FI75568C - Foerfarande foer framstaellning av terapeutiskt anvaendbara imidazo/1,2-a/kinolinderivat. - Google Patents
Foerfarande foer framstaellning av terapeutiskt anvaendbara imidazo/1,2-a/kinolinderivat. Download PDFInfo
- Publication number
- FI75568C FI75568C FI821171A FI821171A FI75568C FI 75568 C FI75568 C FI 75568C FI 821171 A FI821171 A FI 821171A FI 821171 A FI821171 A FI 821171A FI 75568 C FI75568 C FI 75568C
- Authority
- FI
- Finland
- Prior art keywords
- radical
- formula
- alkoxy
- alkyl
- group
- Prior art date
Links
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 10
- 238000002360 preparation method Methods 0.000 claims abstract description 9
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 7
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims abstract description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 4
- 239000001257 hydrogen Substances 0.000 claims abstract description 4
- 150000001875 compounds Chemical class 0.000 claims description 39
- -1 alkyl radical Chemical class 0.000 claims description 22
- 125000005843 halogen group Chemical group 0.000 claims description 8
- 238000000034 method Methods 0.000 claims description 8
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims description 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
- 229940027991 antiseptic and disinfectant quinoline derivative Drugs 0.000 claims description 3
- KHUXNRRPPZOJPT-UHFFFAOYSA-N phenoxy radical Chemical compound O=C1C=C[CH]C=C1 KHUXNRRPPZOJPT-UHFFFAOYSA-N 0.000 claims description 3
- 208000019901 Anxiety disease Diseases 0.000 claims description 2
- 150000001450 anions Chemical class 0.000 claims description 2
- 230000036506 anxiety Effects 0.000 claims description 2
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 1
- 239000002253 acid Substances 0.000 abstract description 8
- 150000003839 salts Chemical class 0.000 abstract description 8
- 230000000147 hypnotic effect Effects 0.000 abstract description 4
- 125000004435 hydrogen atom Chemical class [H]* 0.000 abstract description 3
- HJMONQQZFQKQPS-UHFFFAOYSA-N imidazo[1,2-a]quinoline Chemical class C1=CC=C2N3C=CN=C3C=CC2=C1 HJMONQQZFQKQPS-UHFFFAOYSA-N 0.000 abstract description 3
- 230000000949 anxiolytic effect Effects 0.000 abstract description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract description 2
- 125000004432 carbon atom Chemical group C* 0.000 abstract 5
- 229910052736 halogen Inorganic materials 0.000 abstract 2
- 150000002367 halogens Chemical class 0.000 abstract 2
- 125000004414 alkyl thio group Chemical group 0.000 abstract 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 abstract 1
- 231100000252 nontoxic Toxicity 0.000 abstract 1
- 230000003000 nontoxic effect Effects 0.000 abstract 1
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 abstract 1
- 125000004076 pyridyl group Chemical group 0.000 abstract 1
- 125000001544 thienyl group Chemical group 0.000 abstract 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 8
- 208000002193 Pain Diseases 0.000 description 5
- 239000004480 active ingredient Substances 0.000 description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 230000000144 pharmacologic effect Effects 0.000 description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
- 229910052801 chlorine Inorganic materials 0.000 description 3
- 239000000460 chlorine Substances 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 239000003960 organic solvent Substances 0.000 description 3
- 239000011800 void material Substances 0.000 description 3
- ATAQGXABHTXTDL-UHFFFAOYSA-N (7-ethyl-5-methoxyimidazo[1,2-a]quinolin-2-yl)-phenylmethanone Chemical compound C=1C(CC)=CC=C(N2C=3)C=1C(OC)=CC2=NC=3C(=O)C1=CC=CC=C1 ATAQGXABHTXTDL-UHFFFAOYSA-N 0.000 description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- 241001465754 Metazoa Species 0.000 description 2
