PL105486B1 - Sposob wytwarzania nowych estrowych pochodnych tiazolinylo i tiazynylobenzimidazolu o dzialaniu przeciwwirusowym - Google Patents
Sposob wytwarzania nowych estrowych pochodnych tiazolinylo i tiazynylobenzimidazolu o dzialaniu przeciwwirusowym Download PDFInfo
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- PL105486B1 PL105486B1 PL1976192395A PL19239576A PL105486B1 PL 105486 B1 PL105486 B1 PL 105486B1 PL 1976192395 A PL1976192395 A PL 1976192395A PL 19239576 A PL19239576 A PL 19239576A PL 105486 B1 PL105486 B1 PL 105486B1
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- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
- GUDMZGLFZNLYEY-UHFFFAOYSA-N cyclopropylmethanol Chemical compound OCC1CC1 GUDMZGLFZNLYEY-UHFFFAOYSA-N 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 150000004985 diamines Chemical class 0.000 description 1
- 150000005690 diesters Chemical class 0.000 description 1
- 239000006196 drop Substances 0.000 description 1
- 239000003937 drug carrier Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000009977 dual effect Effects 0.000 description 1
- 239000000428 dust Substances 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- HHFAWKCIHAUFRX-UHFFFAOYSA-N ethoxide Chemical compound CC[O-] HHFAWKCIHAUFRX-UHFFFAOYSA-N 0.000 description 1
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 description 1
- 125000004494 ethyl ester group Chemical group 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 235000013312 flour Nutrition 0.000 description 1
- 239000006260 foam Substances 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- 238000005242 forging Methods 0.000 description 1
- 238000001640 fractional crystallisation Methods 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 239000000499 gel Substances 0.000 description 1
- 239000008273 gelatin Substances 0.000 description 1
- 229920000159 gelatin Polymers 0.000 description 1
- 235000019322 gelatine Nutrition 0.000 description 1
- 235000011852 gelatine desserts Nutrition 0.000 description 1
- 238000007429 general method Methods 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 230000009036 growth inhibition Effects 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 150000004678 hydrides Chemical class 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- 238000000338 in vitro Methods 0.000 description 1
- 230000000415 inactivating effect Effects 0.000 description 1
- 206010022000 influenza Diseases 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 239000012948 isocyanate Substances 0.000 description 1
- 150000002513 isocyanates Chemical class 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 1
- 229910052987 metal hydride Inorganic materials 0.000 description 1
- 150000004681 metal hydrides Chemical class 0.000 description 1
- 125000006431 methyl cyclopropyl group Chemical group 0.000 description 1
- 238000001000 micrograph Methods 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- CMWTZPSULFXXJA-VIFPVBQESA-N naproxen Chemical group C1=C([C@H](C)C(O)=O)C=CC2=CC(OC)=CC=C21 CMWTZPSULFXXJA-VIFPVBQESA-N 0.000 description 1
- 239000007923 nasal drop Substances 0.000 description 1
- 229940100662 nasal drops Drugs 0.000 description 1
- 239000007922 nasal spray Substances 0.000 description 1
- 229940097496 nasal spray Drugs 0.000 description 1
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 125000003431 oxalo group Chemical group 0.000 description 1
- 229940049954 penicillin Drugs 0.000 description 1
- 239000012466 permeate Substances 0.000 description 1
- 239000008024 pharmaceutical diluent Substances 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 229910000105 potassium hydride Inorganic materials 0.000 description 1
- NTTOTNSKUYCDAV-UHFFFAOYSA-N potassium hydride Chemical compound [KH] NTTOTNSKUYCDAV-UHFFFAOYSA-N 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 229940002612 prodrug Drugs 0.000 description 1
- 239000000651 prodrug Substances 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 239000013049 sediment Substances 0.000 description 1
- 239000004460 silage Substances 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 235000015424 sodium Nutrition 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- ODZPKZBBUMBTMG-UHFFFAOYSA-N sodium amide Chemical compound [NH2-].[Na+] ODZPKZBBUMBTMG-UHFFFAOYSA-N 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 230000002459 sustained effect Effects 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 150000003549 thiazolines Chemical class 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
