HU184721B - Process for preparation of basic thioindazole derivatives - Google Patents
Process for preparation of basic thioindazole derivatives Download PDFInfo
- Publication number
- HU184721B HU184721B HU80367A HU36780A HU184721B HU 184721 B HU184721 B HU 184721B HU 80367 A HU80367 A HU 80367A HU 36780 A HU36780 A HU 36780A HU 184721 B HU184721 B HU 184721B
- Authority
- HU
- Hungary
- Prior art keywords
- formula
- benzyl
- compound
- preparation
- indazole
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 13
- 238000002360 preparation method Methods 0.000 title claims description 12
- 230000008569 process Effects 0.000 title claims description 9
- 150000001875 compounds Chemical class 0.000 claims abstract description 25
- -1 2-benzyl-3- (3-dimethylaminopropylsulfinyl) -2H-indazole Chemical compound 0.000 claims description 31
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 claims description 22
- 238000006243 chemical reaction Methods 0.000 claims description 22
- 150000003839 salts Chemical class 0.000 claims description 10
- VPMZGRVNLHDREW-UHFFFAOYSA-N 3-(2-benzylindazol-3-yl)sulfanyl-n,n-dimethylpropan-1-amine Chemical compound N1=C2C=CC=CC2=C(SCCCN(C)C)N1CC1=CC=CC=C1 VPMZGRVNLHDREW-UHFFFAOYSA-N 0.000 claims description 9
- 229910052783 alkali metal Inorganic materials 0.000 claims description 7
- 239000003054 catalyst Substances 0.000 claims description 6
- 125000005843 halogen group Chemical group 0.000 claims description 5
- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 claims description 4
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- 239000008194 pharmaceutical composition Substances 0.000 claims description 4
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- QKIUAMUSENSFQQ-UHFFFAOYSA-N dimethylazanide Chemical compound C[N-]C QKIUAMUSENSFQQ-UHFFFAOYSA-N 0.000 claims 3
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- HSAYSFNFCZEPCN-UHFFFAOYSA-N 3-(dimethylamino)propane-1-thiol Chemical compound CN(C)CCCS HSAYSFNFCZEPCN-UHFFFAOYSA-N 0.000 claims 1
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- BQSZFOGVHFAQGY-UHFFFAOYSA-N 3-indazol-2-ylsulfanyl-N,N-dimethylpropan-1-amine Chemical compound CN(C)CCCSN1N=C2C=CC=CC2=C1 BQSZFOGVHFAQGY-UHFFFAOYSA-N 0.000 claims 1
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- 239000011593 sulfur Substances 0.000 abstract 3
- 125000003453 indazolyl group Chemical class N1N=C(C2=C1C=CC=C2)* 0.000 abstract 2
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- CNBGNNVCVSKAQZ-UHFFFAOYSA-N benzydamine Chemical compound C12=CC=CC=C2C(OCCCN(C)C)=NN1CC1=CC=CC=C1 CNBGNNVCVSKAQZ-UHFFFAOYSA-N 0.000 description 22
- 239000000203 mixture Substances 0.000 description 17
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- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- RPACBEVZENYWOL-XFULWGLBSA-M sodium;(2r)-2-[6-(4-chlorophenoxy)hexyl]oxirane-2-carboxylate Chemical compound [Na+].C=1C=C(Cl)C=CC=1OCCCCCC[C@]1(C(=O)[O-])CO1 RPACBEVZENYWOL-XFULWGLBSA-M 0.000 description 1
- FISGLHSNQHXMGY-UHFFFAOYSA-N sodium;aminoazanide Chemical compound [Na+].[NH-]N FISGLHSNQHXMGY-UHFFFAOYSA-N 0.000 description 1
- 239000011877 solvent mixture Substances 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- 150000003459 sulfonic acid esters Chemical group 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 238000007910 systemic administration Methods 0.000 description 1
- 229940095064 tartrate Drugs 0.000 description 1
- 229940124597 therapeutic agent Drugs 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 238000002211 ultraviolet spectrum Methods 0.000 description 1
- 210000001215 vagina Anatomy 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/54—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings condensed with carbocyclic rings or ring systems
- C07D231/56—Benzopyrazoles; Hydrogenated benzopyrazoles
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pain & Pain Management (AREA)
- Pharmacology & Pharmacy (AREA)