- 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 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- NKDDWNXOKDWJAK-UHFFFAOYSA-N dimethoxymethane Chemical compound COCOC NKDDWNXOKDWJAK-UHFFFAOYSA-N 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 229960002200 flunitrazepam Drugs 0.000 description 2
- 238000002955 isolation Methods 0.000 description 2
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
- 239000008194 pharmaceutical composition Substances 0.000 description 2
- 239000000546 pharmaceutical excipient Substances 0.000 description 2
- 229910000027 potassium carbonate Inorganic materials 0.000 description 2
- 125000004159 quinolin-2-yl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C([H])C(*)=NC2=C1[H] 0.000 description 2
- 150000003254 radicals Chemical class 0.000 description 2
- 238000007363 ring formation reaction Methods 0.000 description 2
- 230000035939 shock Effects 0.000 description 2
- DVWBHZDUDSRLMY-UHFFFAOYSA-N (5-methylsulfanylimidazo[1,2-a]quinolin-2-yl)-phenylmethanone Chemical compound C=1N2C3=CC=CC=C3C(SC)=CC2=NC=1C(=O)C1=CC=CC=C1 DVWBHZDUDSRLMY-UHFFFAOYSA-N 0.000 description 1
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 description 1
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 description 1
- HKPUZZOQHBYMPZ-UHFFFAOYSA-N 1-$l^{1}-sulfanylpropane Chemical compound CCC[S] HKPUZZOQHBYMPZ-UHFFFAOYSA-N 0.000 description 1
- XNHDJBJSICAZMR-UHFFFAOYSA-N 3-bromo-1-phenylpropane-1,2-dione Chemical compound BrCC(=O)C(=O)C1=CC=CC=C1 XNHDJBJSICAZMR-UHFFFAOYSA-N 0.000 description 1
- OXMIRQCGKPEOFA-UHFFFAOYSA-N 6-ethyl-4-methoxyquinolin-2-amine Chemical compound N1=C(N)C=C(OC)C2=CC(CC)=CC=C21 OXMIRQCGKPEOFA-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 208000000094 Chronic Pain Diseases 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- 102000004300 GABA-A Receptors Human genes 0.000 description 1
- 108090000839 GABA-A Receptors Proteins 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 1
- 206010022998 Irritability Diseases 0.000 description 1
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 1
- 240000007472 Leucaena leucocephala Species 0.000 description 1
- 235000010643 Leucaena leucocephala Nutrition 0.000 description 1
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 1
- 206010049816 Muscle tightness Diseases 0.000 description 1
- 208000001431 Psychomotor Agitation Diseases 0.000 description 1
- 206010038743 Restlessness Diseases 0.000 description 1
- 208000013738 Sleep Initiation and Maintenance disease Diseases 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 125000002252 acyl group Chemical group 0.000 description 1
- 230000016571 aggressive behavior Effects 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 230000000202 analgesic effect Effects 0.000 description 1
- 230000003266 anti-allergic effect Effects 0.000 description 1
- 239000002249 anxiolytic agent Substances 0.000 description 1
- 229940005530 anxiolytics Drugs 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 230000027455 binding Effects 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 238000009835 boiling Methods 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
- 239000002775 capsule Substances 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 229940110456 cocoa butter Drugs 0.000 description 1
- 235000019868 cocoa butter Nutrition 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 239000002552 dosage form Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 239000003937 drug carrier Substances 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 239000012458 free base Substances 0.000 description 1
- 150000002334 glycols Chemical class 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000003326 hypnotic agent Substances 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 206010022437 insomnia Diseases 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- WCYWZMWISLQXQU-UHFFFAOYSA-N methyl Chemical group [CH3] WCYWZMWISLQXQU-UHFFFAOYSA-N 0.000 description 1
