NO864518L - Fremgangsmaate for fremstilling av thiazolo(4,5-c)kinoliner - Google Patents
Fremgangsmaate for fremstilling av thiazolo(4,5-c)kinolinerInfo
- Publication number
- NO864518L NO864518L NO864518A NO864518A NO864518L NO 864518 L NO864518 L NO 864518L NO 864518 A NO864518 A NO 864518A NO 864518 A NO864518 A NO 864518A NO 864518 L NO864518 L NO 864518L
- Authority
- NO
- Norway
- Prior art keywords
- general formula
- quinoline
- thiazolo
- acid addition
- acid
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 27
- 238000002360 preparation method Methods 0.000 title claims description 4
- 229940111121 antirheumatic drug quinolines Drugs 0.000 title 1
- 150000003248 quinolines Chemical class 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims description 36
- 239000002253 acid Substances 0.000 claims description 29
- 150000003839 salts Chemical class 0.000 claims description 28
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 20
- 238000006243 chemical reaction Methods 0.000 claims description 16
- 239000011541 reaction mixture Substances 0.000 claims description 15
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 14
- YJBLTYRYUXKJLE-UHFFFAOYSA-N 3-amino-1h-quinoline-4-thione Chemical compound C1=CC=C2C(=S)C(N)=CNC2=C1 YJBLTYRYUXKJLE-UHFFFAOYSA-N 0.000 claims description 11
- 125000000217 alkyl group Chemical group 0.000 claims description 11
- OWHMGQJEHHCWCJ-UHFFFAOYSA-N [1,3]thiazolo[4,5-c]quinoline Chemical class C1=CC=CC2=C(SC=N3)C3=CN=C21 OWHMGQJEHHCWCJ-UHFFFAOYSA-N 0.000 claims description 9
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 8
- 125000004432 carbon atom Chemical group C* 0.000 claims description 7
- 229910052739 hydrogen Inorganic materials 0.000 claims description 7
- 239000001257 hydrogen Substances 0.000 claims description 7
- 125000003545 alkoxy group Chemical group 0.000 claims description 6
- CCIVGXIOQKPBKL-UHFFFAOYSA-M ethanesulfonate Chemical compound CCS([O-])(=O)=O CCIVGXIOQKPBKL-UHFFFAOYSA-M 0.000 claims description 6
- 239000007858 starting material Substances 0.000 claims description 6
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 5
- 229910052736 halogen Inorganic materials 0.000 claims description 5
- 150000002367 halogens Chemical class 0.000 claims description 5
- 150000008064 anhydrides Chemical class 0.000 claims description 4
- 125000005843 halogen group Chemical group 0.000 claims description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
- 125000001424 substituent group Chemical group 0.000 claims description 4
- 150000002148 esters Chemical class 0.000 claims description 3
- 239000007800 oxidant agent Substances 0.000 claims description 3
- 125000004950 trifluoroalkyl group Chemical group 0.000 claims description 3
- 150000004820 halides Chemical class 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
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- 238000012360 testing method Methods 0.000 description 22
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 21
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- PTPFCOYIENEVQA-UHFFFAOYSA-N [1,3]thiazolo[4,5-c]quinoline;hydrochloride Chemical compound Cl.C1=CC=CC2=C(SC=N3)C3=CN=C21 PTPFCOYIENEVQA-UHFFFAOYSA-N 0.000 description 6
- OSUDJKDDCBAIBJ-UHFFFAOYSA-N ethanesulfonic acid;[1,3]thiazolo[4,5-c]quinoline Chemical compound CCS(O)(=O)=O.C1=CC=CC2=C(SC=N3)C3=CN=C21 OSUDJKDDCBAIBJ-UHFFFAOYSA-N 0.000 description 6
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- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 2
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- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
