A (el) |
ZA (1) | ZA907278B (el) |
Families Citing this family (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
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 |
EP0475231A1 (en) * | 1990-09-10 | 1992-03-18 | F. Hoffmann-La Roche Ag | Benzodiazepines |
Family Cites Families (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4075206A (en) * | 1977-02-25 | 1978-02-21 | Eli Lilly And Company | Substituted pyrroloquinoxalinones and diones |
GB8806449D0 (en) * | 1988-03-18 | 1988-04-20 | Janssen Pharmaceutica Nv | Antiviral hexahydroimiazo(1 4)benzodiazepin-2-ones |
IL93136A (en) * | 1989-02-23 | 1995-01-24 | Janssen Pharmaceutica Nv | History of tetrahydroimidazo [1,4] benzodiazepine-2-thione, their preparation and pharmaceutical preparations containing them |
-
1990
- 1990-08-31 NZ NZ235137A patent/NZ235137A/en unknown
- 1990-09-05 YU YU169090A patent/YU169090A/sh unknown
- 1990-09-06 DE DE69014784T patent/DE69014784T2/de not_active Expired - Lifetime
- 1990-09-06 HU HU92816A patent/HUT62297A/hu unknown
- 1990-09-06 AT AT90202369T patent/ATE115144T1/de not_active IP Right Cessation
- 1990-09-06 KR KR1019920700394A patent/KR927003596A/ko not_active Application Discontinuation
- 1990-09-06 JP JP2512169A patent/JPH05500053A/ja active Pending
- 1990-09-06 DK DK90202369.6T patent/DK0417840T3/da active
- 1990-09-06 EP EP90913194A patent/EP0491751A1/en active Pending
- 1990-09-06 RU SU925011526A patent/RU2099341C1/ru active
- 1990-09-06 EP EP90202369A patent/EP0417840B1/en not_active Expired - Lifetime
- 1990-09-06 AU AU62934/90A patent/AU635328B2/en not_active Ceased
- 1990-09-06 RO RO92-200221A patent/RO109199B1/ro unknown
- 1990-09-06 ES ES90202369T patent/ES2067652T3/es not_active Expired - Lifetime
- 1990-09-06 WO PCT/EP1990/001546 patent/WO1991004255A1/en active IP Right Grant
- 1990-09-06 CA CA002064782A patent/CA2064782A1/en not_active Abandoned
- 1990-09-10 MA MA22220A patent/MA21948A1/fr unknown
- 1990-09-11 MY MYPI90001567A patent/MY106961A/en unknown
- 1990-09-11 IL IL10807490A patent/IL108074A/en not_active IP Right Cessation
- 1990-09-11 AP APAP/P/1990/000205A patent/AP174A/en active
- 1990-09-11 IL IL9563890A patent/IL95638A/en not_active IP Right Cessation
- 1990-09-12 ZA ZA907278A patent/ZA907278B/xx unknown
- 1990-09-12 IE IE331390A patent/IE65357B1/en not_active IP Right Cessation
- 1990-09-13 TN TNTNSN90121A patent/TNSN90121A1/fr unknown
- 1990-09-13 PT PT95303A patent/PT95303B/pt not_active IP Right Cessation
- 1990-09-13 CN CN90107656A patent/CN1029971C/zh not_active Expired - Fee Related
- 1990-10-08 TW TW079108420A patent/TW199160B/zh active
-
1992
- 1992-02-07 NO NO920505A patent/NO300328B1/no unknown
- 1992-03-12 BG BG96041A patent/BG60681B1/bg unknown
- 1992-03-12 FI FI921070A patent/FI98816C/fi not_active IP Right Cessation
- 1992-03-13 OA OA60163A patent/OA09565A/fr unknown
-
1993
- 1993-12-17 IL IL10807493A patent/IL108074A0/xx unknown
-
1995
- 1995-03-03 GR GR940403886T patent/GR3015270T3/el unknown
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