IL27086A - History 4 - ('5 - Nitro - Porforyldine - Emino) - Tetrahydro 1, 4 - Thiazine 1, 1 - Dioxide and their preparation - Google Patents
History 4 - ('5 - Nitro - Porforyldine - Emino) - Tetrahydro 1, 4 - Thiazine 1, 1 - Dioxide and their preparationInfo
- Publication number
- IL27086A IL27086A IL6627086A IL2708666A IL27086A IL 27086 A IL27086 A IL 27086A IL 6627086 A IL6627086 A IL 6627086A IL 2708666 A IL2708666 A IL 2708666A IL 27086 A IL27086 A IL 27086A
- Authority
- IL
- Israel
- Prior art keywords
- dioxide
- thiazine
- tetrahydro
- imino
- methanol
- Prior art date
Links
- 238000002360 preparation method Methods 0.000 title claims description 3
- 150000001875 compounds Chemical class 0.000 claims description 10
- 208000015181 infectious disease Diseases 0.000 claims description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 3
- 238000000034 method Methods 0.000 claims description 2
- 239000004480 active ingredient Substances 0.000 claims 1
- 210000005056 cell body Anatomy 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 57
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 21
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 16
- 229910052739 hydrogen Inorganic materials 0.000 description 12
- 230000003647 oxidation Effects 0.000 description 8
- 238000007254 oxidation reaction Methods 0.000 description 8
- 238000001953 recrystallisation Methods 0.000 description 8
- 229910052717 sulfur Inorganic materials 0.000 description 8
- NWZSZGALRFJKBT-KNIFDHDWSA-N (2s)-2,6-diaminohexanoic acid;(2s)-2-hydroxybutanedioic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O.NCCCC[C@H](N)C(O)=O NWZSZGALRFJKBT-KNIFDHDWSA-N 0.000 description 7
- 238000006243 chemical reaction Methods 0.000 description 7
- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 7
- 238000006798 ring closing metathesis reaction Methods 0.000 description 7
- DGVVWUTYPXICAM-UHFFFAOYSA-N β‐Mercaptoethanol Chemical compound OCCS DGVVWUTYPXICAM-UHFFFAOYSA-N 0.000 description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- 241000283690 Bos taurus Species 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- 230000000694 effects Effects 0.000 description 6
- 239000007858 starting material Substances 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- 238000009835 boiling Methods 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- 241001465754 Metazoa Species 0.000 description 4
- 241000223104 Trypanosoma Species 0.000 description 4
- 239000013078 crystal Substances 0.000 description 4
- DNJIEGIFACGWOD-UHFFFAOYSA-N ethyl mercaptane Natural products CCS DNJIEGIFACGWOD-UHFFFAOYSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 229960000583 acetic acid Drugs 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 239000012362 glacial acetic acid Substances 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- KQXZMAACKJIRJE-UHFFFAOYSA-N 2-(2-methoxyethoxymethyl)oxirane Chemical compound COCCOCC1CO1 KQXZMAACKJIRJE-UHFFFAOYSA-N 0.000 description 2
- LKMJVFRMDSNFRT-UHFFFAOYSA-N 2-(methoxymethyl)oxirane Chemical compound COCC1CO1 LKMJVFRMDSNFRT-UHFFFAOYSA-N 0.000 description 2
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 2
- MESFXNGUDNODTJ-UHFFFAOYSA-N 2h-thiazine 1,1-dioxide Chemical compound O=S1(=O)NC=CC=C1 MESFXNGUDNODTJ-UHFFFAOYSA-N 0.000 description 2
- 206010001935 American trypanosomiasis Diseases 0.000 description 2
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 2
- 241000699670 Mus sp. Species 0.000 description 2
- UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 description 2
- 241000223109 Trypanosoma cruzi Species 0.000 description 2
- 239000008280 blood Substances 0.000 description 2
- 210000004369 blood Anatomy 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 2
- 150000002500 ions Chemical class 0.000 description 2
- -1 methoxyethyl group Chemical group 0.000 description 2
- 239000001294 propane Substances 0.000 description 2
- WWRUZECKUVNAPB-UHFFFAOYSA-N 1,4-oxathiane 4,4-dioxide Chemical class O=S1(=O)CCOCC1 WWRUZECKUVNAPB-UHFFFAOYSA-N 0.000 description 1
- NDOVLWQBFFJETK-UHFFFAOYSA-N 1,4-thiazinane 1,1-dioxide Chemical compound O=S1(=O)CCNCC1 NDOVLWQBFFJETK-UHFFFAOYSA-N 0.000 description 1
- ORGQUCCTTDAMOK-UHFFFAOYSA-N 1-methoxy-3-sulfanylpropan-2-ol Chemical compound COCC(O)CS ORGQUCCTTDAMOK-UHFFFAOYSA-N 0.000 description 1
- PJOUFZLECMLIAX-UHFFFAOYSA-N 2-(butylsulfanylmethyl)oxirane Chemical compound CCCCSCC1CO1 PJOUFZLECMLIAX-UHFFFAOYSA-N 0.000 description 1
- HQCSZRIVJVOYSU-UHFFFAOYSA-N 2-(ethoxymethyl)oxirane Chemical compound CCOCC1CO1 HQCSZRIVJVOYSU-UHFFFAOYSA-N 0.000 description 1
- LSWYGACWGAICNM-UHFFFAOYSA-N 2-(prop-2-enoxymethyl)oxirane Chemical compound C=CCOCC1CO1 LSWYGACWGAICNM-UHFFFAOYSA-N 0.000 description 1
- SXINBFXPADXIEY-UHFFFAOYSA-N 5-Nitrofurfural Chemical compound [O-][N+](=O)C1=CC=C(C=O)O1 SXINBFXPADXIEY-UHFFFAOYSA-N 0.000 description 1
- 208000024699 Chagas disease Diseases 0.000 description 1
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 1