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- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical group OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 2
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- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 2
- 230000004888 barrier function Effects 0.000 description 2
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- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 2
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- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical compound BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
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- ANTSCNMPPGJYLG-UHFFFAOYSA-N chlordiazepoxide Chemical compound O=N=1CC(NC)=NC2=CC=C(Cl)C=C2C=1C1=CC=CC=C1 ANTSCNMPPGJYLG-UHFFFAOYSA-N 0.000 description 2
- 229960004782 chlordiazepoxide Drugs 0.000 description 2
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- FYWDUUCSIVYZLY-UHFFFAOYSA-N 2-(trifluoromethyl)-[1,3]thiazolo[4,5-c]quinoline Chemical compound C1=CC=CC2=C(SC(C(F)(F)F)=N3)C3=CN=C21 FYWDUUCSIVYZLY-UHFFFAOYSA-N 0.000 description 1
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- 238000002156 mixing Methods 0.000 description 1
- 229960005181 morphine Drugs 0.000 description 1
- KSHSRFOLLXJJGF-UHFFFAOYSA-N n-(7-chloro-4-sulfanylidene-1h-quinolin-3-yl)acetamide Chemical compound C1=C(Cl)C=CC2=C(S)C(NC(=O)C)=CN=C21 KSHSRFOLLXJJGF-UHFFFAOYSA-N 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 239000004081 narcotic agent Substances 0.000 description 1
- 230000003533 narcotic effect Effects 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 235000019198 oils Nutrition 0.000 description 1
- 230000003204 osmotic effect Effects 0.000 description 1
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 1
- 210000004303 peritoneum Anatomy 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 229960003424 phenylacetic acid Drugs 0.000 description 1
- 239000003279 phenylacetic acid Substances 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 1
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
- 230000002980 postoperative effect Effects 0.000 description 1
- 230000003389 potentiating effect Effects 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- WYVAMUWZEOHJOQ-UHFFFAOYSA-N propionic anhydride Chemical compound CCC(=O)OC(=O)CC WYVAMUWZEOHJOQ-UHFFFAOYSA-N 0.000 description 1
- 208000018299 prostration Diseases 0.000 description 1
- 229940001470 psychoactive drug Drugs 0.000 description 1
- 239000004089 psychotropic agent Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 230000002787 reinforcement Effects 0.000 description 1
- 238000006798 ring closing metathesis reaction Methods 0.000 description 1
- 238000012216 screening Methods 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
- 239000000932 sedative agent Substances 0.000 description 1
- 229940125723 sedative agent Drugs 0.000 description 1
- 235000002639 sodium chloride Nutrition 0.000 description 1
- HRZFUMHJMZEROT-UHFFFAOYSA-L sodium disulfite Chemical compound [Na+].[Na+].[O-]S(=O)S([O-])(=O)=O HRZFUMHJMZEROT-UHFFFAOYSA-L 0.000 description 1
- 235000010262 sodium metabisulphite Nutrition 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 230000002048 spasmolytic effect Effects 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 230000002269 spontaneous effect Effects 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 239000003765 sweetening agent Substances 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 235000012222 talc Nutrition 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 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