- GRVDJDISBSALJP-UHFFFAOYSA-N methyloxidanyl Chemical compound [O]C GRVDJDISBSALJP-UHFFFAOYSA-N 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 210000004129 prosencephalon Anatomy 0.000 description 1
- 239000002287 radioligand Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 230000009870 specific binding Effects 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 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
- 235000013311 vegetables Nutrition 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms 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
- C07D215/38—Nitrogen atoms
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Neurosurgery (AREA)
- Life Sciences & Earth Sciences (AREA)
- Neurology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Anesthesiology (AREA)
- Pharmacology & Pharmacy (AREA)
- Biomedical Technology (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)
- Sorption Type Refrigeration Machines (AREA)
- Soil Conditioners And Soil-Stabilizing Materials (AREA)
- Curing Cements, Concrete, And Artificial Stone (AREA)
- Adhesives Or Adhesive Processes (AREA)
- Medicines Containing Antibodies Or Antigens For Use As Internal Diagnostic Agents (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB8110586 | 1981-04-03 | ||
| GB8110586 | 1981-04-03 |
Publications (4)
| Publication Number | Publication Date |
|---|---|
| FI821171A0 FI821171A0 (fi) | 1982-04-02 |
| FI821171L FI821171L (fi) | 1982-10-04 |
| FI75568B FI75568B (fi) | 1988-03-31 |
| FI75568C true FI75568C (fi) | 1988-07-11 |
Family
ID=10520927
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FI821171A FI75568C (fi) | 1981-04-03 | 1982-04-02 | Foerfarande foer framstaellning av terapeutiskt anvaendbara imidazo/1,2-a/kinolinderivat. |
Country Status (24)
| Country | Link |
|---|---|
| US (1) | US4387098A (en, 2012) |
| EP (1) | EP0062580B1 (en, 2012) |
| JP (1) | JPS57176986A (en, 2012) |
| KR (1) | KR880001738B1 (en, 2012) |
| AT (1) | ATE16389T1 (en, 2012) |
| AU (1) | AU554856B2 (en, 2012) |
| CA (1) | CA1175428A (en, 2012) |
| DE (1) | DE3267238D1 (en, 2012) |
| DK (1) | DK156572C (en, 2012) |
| EG (1) | EG15805A (en, 2012) |
| ES (1) | ES510483A0 (en, 2012) |
| FI (1) | FI75568C (en, 2012) |
| GB (1) | GB2096143B (en, 2012) |
| GR (1) | GR76063B (en, 2012) |
| HU (1) | HU189129B (en, 2012) |
| IE (1) | IE52873B1 (en, 2012) |
| IL (1) | IL65140A (en, 2012) |
| MA (1) | MA19434A1 (en, 2012) |
| MX (1) | MX7118E (en, 2012) |
| NO (1) | NO157578C (en, 2012) |
| NZ (1) | NZ200218A (en, 2012) |
| PH (1) | PH17858A (en, 2012) |
| PT (1) | PT74699B (en, 2012) |
| ZA (1) | ZA821407B (en, 2012) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ZA836701B (en) * | 1982-10-01 | 1984-10-31 | Roussel Uclaf | Imidazo(1,2-a)quinolines |
| US4675323A (en) * | 1985-08-06 | 1987-06-23 | Synthelabo | Imidazo(1,2-a)quinoline derivatives useful as anxiolytic agents |
| GB8620060D0 (en) * | 1986-08-18 | 1986-10-01 | Roussel Lab Ltd | Chemical compounds |
| FR2624861B1 (fr) * | 1987-12-21 | 1990-06-01 | Delalande Sa | Carbamates tricycliques, leur procede de preparation et leur application en therapeutique |
| HUP0105406A3 (en) * | 2001-12-21 | 2003-12-29 | Sanofi Aventis | Imidazo[1,2-a]quinolin derivatives, process for their preparation, pharmaceutical compositions thereof and intermediates |
| HUP0700395A2 (en) * | 2007-06-07 | 2009-03-02 | Sanofi Aventis | Substituted [1,2,4] triazolo [1,5-a] quinolines, process for their preparation, pharmaceutical compositions thereof, and intermediates |
| BR112023001551A2 (pt) * | 2020-08-17 | 2023-02-28 | Lmito Therapeutics Inc | Composto de imidazoquinolina ou benzoindazolona e intermediário para preparar o mesmo |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1596652A (en) * | 1977-01-20 | 1981-08-26 | Roussel Lab Ltd | Imidazo (1,2-a) quinoline-2-carboxylic acid and derivatives |
-
1981
- 1981-03-31 GR GR67771A patent/GR76063B/el unknown
-
1982
- 1982-03-01 IL IL65140A patent/IL65140A/xx unknown
- 1982-03-03 ZA ZA821407A patent/ZA821407B/xx unknown
