FI114024B - Menetelmä terapeuttisesti käyttökelpoisten tioksantenonijohdannaisten valmistamiseksi - Google Patents
Menetelmä terapeuttisesti käyttökelpoisten tioksantenonijohdannaisten valmistamiseksi Download PDFInfo
- Publication number
- FI114024B FI114024B FI922694A FI922694A FI114024B FI 114024 B FI114024 B FI 114024B FI 922694 A FI922694 A FI 922694A FI 922694 A FI922694 A FI 922694A FI 114024 B FI114024 B FI 114024B
- Authority
- FI
- Finland
- Prior art keywords
- formula
- compound
- lower alkyl
- hydrogen
- ethyl
- Prior art date
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- 238000000034 method Methods 0.000 title claims abstract description 26
- 238000002360 preparation method Methods 0.000 title claims description 7
- YRHRIQCWCFGUEQ-UHFFFAOYSA-N thioxanthen-9-one Chemical class C1=CC=C2C(=O)C3=CC=CC=C3SC2=C1 YRHRIQCWCFGUEQ-UHFFFAOYSA-N 0.000 title description 5
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 29
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 23
- 239000001257 hydrogen Substances 0.000 claims abstract description 23
- 150000003839 salts Chemical class 0.000 claims abstract description 20
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims abstract description 19
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 14
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 12
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 8
- 150000002431 hydrogen Chemical class 0.000 claims abstract description 7
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 6
- 150000002367 halogens Chemical class 0.000 claims abstract description 6
- GRVDJDISBSALJP-UHFFFAOYSA-N methyloxidanyl Chemical group [O]C GRVDJDISBSALJP-UHFFFAOYSA-N 0.000 claims abstract description 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 3
- 239000012453 solvate Substances 0.000 claims abstract description 3
- 125000004005 formimidoyl group Chemical group [H]\N=C(/[H])* 0.000 claims abstract 5
- 150000001875 compounds Chemical class 0.000 claims description 48
- 239000002253 acid Substances 0.000 claims description 15
- ZMANZCXQSJIPKH-UHFFFAOYSA-N triethylamine Natural products CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 14
- ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 claims description 11
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 11
- 150000001412 amines Chemical class 0.000 claims description 10
- 101100294106 Caenorhabditis elegans nhr-3 gene Proteins 0.000 claims description 6
- 150000002923 oximes Chemical class 0.000 claims description 6
- 239000003795 chemical substances by application Substances 0.000 claims description 4
- KERBAAIBDHEFDD-UHFFFAOYSA-N n-ethylformamide Chemical compound CCNC=O KERBAAIBDHEFDD-UHFFFAOYSA-N 0.000 claims description 4
- FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 claims description 3
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 claims description 2
- 125000003545 alkoxy group Chemical group 0.000 claims description 2
- 230000018044 dehydration Effects 0.000 claims description 2
- 238000006297 dehydration reaction Methods 0.000 claims description 2
- NAMOLZVVTPNNTE-UHFFFAOYSA-N n-[[1-[2-(diethylamino)ethylamino]-9-oxothioxanthen-4-yl]methyl]methanesulfonamide Chemical compound S1C2=CC=CC=C2C(=O)C2=C1C(CNS(C)(=O)=O)=CC=C2NCCN(CC)CC NAMOLZVVTPNNTE-UHFFFAOYSA-N 0.000 claims description 2
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- 125000001475 halogen functional group Chemical group 0.000 claims 1
- 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 claims 1
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- 238000001914 filtration Methods 0.000 description 6
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- 239000000843 powder Substances 0.000 description 5
- 239000002244 precipitate Substances 0.000 description 5
- ARBXWBKHEXLXFI-UHFFFAOYSA-N 9H-thioxanthene-4-carbaldehyde Chemical compound C1=CC=C(C=2SC3=CC=CC=C3CC12)C=O ARBXWBKHEXLXFI-UHFFFAOYSA-N 0.000 description 4
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- BEFDCLMNVWHSGT-UHFFFAOYSA-N ethenylcyclopentane Chemical compound C=CC1CCCC1 BEFDCLMNVWHSGT-UHFFFAOYSA-N 0.000 description 1
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- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 1
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- HNQIVZYLYMDVSB-UHFFFAOYSA-N methanesulfonimidic acid Chemical compound CS(N)(=O)=O HNQIVZYLYMDVSB-UHFFFAOYSA-N 0.000 description 1
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- SFDBHPJUOZSMJY-UHFFFAOYSA-N n-[[1-[2-(diethylamino)ethylamino]-9-oxothioxanthen-4-yl]methyl]formamide Chemical compound S1C2=CC=CC=C2C(=O)C2=C1C(CNC=O)=CC=C2NCCN(CC)CC SFDBHPJUOZSMJY-UHFFFAOYSA-N 0.000 description 1