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- IDELNEDBPWKHGK-UHFFFAOYSA-N thiobutabarbital Chemical compound CCC(C)C1(CC)C(=O)NC(=S)NC1=O IDELNEDBPWKHGK-UHFFFAOYSA-N 0.000 description 1
- 231100000041 toxicology testing Toxicity 0.000 description 1
- 239000003204 tranquilizing agent Substances 0.000 description 1
- 230000002936 tranquilizing effect Effects 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- 125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 description 1
- GKASDNZWUGIAMG-UHFFFAOYSA-N triethyl orthoformate Chemical compound CCOC(OCC)OCC GKASDNZWUGIAMG-UHFFFAOYSA-N 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- 210000003462 vein Anatomy 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D513/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00
- C07D513/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00 in which the condensed system contains two hetero rings
- C07D513/04—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
- A61P25/22—Anxiolytics
-
- 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
- A61P25/24—Antidepressants
-
- 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
- A61P25/26—Psychostimulants, e.g. nicotine, cocaine
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Medicinal Chemistry (AREA)
- General Health & Medical Sciences (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)
- Veterinary Medicine (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Biomedical Technology (AREA)
- Public Health (AREA)
- Psychiatry (AREA)
- Pain & Pain Management (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| HU854304A HU197019B (en) | 1985-11-12 | 1985-11-12 | Process for producing thiqzolo (4,5-c) quinoline derivatives and pharmaceuticals comprising same |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| NO864518D0 NO864518D0 (no) | 1986-11-12 |
| NO864518L true NO864518L (no) | 1987-05-13 |
Family
ID=10967593
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO864518A NO864518L (no) | 1985-11-12 | 1986-11-12 | Fremgangsmaate for fremstilling av thiazolo(4,5-c)kinoliner |
Country Status (24)
| Country | Link |
|---|---|
| US (1) | US4904669A (hu) |
| JP (1) | JPS62161792A (hu) |
| CN (1) | CN86107754A (hu) |
| AU (1) | AU592384B2 (hu) |
| BE (1) | BE905719A (hu) |
| BG (1) | BG46156A3 (hu) |
| CH (1) | CH670829A5 (hu) |
| DD (1) | DD254202A5 (hu) |
| DE (1) | DE3638563A1 (hu) |
| DK (1) | DK539786A (hu) |
| ES (1) | ES2002543A6 (hu) |
| FI (1) | FI864611A (hu) |
| FR (1) | FR2603588A1 (hu) |
| GB (1) | GB2184117B (hu) |
| HU (1) | HU197019B (hu) |
| IL (1) | IL80611A0 (hu) |
| IT (1) | IT1213379B (hu) |
| NL (1) | NL8602878A (hu) |
| NO (1) | NO864518L (hu) |
| PL (1) | PL148186B1 (hu) |
| SE (1) | SE8604839L (hu) |
| SU (1) | SU1544190A3 (hu) |
| YU (1) | YU192186A (hu) |
| ZA (1) | ZA868583B (hu) |
Families Citing this family (33)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| HU199423B (en) * | 1987-04-24 | 1990-02-28 | Egyt Gyogyszervegyeszeti Gyar | Process for producing 3-amino-4-/ethylthio/-quinoline and pharmaceutical compositions comprising such compounds |
| US6110929A (en) * | 1998-07-28 | 2000-08-29 | 3M Innovative Properties Company | Oxazolo, thiazolo and selenazolo [4,5-c]-quinolin-4-amines and analogs thereof |
| US6677347B2 (en) * | 2000-12-08 | 2004-01-13 | 3M Innovative Properties Company | Sulfonamido ether substituted imidazoquinolines |
| US20040214851A1 (en) * | 2003-04-28 | 2004-10-28 | 3M Innovative Properties Company | Compositions and methods for induction of opioid receptors |
| BRPI0412902A (pt) * | 2003-08-12 | 2006-09-26 | 3M Innovative Properties Co | compostos contendo imidazo substituìdo por oxima |
