DD254202A5 - Verfahren zur herstellung von thiazole(4,5-c)chinolin-derivaten - Google Patents
Verfahren zur herstellung von thiazole(4,5-c)chinolin-derivaten Download PDFInfo
- Publication number
- DD254202A5 DD254202A5 DD86296208A DD29620886A DD254202A5 DD 254202 A5 DD254202 A5 DD 254202A5 DD 86296208 A DD86296208 A DD 86296208A DD 29620886 A DD29620886 A DD 29620886A DD 254202 A5 DD254202 A5 DD 254202A5
- Authority
- DD
- German Democratic Republic
- Prior art keywords
- general formula
- quinoline
- acid
- reaction
- acid addition
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 34
- 238000002360 preparation method Methods 0.000 title claims description 9
- 230000008569 process Effects 0.000 title claims description 7
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical class N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 title 1
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract description 42
- 239000002253 acid Substances 0.000 claims abstract description 39
- 150000003839 salts Chemical class 0.000 claims abstract description 33
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 10
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 9
- 239000001257 hydrogen Substances 0.000 claims abstract description 9
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 9
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 7
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 7
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 6
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 6
- 150000002367 halogens Chemical class 0.000 claims abstract description 6
- 125000005843 halogen group Chemical group 0.000 claims abstract description 5
- 125000003884 phenylalkyl group Chemical group 0.000 claims abstract description 5
- 125000001424 substituent group Chemical group 0.000 claims abstract description 5
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- 238000002156 mixing Methods 0.000 description 1
- 229960005181 morphine Drugs 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 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
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 150000002905 orthoesters Chemical class 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
- 238000005192 partition Methods 0.000 description 1
- 239000008194 pharmaceutical composition Substances 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
- 235000011007 phosphoric acid Nutrition 0.000 description 1
- 229920001592 potato starch Polymers 0.000 description 1
- 230000003389 potentiating effect Effects 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- WYVAMUWZEOHJOQ-UHFFFAOYSA-N propionic anhydride Chemical compound CCC(=O)OC(=O)CC WYVAMUWZEOHJOQ-UHFFFAOYSA-N 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 102000005962 receptors Human genes 0.000 description 1
- 108020003175 receptors Proteins 0.000 description 1
- 239000013558 reference substance Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 230000002787 reinforcement Effects 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 230000028527 righting reflex Effects 0.000 description 1
- 238000006798 ring closing metathesis reaction Methods 0.000 description 1
- VAGCNQLBOMUSCM-UHFFFAOYSA-N s-quinolin-2-ylthiohydroxylamine Chemical compound C1=CC=CC2=NC(SN)=CC=C21 VAGCNQLBOMUSCM-UHFFFAOYSA-N 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
- 230000035939 shock Effects 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
- 230000002048 spasmolytic effect Effects 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 239000000126 substance 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
- 239000003826 tablet Substances 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
- 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
- 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