- UHNHTTIUNATJKL-UHFFFAOYSA-N n-methylmethanesulfonamide Chemical compound CNS(C)(=O)=O UHNHTTIUNATJKL-UHFFFAOYSA-N 0.000 description 1
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- 231100000252 nontoxic Toxicity 0.000 description 1
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- 150000007524 organic acids Chemical class 0.000 description 1
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- 150000002895 organic esters Chemical class 0.000 description 1
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- 239000012188 paraffin wax Substances 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 229960003742 phenol Drugs 0.000 description 1
- 229920005862 polyol Polymers 0.000 description 1
- 150000003077 polyols Chemical class 0.000 description 1
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 1
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
- 230000003389 potentiating effect Effects 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
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- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 150000003856 quaternary ammonium compounds Chemical class 0.000 description 1
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- 150000004760 silicates Chemical class 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000001509 sodium citrate Substances 0.000 description 1
- NLJMYIDDQXHKNR-UHFFFAOYSA-K sodium citrate Chemical compound O.O.[Na+].[Na+].[Na+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O NLJMYIDDQXHKNR-UHFFFAOYSA-K 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 235000019333 sodium laurylsulphate Nutrition 0.000 description 1
- 239000004334 sorbic acid Substances 0.000 description 1
- 235000010199 sorbic acid Nutrition 0.000 description 1
- 229940075582 sorbic acid Drugs 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 235000000346 sugar Nutrition 0.000 description 1
- 150000008163 sugars Chemical class 0.000 description 1
- 229940124530 sulfonamide Drugs 0.000 description 1
- 150000003456 sulfonamides Chemical class 0.000 description 1
- 230000006103 sulfonylation Effects 0.000 description 1
- 238000005694 sulfonylation reaction Methods 0.000 description 1
- 235000011149 sulphuric acid Nutrition 0.000 description 1
- 239000004094 surface-active agent Substances 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
- 238000012360 testing method Methods 0.000 description 1
- 238000011200 topical administration Methods 0.000 description 1
- 231100000816 toxic dose Toxicity 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
- KHPCPRHQVVSZAH-UHFFFAOYSA-N trans-cinnamyl beta-D-glucopyranoside Natural products OC1C(O)C(O)C(CO)OC1OCC=CC1=CC=CC=C1 KHPCPRHQVVSZAH-UHFFFAOYSA-N 0.000 description 1
- 238000000870 ultraviolet spectroscopy Methods 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 230000004580 weight loss Effects 0.000 description 1
- 238000009736 wetting Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/6553—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having sulfur atoms, with or without selenium or tellurium atoms, as the only ring hetero atoms
- C07F9/655363—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having sulfur atoms, with or without selenium or tellurium atoms, as the only ring hetero atoms the sulfur atom being part of a six-membered ring
- C07F9/655372—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having sulfur atoms, with or without selenium or tellurium atoms, as the only ring hetero atoms the sulfur atom being part of a six-membered ring condensed with carbocyclic rings or carbocyclic ring systems
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D335/00—Heterocyclic compounds containing six-membered rings having one sulfur atom as the only ring hetero atom
- C07D335/04—Heterocyclic compounds containing six-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
- C07D335/10—Dibenzothiopyrans; Hydrogenated dibenzothiopyrans
- C07D335/12—Thioxanthenes
- C07D335/14—Thioxanthenes 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 in position 9
- C07D335/16—Oxygen atoms, e.g. thioxanthones
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Molecular Biology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Biochemistry (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US71317391A | 1991-06-10 | 1991-06-10 | |
| US71317391 | 1991-06-10 | ||
| US83515992A | 1992-02-13 | 1992-02-13 | |
| US83515992 | 1992-02-13 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| FI922694A0 FI922694A0 (fi) | 1992-06-10 |
| FI922694A FI922694A (fi) | 1992-12-11 |
| FI114024B true FI114024B (fi) | 2004-07-30 |
Family
ID=27108950