| CA2536136C (en) * | 2003-08-27 | 2012-10-30 | 3M Innovative Properties Company | Aryloxy and arylalkyleneoxy substituted imidazoquinolines |
| AU2004270201A1 (en) * | 2003-09-05 | 2005-03-17 | 3M Innovative Properties Company | Treatment for CD5+ B cell lymphoma |
| CA2540541C (en) * | 2003-10-03 | 2012-03-27 | 3M Innovative Properties Company | Alkoxy substituted imidazoquinolines |
| US20090075980A1 (en) * | 2003-10-03 | 2009-03-19 | Coley Pharmaceutical Group, Inc. | Pyrazolopyridines and Analogs Thereof |
| US7544697B2 (en) * | 2003-10-03 | 2009-06-09 | Coley Pharmaceutical Group, Inc. | Pyrazolopyridines and analogs thereof |
| WO2005048933A2 (en) | 2003-11-14 | 2005-06-02 | 3M Innovative Properties Company | Oxime substituted imidazo ring compounds |
| US8598192B2 (en) * | 2003-11-14 | 2013-12-03 | 3M Innovative Properties Company | Hydroxylamine substituted imidazoquinolines |
| AU2004293078B2 (en) * | 2003-11-25 | 2012-01-19 | 3M Innovative Properties Company | Substituted imidazo ring systems and methods |
| EP1701955A1 (en) * | 2003-12-29 | 2006-09-20 | 3M Innovative Properties Company | Arylalkenyl and arylalkynyl substituted imidazoquinolines |
| WO2005066169A2 (en) * | 2003-12-30 | 2005-07-21 | 3M Innovative Properties Company | Imidazoquinolinyl, imidazopyridinyl, and imidazonaphthyridinyl sulfonamides |
| CA2559863A1 (en) * | 2004-03-24 | 2005-10-13 | 3M Innovative Properties Company | Amide substituted imidazopyridines, imidazoquinolines, and imidazonaphthyridines |
| WO2005123080A2 (en) * | 2004-06-15 | 2005-12-29 | 3M Innovative Properties Company | Nitrogen-containing heterocyclyl substituted imidazoquinolines and imidazonaphthyridines |
| WO2006038923A2 (en) * | 2004-06-18 | 2006-04-13 | 3M Innovative Properties Company | Aryl substituted imidazonaphthyridines |
| WO2006009832A1 (en) * | 2004-06-18 | 2006-01-26 | 3M Innovative Properties Company | Substituted imidazo ring systems and methods |
| US7915281B2 (en) * | 2004-06-18 | 2011-03-29 | 3M Innovative Properties Company | Isoxazole, dihydroisoxazole, and oxadiazole substituted imidazo ring compounds and method |
| US8026366B2 (en) * | 2004-06-18 | 2011-09-27 | 3M Innovative Properties Company | Aryloxy and arylalkyleneoxy substituted thiazoloquinolines and thiazolonaphthyridines |
| WO2006026760A2 (en) * | 2004-09-02 | 2006-03-09 | 3M Innovative Properties Company | 1-amino imidazo-containing compounds and methods |
| WO2006063072A2 (en) * | 2004-12-08 | 2006-06-15 | 3M Innovative Properties Company | Immunomodulatory compositions, combinations and methods |
| US7943609B2 (en) * | 2004-12-30 | 2011-05-17 | 3M Innovative Proprerties Company | Chiral fused [1,2]imidazo[4,5-C] ring compounds |
| ES2392648T3 (es) | 2004-12-30 | 2012-12-12 | 3M Innovative Properties Company | Compuestos quirales sustituidos que contienen un núcleo 1,2-imidazo-4,5-c condensado |
| US9248127B2 (en) * | 2005-02-04 | 2016-02-02 | 3M Innovative Properties Company | Aqueous gel formulations containing immune response modifiers |
| WO2007120121A2 (en) * | 2005-02-09 | 2007-10-25 | Coley Pharmaceutical Group, Inc. | Oxime and hydroxylamine substituted thiazolo[4,5-c] ring compounds and methods |
| EP1846405A2 (en) | 2005-02-11 | 2007-10-24 | 3M Innovative Properties Company | Oxime and hydroxylamine substituted imidazo 4,5-c ring compounds and methods |
| AU2006232377A1 (en) | 2005-04-01 | 2006-10-12 | Coley Pharmaceutical Group, Inc. | Pyrazolopyridine-1,4-diamines and analogs thereof |
| CA2602590A1 (en) | 2005-04-01 | 2006-10-12 | Coley Pharmaceutical Group, Inc. | 1-substituted pyrazolo (3,4-c) ring compounds as modulators of cytokine biosynthesis for the treatment of viral infections and neoplastic diseases |