- 210000003462 vein Anatomy 0.000 description 1
- 238000009736 wetting Methods 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)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Public Health (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (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 (1)
| Publication Number | Publication Date |
|---|---|
| DD254202A5 true DD254202A5 (de) | 1988-02-17 |
Family
ID=10967593
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DD86296208A DD254202A5 (de) | 1985-11-12 | 1986-11-12 | Verfahren zur herstellung von thiazole(4,5-c)chinolin-derivaten |
Country Status (24)
| Country | Link |
|---|---|
| US (1) | US4904669A (https=) |
| JP (1) | JPS62161792A (https=) |
| CN (1) | CN86107754A (https=) |
| AU (1) | AU592384B2 (https=) |
| BE (1) | BE905719A (https=) |
| BG (1) | BG46156A3 (https=) |
| CH (1) | CH670829A5 (https=) |
| DD (1) | DD254202A5 (https=) |
| DE (1) | DE3638563A1 (https=) |
| DK (1) | DK539786A (https=) |
| ES (1) | ES2002543A6 (https=) |
| FI (1) | FI864611A7 (https=) |
| FR (1) | FR2603588A1 (https=) |
| GB (1) | GB2184117B (https=) |
| HU (1) | HU197019B (https=) |
| IL (1) | IL80611A0 (https=) |
| IT (1) | IT1213379B (https=) |
| NL (1) | NL8602878A (https=) |
| NO (1) | NO864518L (https=) |
| PL (1) | PL148186B1 (https=) |
| SE (1) | SE8604839L (https=) |
| SU (1) | SU1544190A3 (https=) |
| YU (1) | YU192186A (https=) |
| ZA (1) | ZA868583B (https=) |
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 |
| BRPI0413558A (pt) * | 2003-08-12 | 2006-10-17 | 3M Innovative Properties Co | compostos contendo imidazo substituìdo por hidroxilamina |
| MXPA06002199A (es) * | 2003-08-27 | 2006-05-22 | 3M Innovative Properties Co | Imidazoquinolinas sustituidas con grupos ariloxi o arilalquilenoxi. |
| CA2537763A1 (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 |
| US7897767B2 (en) | 2003-11-14 | 2011-03-01 | 3M Innovative Properties Company | Oxime substituted imidazoquinolines |
| WO2005048945A2 (en) * | 2003-11-14 | 2005-06-02 | 3M Innovative Properties Company | Hydroxylamine substituted imidazo ring compounds |
| WO2005051317A2 (en) * | 2003-11-25 | 2005-06-09 | 3M Innovative Properties Company | Substituted imidazo ring systems and methods |
| JP2007517035A (ja) * | 2003-12-29 | 2007-06-28 | スリーエム イノベイティブ プロパティズ カンパニー | アリールアルケニルおよびアリールアルキニル置換されたイミダゾキノリン |
| EP1699788A2 (en) * | 2003-12-30 | 2006-09-13 | 3M Innovative Properties Company | Imidazoquinolinyl, imidazopyridinyl and imidazonaphthyridinyl sulfonamides |
| WO2005094531A2 (en) * | 2004-03-24 | 2005-10-13 | 3M Innovative Properties Company | Amide substituted imidazopyridines, imidazoquinolines, and imidazonaphthyridines |
| US8017779B2 (en) * | 2004-06-15 | 2011-09-13 | 3M Innovative Properties Company | Nitrogen containing heterocyclyl substituted imidazoquinolines and imidazonaphthyridines |
| US20070259881A1 (en) * | 2004-06-18 | 2007-11-08 | Dellaria Joseph F Jr | 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 |
| US7897609B2 (en) * | 2004-06-18 | 2011-03-01 | 3M Innovative Properties Company | Aryl substituted imidazonaphthyridines |
| US8026366B2 (en) * | 2004-06-18 | 2011-09-27 | 3M Innovative Properties Company | Aryloxy and arylalkyleneoxy substituted thiazoloquinolines and thiazolonaphthyridines |
| US20090270443A1 (en) * | 2004-09-02 | 2009-10-29 | Doris Stoermer | 1-amino imidazo-containing compounds and methods |
| US20110070575A1 (en) * | 2004-12-08 | 2011-03-24 | Coley Pharmaceutical Group, Inc. | Immunomodulatory Compositions, Combinations and Methods |
| JP5543068B2 (ja) * | 2004-12-30 | 2014-07-09 | スリーエム イノベイティブ プロパティズ カンパニー | キラル縮合［１，２］イミダゾ［４，５−ｃ］環状化合物 |
| AU2005326708C1 (en) | 2004-12-30 | 2012-08-30 | 3M Innovative Properties Company | Substituted chiral fused [1,2]imidazo[4,5-c] ring compounds |