- FQYUMYWMJTYZTK-UHFFFAOYSA-N Phenyl glycidyl ether Chemical compound C1OC1COC1=CC=CC=C1 FQYUMYWMJTYZTK-UHFFFAOYSA-N 0.000 description 1
- 241000220010 Rhode Species 0.000 description 1
- 241000223107 Trypanosoma congolense Species 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 125000003342 alkenyl group Chemical group 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 230000015572 biosynthetic process Effects 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
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 230000035876 healing Effects 0.000 description 1
- 150000007857 hydrazones Chemical class 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 231100000053 low toxicity Toxicity 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 231100000682 maximum tolerated dose Toxicity 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 150000002923 oximes Chemical class 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- KOUKXHPPRFNWPP-UHFFFAOYSA-N pyrazine-2,5-dicarboxylic acid;hydrate Chemical compound O.OC(=O)C1=CN=C(C(O)=O)C=N1 KOUKXHPPRFNWPP-UHFFFAOYSA-N 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000011877 solvent mixture Substances 0.000 description 1
- 230000002269 spontaneous effect Effects 0.000 description 1
- 238000000967 suction filtration Methods 0.000 description 1
- 125000001174 sulfone group Chemical group 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 231100001274 therapeutic index Toxicity 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D327/00—Heterocyclic compounds containing rings having oxygen and sulfur atoms as the only ring hetero atoms
- C07D327/02—Heterocyclic compounds containing rings having oxygen and sulfur atoms as the only ring hetero atoms one oxygen atom and one sulfur atom
- C07D327/06—Six-membered rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D303/00—Compounds containing three-membered rings having one oxygen atom as the only ring hetero atom
- C07D303/02—Compounds containing oxirane rings
- C07D303/12—Compounds containing oxirane rings with hydrocarbon radicals, substituted by singly or doubly bound oxygen atoms
- C07D303/18—Compounds containing oxirane rings with hydrocarbon radicals, substituted by singly or doubly bound oxygen atoms by etherified hydroxyl radicals
- C07D303/20—Ethers with hydroxy compounds containing no oxirane rings
- C07D303/24—Ethers with hydroxy compounds containing no oxirane rings with polyhydroxy compounds
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen- Or Sulfur-Containing Heterocyclic Ring Compounds With Rings Of Six Or More Members (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEF0048092 | 1966-01-05 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| IL27086A true IL27086A (en) | 1970-06-17 |
Family
ID=7102036
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IL6627086A IL27086A (en) | 1966-01-05 | 1966-12-19 | History 4 - ('5 - Nitro - Porforyldine - Emino) - Tetrahydro 1, 4 - Thiazine 1, 1 - Dioxide and their preparation |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US3488348A (de) |
| CH (1) | CH472429A (de) |
| DE (1) | DE1670657C3 (de) |
| FR (1) | FR1507525A (de) |
| GB (1) | GB1120652A (de) |
| IL (1) | IL27086A (de) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1670840A1 (de) * | 1967-03-31 | 1971-03-11 | Bayer Ag | Verfahren zur Herstellung von Tetra-hydro-1,4-thiazin-1,1-dioxiden |
| US7049472B2 (en) | 2004-07-26 | 2006-05-23 | Air Products And Chemicals, Inc. | Bis(3-alkoxyalkan-2-OL) sulfides, sulfones, and sulfoxides: new surface active agents |
| US7205431B2 (en) | 2004-07-26 | 2007-04-17 | Air Products And Chemicals, Inc. | Bis(3-alkoxyalkan-2-ol) sulfides, sulfones, and sulfoxides: new surface active agents |
| US7341985B2 (en) | 2004-10-08 | 2008-03-11 | Air Products And Chemicals, Inc. | 2-Hydroxy-3-alkoxypropyl sulfides, sulfones, and sulfoxides: new surface active agents |
| FR3005050A1 (fr) * | 2013-04-26 | 2014-10-31 | Michelin & Cie | Compose polyol soufre utilisable comme monomere pour la synthese de polyurethane |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1170957B (de) * | 1962-11-23 | 1964-05-27 | Bayer Ag | Verfahren zur Herstellung von 5-Nitro-furfuryliden-(2)-iminoderivaten |
-
1966
- 1966-01-05 DE DE1670657A patent/DE1670657C3/de not_active Expired
- 1966-12-07 CH CH1753966A patent/CH472429A/de not_active IP Right Cessation
- 1966-12-19 IL IL6627086A patent/IL27086A/en unknown
- 1966-12-23 US US604172A patent/US3488348A/en not_active Expired - Lifetime
-
1967
- 1967-01-05 GB GB753/67A patent/GB1120652A/en not_active Expired
- 1967-01-05 FR FR90070A patent/FR1507525A/fr not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| DE1670657C3 (de) | 1975-01-23 |
| GB1120652A (en) | 1968-07-24 |
| CH472429A (de) | 1969-05-15 |
| DE1670657A1 (de) | 1970-12-03 |
| FR1507525A (fr) | 1967-12-29 |
| DE1670657B2 (de) | 1974-06-12 |
| US3488348A (en) | 1970-01-06 |
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