| WO2008008432A2 (en) * | 2006-07-12 | 2008-01-17 | Coley Pharmaceutical Group, Inc. | Substituted chiral fused( 1,2) imidazo (4,5-c) ring compounds and methods |
| KR20210082473A (ko) | 2018-10-23 | 2021-07-05 | 바스프 에스이 | 트리시클릭 살충 화합물 |
| WO2021209265A1 (en) | 2020-04-14 | 2021-10-21 | Basf Se | Tricyclic pesticidal compounds |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB2024207A (en) * | 1978-05-26 | 1980-01-09 | Lepetit Spa | New tricyclic ortho-fused heterocyclic compounds |
| HU196308B (en) * | 1985-11-12 | 1988-11-28 | Egyt Gyogyszervegyeszeti Gyar | Process for producing pharmaceutical compositions containing 2-methyl-thiazolo/4,5-c/quinoline as active component |
-
1985
- 1985-11-12 HU HU854304A patent/HU197019B/hu not_active IP Right Cessation
-
1986
- 1986-11-07 BE BE1/011572A patent/BE905719A/fr not_active IP Right Cessation
- 1986-11-10 CH CH4491/86A patent/CH670829A5/de not_active IP Right Cessation
- 1986-11-12 IT IT8622312A patent/IT1213379B/it active
- 1986-11-12 GB GB8627043A patent/GB2184117B/en not_active Expired
- 1986-11-12 SU SU864028529A patent/SU1544190A3/ru active
- 1986-11-12 FI FI864611A patent/FI864611A/fi not_active Application Discontinuation
- 1986-11-12 BG BG77078A patent/BG46156A3/xx unknown
- 1986-11-12 JP JP61267869A patent/JPS62161792A/ja active Pending
- 1986-11-12 DD DD86296208A patent/DD254202A5/de not_active IP Right Cessation
- 1986-11-12 YU YU01921/86A patent/YU192186A/xx unknown
- 1986-11-12 AU AU65089/86A patent/AU592384B2/en not_active Expired - Fee Related
- 1986-11-12 FR FR8615655A patent/FR2603588A1/fr active Pending
- 1986-11-12 DE DE19863638563 patent/DE3638563A1/de not_active Withdrawn
- 1986-11-12 ZA ZA868583A patent/ZA868583B/xx unknown
- 1986-11-12 US US06/929,353 patent/US4904669A/en not_active Expired - Fee Related
- 1986-11-12 CN CN198686107754A patent/CN86107754A/zh active Pending
- 1986-11-12 NO NO864518A patent/NO864518L/no unknown
- 1986-11-12 IL IL80611A patent/IL80611A0/xx unknown
- 1986-11-12 NL NL8602878A patent/NL8602878A/nl not_active Application Discontinuation
- 1986-11-12 SE SE8604839A patent/SE8604839L/xx not_active Application Discontinuation
- 1986-11-12 PL PL1986262346A patent/PL148186B1/pl unknown
- 1986-11-12 DK DK539786A patent/DK539786A/da not_active Application Discontinuation
- 1986-11-12 ES ES8603003A patent/ES2002543A6/es not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| ES2002543A6 (es) | 1988-08-16 |
| US4904669A (en) | 1990-02-27 |
| CN86107754A (zh) | 1987-08-05 |
| SE8604839L (sv) | 1987-05-13 |
| YU192186A (en) | 1988-10-31 |
| JPS62161792A (ja) | 1987-07-17 |
| HUT44260A (en) | 1988-02-29 |
| FI864611A0 (fi) | 1986-11-12 |
| IT1213379B (it) | 1989-12-20 |
| SE8604839D0 (sv) | 1986-11-12 |
| FR2603588A1 (fr) | 1988-03-11 |
| NL8602878A (nl) | 1987-06-01 |
| GB8627043D0 (en) | 1986-12-10 |
| BE905719A (fr) | 1987-05-07 |
| IT8622312A0 (it) | 1986-11-12 |
| DK539786D0 (da) | 1986-11-12 |
| DD254202A5 (de) | 1988-02-17 |
| ZA868583B (en) | 1987-08-26 |
| SU1544190A3 (ru) | 1990-02-15 |
| NO864518D0 (no) | 1986-11-12 |
| DE3638563A1 (de) | 1987-06-25 |
| AU6508986A (en) | 1987-05-14 |
| FI864611A (fi) | 1987-05-13 |
| BG46156A3 (en) | 1989-10-16 |
| PL148186B1 (en) | 1989-09-30 |
| GB2184117B (en) | 1989-10-11 |
| HU197019B (en) | 1989-02-28 |
| DK539786A (da) | 1987-05-13 |
| IL80611A0 (en) | 1987-02-27 |
| GB2184117A (en) | 1987-06-17 |
| PL262346A1 (en) | 1988-03-03 |
| AU592384B2 (en) | 1990-01-11 |
| CH670829A5 (hu) | 1989-07-14 |
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