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FI922694A FI114024B (fi) | 1991-06-10 | 1992-06-10 | Menetelmä terapeuttisesti käyttökelpoisten tioksantenonijohdannaisten valmistamiseksi |
Country Status (20)
| Country | Link |
|---|---|
| EP (1) | EP0518414B1 (ko) |
| JP (1) | JP3045354B2 (ko) |
| KR (1) | KR100209826B1 (ko) |
| AT (1) | ATE106882T1 (ko) |
| AU (1) | AU642596B2 (ko) |
| CA (1) | CA2070120C (ko) |
| DE (1) | DE69200179T2 (ko) |
| DK (1) | DK0518414T3 (ko) |
| ES (1) | ES2055635T3 (ko) |
| FI (1) | FI114024B (ko) |
| HU (1) | HU218655B (ko) |
| IE (1) | IE66828B1 (ko) |
| IL (1) | IL102139A (ko) |
| MX (1) | MX9202753A (ko) |
| NO (1) | NO302364B1 (ko) |
| NZ (1) | NZ242862A (ko) |
| PH (1) | PH30883A (ko) |
| RU (1) | RU2075477C1 (ko) |
| SG (1) | SG50625A1 (ko) |
| TW (1) | TW218015B (ko) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5346917A (en) * | 1991-06-10 | 1994-09-13 | Sterling Winthrop Inc. | Thioxanthenone antitumor agents |
| US5091410A (en) * | 1991-06-10 | 1992-02-25 | Sterling Winthrop Inc. | Thioxanthenone antitumor agents |
| US5665760A (en) * | 1995-09-18 | 1997-09-09 | Sanofi Winthrop, Inc. | Lyophilized thioxanthenone antitumor agents |
| CA2695203A1 (en) * | 2007-07-31 | 2009-02-05 | University Of North Dakota Research Foundation | Improved method for the synthesis of substituted formylamines and substituted amines |
| FR2979823B1 (fr) * | 2011-09-13 | 2013-09-27 | Pf Medicament | Utilisation du 3-(r)-[3-(2-methoxyphenylthio)-2-(s)-methyl-propyl]amino-3,4-dihydro-2h-1,5-benzoxathiepine pour le traitement du cancer et en particulier pour la prevention et/ou le traitement des metastases cancereuses |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3745172A (en) * | 1970-10-05 | 1973-07-10 | Sterling Drug Inc | 1-(di-(lower-alkyl)aminoalkylamino)-9-oxothioxanthenes |
| US4539412A (en) * | 1982-07-08 | 1985-09-03 | Rensselaer Polytechnic Institute | 7-Hydroxylucanthone, 7-hydroxhycanthone and their analogs |
| US5091410A (en) * | 1991-06-10 | 1992-02-25 | Sterling Winthrop Inc. | Thioxanthenone antitumor agents |
-
1992
- 1992-05-21 AU AU17046/92A patent/AU642596B2/en not_active Ceased
- 1992-05-22 NZ NZ242862A patent/NZ242862A/xx not_active IP Right Cessation
- 1992-06-01 CA CA002070120A patent/CA2070120C/en not_active Expired - Fee Related
- 1992-06-03 TW TW081104387A patent/TW218015B/zh active
- 1992-06-03 EP EP92201587A patent/EP0518414B1/en not_active Expired - Lifetime
- 1992-06-03 AT AT92201587T patent/ATE106882T1/de not_active IP Right Cessation
- 1992-06-03 SG SG1996007125A patent/SG50625A1/en unknown
- 1992-06-03 DE DE69200179T patent/DE69200179T2/de not_active Expired - Fee Related
- 1992-06-03 ES ES92201587T patent/ES2055635T3/es not_active Expired - Lifetime
- 1992-06-03 DK DK92201587.0T patent/DK0518414T3/da active
- 1992-06-08 JP JP4147101A patent/JP3045354B2/ja not_active Expired - Fee Related
- 1992-06-09 KR KR1019920009956A patent/KR100209826B1/ko not_active IP Right Cessation
- 1992-06-09 RU SU925052026A patent/RU2075477C1/ru not_active IP Right Cessation
- 1992-06-09 IL IL102139A patent/IL102139A/xx not_active IP Right Cessation
- 1992-06-09 MX MX9202753A patent/MX9202753A/es not_active IP Right Cessation
- 1992-06-10 NO NO922273A patent/NO302364B1/no unknown
- 1992-06-10 FI FI922694A patent/FI114024B/fi not_active IP Right Cessation
- 1992-06-10 PH PH44488A patent/PH30883A/en unknown
- 1992-06-10 HU HU9201926A patent/HU218655B/hu not_active IP Right Cessation
- 1992-07-01 IE IE921871A patent/IE66828B1/en not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| EP0518414B1 (en) | 1994-06-08 |
| JPH05178853A (ja) | 1993-07-20 |
| TW218015B (ko) | 1993-12-21 |
| IE66828B1 (en) | 1996-02-07 |
| NZ242862A (en) | 1993-09-27 |
| IL102139A (en) | 1997-03-18 |
| CA2070120C (en) | 2005-11-15 |
| IL102139A0 (en) | 1993-01-14 |
| ATE106882T1 (de) | 1994-06-15 |
| FI922694A (fi) | 1992-12-11 |
| FI922694A0 (fi) | 1992-06-10 |
| KR100209826B1 (ko) | 1999-07-15 |
| AU1704692A (en) | 1992-12-17 |
| NO302364B1 (no) | 1998-02-23 |
| HU9201926D0 (en) | 1992-08-28 |
| MX9202753A (es) | 1993-01-01 |
| DK0518414T3 (da) | 1994-08-15 |
| KR930000499A (ko) | 1993-01-15 |
| CA2070120A1 (en) | 1992-12-11 |
| HU218655B (hu) | 2000-10-28 |
| IE921871A1 (en) | 1992-12-16 |
| RU2075477C1 (ru) | 1997-03-20 |
| JP3045354B2 (ja) | 2000-05-29 |
| AU642596B2 (en) | 1993-10-21 |
| EP0518414A1 (en) | 1992-12-16 |
| DE69200179D1 (de) | 1994-07-14 |
| ES2055635T3 (es) | 1994-08-16 |
| DE69200179T2 (de) | 1995-01-19 |
| SG50625A1 (en) | 1998-07-20 |
| NO922273L (no) | 1992-12-11 |
| PH30883A (en) | 1997-12-23 |
| NO922273D0 (no) | 1992-06-10 |
| HUT61992A (en) | 1993-03-29 |
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