- 1982-03-16 ES ES510483A patent/ES510483A0/es active Granted
- 1982-03-22 KR KR8201210A patent/KR880001738B1/ko not_active Expired
- 1982-03-25 US US06/361,779 patent/US4387098A/en not_active Expired - Fee Related
- 1982-03-29 PH PH27075A patent/PH17858A/en unknown
- 1982-03-29 EG EG168/82A patent/EG15805A/xx active
- 1982-03-30 MX MX8210010U patent/MX7118E/es unknown
- 1982-03-31 DE DE8282400590T patent/DE3267238D1/de not_active Expired
- 1982-03-31 EP EP82400590A patent/EP0062580B1/fr not_active Expired
- 1982-03-31 CA CA000400184A patent/CA1175428A/en not_active Expired
- 1982-03-31 AT AT82400590T patent/ATE16389T1/de active
- 1982-04-02 PT PT74699A patent/PT74699B/pt unknown
- 1982-04-02 AU AU82314/82A patent/AU554856B2/en not_active Ceased
- 1982-04-02 FI FI821171A patent/FI75568C/fi not_active IP Right Cessation
- 1982-04-02 GB GB8209850A patent/GB2096143B/en not_active Expired
- 1982-04-02 NZ NZ200218A patent/NZ200218A/en unknown
- 1982-04-02 NO NO821118A patent/NO157578C/no unknown
- 1982-04-02 DK DK150782A patent/DK156572C/da not_active IP Right Cessation
- 1982-04-02 IE IE780/82A patent/IE52873B1/en unknown
- 1982-04-02 JP JP57053960A patent/JPS57176986A/ja active Pending
- 1982-04-02 HU HU821022A patent/HU189129B/hu not_active IP Right Cessation
- 1982-04-02 MA MA19638A patent/MA19434A1/fr unknown
Also Published As
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE69315920T2 (de) | Kondensierte heterozyklische Verbindungen, deren Herstellung und Verwendung | |
| Bergman et al. | Studies of rutaecarpine and related quinazolinocarboline alkaloids | |
| US5061795A (en) | Hexa-cyclic compound | |
| WO1993004047A1 (en) | Quinazoline derivatives as inhibitors of hiv reverse transcriptase | |
| DK174161B1 (da) | Anellerede indolderivater, fremgangsmåde til deres fremstilling og fremgangsmåde til fremstilling af farmaceutisk præparat indeholdende dem | |
| TW593280B (en) | CRF antagonistic quino- and quinazolines | |
| JP3255416B2 (ja) | １‐ピペラジノ‐１，２‐ジヒドロインデン誘導体 | |
| DE60016566T2 (de) | Triazolopyridazinderivate als liganden für gaba-rezeptoren | |
| CZ20024229A3 (cs) | Tetrahydropyridino nebo piperidino heterocyklické deriváty | |
| NO154883B (no) | Analogifremgangsmaate ved fremstilling av nye, terapeutisk aktive 2-acylaminomethyl-1,4-benzodiazepiner. | |
| PL175615B1 (pl) | Benzoksazynony będące inhibitorami odwrotnej transkryptazy HIV, zawierające je środki farmaceutyczne oraz sposób wytwarzania (-)-6-chloro-4-cyklopropyloetynylo-4-trifluorometylo-1,4-dihydro-2H-3,1-benzoksazyn-2-onu | |
| JPH09505030A (ja) | ヒドロイソキノリン誘導体 | |
| JPH0412269B2 (en, 2012) | ||
| FI75568B (fi) | Foerfarande foer framstaellning av terapeutiskt anvaendbara imidazo/1,2-a/kinolinderivat. | |
| Perez et al. | A new approach to the synthesis of antitumor benzophenanthridine alkaloids. Formal synthesis of nitidine | |
| HINO et al. | A novel class of antiulcer agents. 4-Phenyl-2-(1-piperazinyl) quinolines | |
| DE68913365T2 (de) | 4-Amino-3-carboxynaphthyridin-Derivate, ihre Herstellung und pharmazeutische Zusammensetzungen. | |
| El-Agrody et al. | Synthesis of certain novel 4H-pyrano [3, 2-h] quinoline derivatives | |
| KR920003065B1 (ko) | 벤조디옥시노피롤 유도체의 제조방법 | |
| WO2006066955A1 (de) | Chinolinderivat, dessen verwendung, herstellung und dieses enthaltendes arzneimittel | |
| WO2015050212A1 (ja) | Ｔ型カルシウムチャネル阻害剤 | |
| CA1099712A (en) | Antihypertensive polyfluorohydroxyisopropyl bicyclic and tricyclic carbostryrils | |
| SK284103B6 (sk) | 3-Substituované deriváty 3H-2,3-benzodiazepínu, spôsob ich výroby, ich použitie v liečivách a farmaceutický prostriedok tieto látky obsahujúci | |
| JP3781698B2 (ja) | 新規ピリミジン−４−オン化合物、その調製方法、およびそれらを含む医薬組成物 | |
| DE2233682A1 (de) | 2- eckige klammer auf 3-(subst. aminomethyl)-4-h-1,2,4-triazol-4-yl eckige klammer zu -benzophenone, ein verfahren zu ihrer herstellung sowie diese enthaltende arzneimittel |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MM | Patent lapsed |
Owner name: ROUSSEL UCLAF SOCIETE ANONYME |