- Rheumatology (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Thiazole And Isothizaole Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IT20305/79A IT1110282B (it) | 1979-02-19 | 1979-02-19 | Tio-indazoli basici |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| HU184721B true HU184721B (en) | 1984-10-29 |
Family
ID=11165582
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HU80367A HU184721B (en) | 1979-02-19 | 1980-02-18 | Process for preparation of basic thioindazole derivatives |
Country Status (22)
| Country | Link |
|---|---|
| US (1) | US4264618A (enExample) |
| JP (1) | JPS605590B2 (enExample) |
| AT (1) | ATA91780A (enExample) |
| AU (1) | AU518489B2 (enExample) |
| CA (1) | CA1131234A (enExample) |
| DD (2) | DD157255A5 (enExample) |
| DE (1) | DE3000690A1 (enExample) |
| DK (1) | DK69880A (enExample) |
| ES (1) | ES488719A0 (enExample) |
| FI (1) | FI800295A7 (enExample) |
| FR (3) | FR2453156A1 (enExample) |
| GB (3) | GB2043069B (enExample) |
| HU (1) | HU184721B (enExample) |
| IE (1) | IE49399B1 (enExample) |
| IL (1) | IL59271A0 (enExample) |
| IT (1) | IT1110282B (enExample) |
| NL (1) | NL8000610A (enExample) |
| PL (1) | PL130717B1 (enExample) |
| PT (1) | PT70835A (enExample) |
| SE (1) | SE8001279L (enExample) |
| SU (1) | SU1042614A3 (enExample) |
| YU (3) | YU39880A (enExample) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6190642B1 (en) | 1988-02-19 | 2001-02-20 | Dentsply Research & Development Corp. | Irrigating and lavage compositions |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3145215A (en) * | 1961-12-19 | 1964-08-18 | Sterling Drug Inc | Indazole derivatives |
| GB1054833A (enExample) * | 1963-08-09 | |||
| US3428634A (en) * | 1965-03-13 | 1969-02-18 | Acraf | 3-tertiary amino alkoxy-1-hydrocarbon indazoles |
| US3637738A (en) * | 1969-02-12 | 1972-01-25 | Ciba Geigy Corp | Cycloalkano(c)pyrazole ethers |
| US4182769A (en) * | 1977-02-09 | 1980-01-08 | E. I. Du Pont De Nemours And Company | Anti-inflammatory 1-substituted-4,5-diaryl-2-(substituted-thio) imidazoles and their corresponding sulfoxides and sulfones |
-
1979
- 1979-02-19 IT IT20305/79A patent/IT1110282B/it active
- 1979-12-11 US US06/102,509 patent/US4264618A/en not_active Expired - Lifetime
-
1980
- 1980-01-10 DE DE19803000690 patent/DE3000690A1/de not_active Withdrawn
- 1980-01-30 IL IL59271A patent/IL59271A0/xx unknown
- 1980-01-31 NL NL8000610A patent/NL8000610A/nl not_active Application Discontinuation
- 1980-01-31 FI FI800295A patent/FI800295A7/fi not_active Application Discontinuation
- 1980-02-06 FR FR8002622A patent/FR2453156A1/fr active Granted
- 1980-02-07 AU AU55318/80A patent/AU518489B2/en not_active Ceased
- 1980-02-14 YU YU00398/80A patent/YU39880A/xx unknown
- 1980-02-14 CA CA345,682A patent/CA1131234A/en not_active Expired
- 1980-02-14 GB GB8005082A patent/GB2043069B/en not_active Expired
- 1980-02-15 PT PT70835A patent/PT70835A/pt unknown
- 1980-02-18 DK DK69880A patent/DK69880A/da not_active Application Discontinuation
- 1980-02-18 SE SE8001279A patent/SE8001279L/xx not_active Application Discontinuation
- 1980-02-18 ES ES488719A patent/ES488719A0/es active Granted
- 1980-02-18 IE IE296/80A patent/IE49399B1/en unknown
- 1980-02-18 SU SU802883703A patent/SU1042614A3/ru active
- 1980-02-18 JP JP55018946A patent/JPS605590B2/ja not_active Expired
- 1980-02-18 PL PL1980222090A patent/PL130717B1/pl unknown
- 1980-02-18 HU HU80367A patent/HU184721B/hu unknown
- 1980-02-19 AT AT0091780A patent/ATA91780A/de not_active IP Right Cessation
- 1980-02-19 DD DD80228371A patent/DD157255A5/de unknown
- 1980-02-19 DD DD80219140A patent/DD149806A5/de unknown
- 1980-07-03 FR FR8014867A patent/FR2450823A1/fr active Granted
- 1980-07-03 FR FR8014866A patent/FR2450822A1/fr active Granted
-
1982
- 1982-10-15 GB GB08229492A patent/GB2108957B/en not_active Expired
- 1982-10-15 GB GB08229493A patent/GB2108958B/en not_active Expired
- 1982-11-22 YU YU02606/82A patent/YU260682A/xx unknown
- 1982-11-22 YU YU02605/82A patent/YU260582A/xx unknown
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