| WO2006084251A2 (en) | 2005-02-04 | 2006-08-10 | Coley Pharmaceutical Group, Inc. | Aqueous gel formulations containing immune reponse modifiers |
| AU2006338521A1 (en) * | 2005-02-09 | 2007-10-11 | Coley Pharmaceutical Group, Inc. | Oxime and hydroxylamine substituted thiazolo(4,5-c) ring compounds and methods |
| CA2597587A1 (en) | 2005-02-11 | 2006-08-17 | Coley Pharmaceutical Group, Inc. | Oxime and hydroxylamine substituted imidazo[4,5-c] ring compounds and methods |
| JP2008535832A (ja) | 2005-04-01 | 2008-09-04 | コーリー ファーマシューティカル グループ，インコーポレイテッド | ピラゾロピリジン−１，４−ジアミン、およびそのアナログ |
| JP2008538550A (ja) | 2005-04-01 | 2008-10-30 | コーリー ファーマシューティカル グループ，インコーポレイテッド | ウイルス感染および腫瘍性疾患を処置するためのサイトカイン生合成の調節因子としての１−置換ピラゾロ（３，４−ｃ）環状化合物 |
| US7906506B2 (en) * | 2006-07-12 | 2011-03-15 | 3M Innovative Properties Company | Substituted chiral fused [1,2] imidazo [4,5-c] ring compounds and methods |
| JP7443357B2 (ja) | 2018-10-23 | 2024-03-05 | ビーエーエスエフ ソシエタス・ヨーロピア | 三環式の殺有害生物化合物 |
| EP4136086A1 (en) | 2020-04-14 | 2023-02-22 | 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 US US06/929,353 patent/US4904669A/en not_active Expired - Fee Related
- 1986-11-12 FI FI864611A patent/FI864611A7/fi not_active Application Discontinuation
- 1986-11-12 CN CN198686107754A patent/CN86107754A/zh active Pending
- 1986-11-12 FR FR8615655A patent/FR2603588A1/fr active Pending
- 1986-11-12 JP JP61267869A patent/JPS62161792A/ja active Pending
- 1986-11-12 SU SU864028529A patent/SU1544190A3/ru active
- 1986-11-12 YU YU01921/86A patent/YU192186A/xx unknown
- 1986-11-12 SE SE8604839A patent/SE8604839L/xx not_active Application Discontinuation
- 1986-11-12 DE DE19863638563 patent/DE3638563A1/de not_active Withdrawn
- 1986-11-12 IT IT8622312A patent/IT1213379B/it active
- 1986-11-12 GB GB8627043A patent/GB2184117B/en not_active Expired
- 1986-11-12 DD DD86296208A patent/DD254202A5/de not_active IP Right Cessation
- 1986-11-12 NO NO864518A patent/NO864518L/no unknown
- 1986-11-12 NL NL8602878A patent/NL8602878A/nl not_active Application Discontinuation
- 1986-11-12 AU AU65089/86A patent/AU592384B2/en not_active Expired - Fee Related
- 1986-11-12 IL IL80611A patent/IL80611A0/xx unknown
- 1986-11-12 DK DK539786A patent/DK539786A/da not_active Application Discontinuation
- 1986-11-12 PL PL1986262346A patent/PL148186B1/pl unknown
- 1986-11-12 ZA ZA868583A patent/ZA868583B/xx unknown
- 1986-11-12 BG BG77078A patent/BG46156A3/xx unknown
- 1986-11-12 ES ES8603003A patent/ES2002543A6/es not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| GB8627043D0 (en) | 1986-12-10 |
| IL80611A0 (en) | 1987-02-27 |
| SE8604839D0 (sv) | 1986-11-12 |
| SE8604839L (sv) | 1987-05-13 |
| IT1213379B (it) | 1989-12-20 |
| GB2184117B (en) | 1989-10-11 |
| FI864611A7 (fi) | 1987-05-13 |
| AU592384B2 (en) | 1990-01-11 |
| HUT44260A (en) | 1988-02-29 |
| ES2002543A6 (es) | 1988-08-16 |
| YU192186A (en) | 1988-10-31 |
| FI864611A0 (fi) | 1986-11-12 |
| IT8622312A0 (it) | 1986-11-12 |
| US4904669A (en) | 1990-02-27 |
| NL8602878A (nl) | 1987-06-01 |
| FR2603588A1 (fr) | 1988-03-11 |
| CH670829A5 (https=) | 1989-07-14 |
| NO864518L (no) | 1987-05-13 |
| BE905719A (fr) | 1987-05-07 |
| CN86107754A (zh) | 1987-08-05 |
| SU1544190A3 (ru) | 1990-02-15 |
| NO864518D0 (no) | 1986-11-12 |
| GB2184117A (en) | 1987-06-17 |
| DK539786A (da) | 1987-05-13 |
| DE3638563A1 (de) | 1987-06-25 |
| DK539786D0 (da) | 1986-11-12 |
| ZA868583B (en) | 1987-08-26 |
| JPS62161792A (ja) | 1987-07-17 |
| AU6508986A (en) | 1987-05-14 |
| HU197019B (en) | 1989-02-28 |
| BG46156A3 (en) | 1989-10-16 |
| PL148186B1 (en) | 1989-09-30 |
| PL262346A1 (en) | 1988-03-03 |
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Legal Events
| Date | Code | Title | Description |
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| ENJ | Ceased due to non-payment of renewal fee |