- 208000011479 upper respiratory tract disease Diseases 0.000 description 1
- 229960005486 vaccine Drugs 0.000 description 1
- 230000003612 virological effect Effects 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C205/00—Compounds containing nitro groups bound to a carbon skeleton
- C07C205/49—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by carboxyl groups
- C07C205/57—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by carboxyl groups having nitro groups and carboxyl groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/12—Antivirals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D235/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings
- C07D235/02—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings condensed with carbocyclic rings or ring systems
- C07D235/04—Benzimidazoles; Hydrogenated benzimidazoles
- C07D235/24—Benzimidazoles; Hydrogenated benzimidazoles 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 2
- C07D235/30—Nitrogen atoms not forming part of a nitro radical
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Oncology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Virology (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Communicable Diseases (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US05/633,203 US4008243A (en) | 1975-11-19 | 1975-11-19 | Antiviral thiazolinyl or thiazinyl benzimidazole esters |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| PL105486B1 true PL105486B1 (pl) | 1979-10-31 |
Family
ID=24538665
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PL1976192395A PL105486B1 (pl) | 1975-11-19 | 1976-09-14 | Sposob wytwarzania nowych estrowych pochodnych tiazolinylo i tiazynylobenzimidazolu o dzialaniu przeciwwirusowym |
| PL1976210940A PL110781B1 (en) | 1975-11-19 | 1976-09-14 | Method of producing new ester derivatives of thiazolinylo-and thiazynylobenzimidazole with anti-virus activity |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PL1976210940A PL110781B1 (en) | 1975-11-19 | 1976-09-14 | Method of producing new ester derivatives of thiazolinylo-and thiazynylobenzimidazole with anti-virus activity |
Country Status (30)
| Country | Link |
|---|---|
| US (1) | US4008243A (en, 2012) |
| JP (1) | JPS5265269A (en, 2012) |
| AR (1) | AR218228A1 (en, 2012) |
| AT (1) | AT358029B (en, 2012) |
| AU (1) | AU498521B2 (en, 2012) |
| BE (1) | BE845643A (en, 2012) |
| BG (1) | BG27550A3 (en, 2012) |
| CA (1) | CA1059510A (en, 2012) |
| CH (1) | CH623052A5 (en, 2012) |
| CS (1) | CS199280B2 (en, 2012) |
| DD (1) | DD128675A5 (en, 2012) |
| DE (1) | DE2638552A1 (en, 2012) |
| DK (1) | DK142813B (en, 2012) |
| ES (2) | ES451020A1 (en, 2012) |
| FR (1) | FR2332011A1 (en, 2012) |
| GB (1) | GB1561481A (en, 2012) |
| GR (1) | GR61722B (en, 2012) |
| HU (1) | HU172633B (en, 2012) |
| IE (1) | IE43618B1 (en, 2012) |
| IL (1) | IL50294A (en, 2012) |
| MX (1) | MX4067E (en, 2012) |
| NL (1) | NL7609415A (en, 2012) |
| NZ (1) | NZ181788A (en, 2012) |
| PH (1) | PH13615A (en, 2012) |
| PL (2) | PL105486B1 (en, 2012) |
| PT (1) | PT65488B (en, 2012) |
| RO (1) | RO72653A (en, 2012) |
| SU (1) | SU721003A3 (en, 2012) |
| YU (1) | YU203576A (en, 2012) |
| ZA (1) | ZA765143B (en, 2012) |
Families Citing this family (18)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA1076582A (en) * | 1975-10-28 | 1980-04-29 | Charles J. Paget | Antiviral thiazolinyl or thiazinyl ketobenzimidazoles |
| US4293558A (en) * | 1975-10-28 | 1981-10-06 | Eli Lilly And Company | Antiviral thiazolinyl benzimidazoles and derivatives |
| US4191832A (en) * | 1979-03-12 | 1980-03-04 | Eli Lilly And Company | Separation of syn and anti oximes of 1-sulfonyl-2-aminobenzimidazoles |
| US4338315A (en) * | 1979-11-14 | 1982-07-06 | Eli Lilly And Company | Antiviral method employing thiazinyl benzimidazole derivatives |
| US4401817A (en) * | 1981-04-20 | 1983-08-30 | Eli Lilly And Company | Carbonyl-substituted 1-sulfonylbenzimidazoles |
| US4420479A (en) * | 1982-04-08 | 1983-12-13 | Eli Lilly And Company | Olefinic benzimidazoles, formulations, and antiviral methods |
| IL68297A (en) * | 1982-04-08 | 1986-09-30 | Lilly Co Eli | Process for removing 1-sulfonyl groups from 2-amino-5(6)-substituted benzimidazoles |
| US4463181A (en) * | 1982-04-08 | 1984-07-31 | Eli Lilly And Company | Process for removing sulfonyl groups from benzimidazole isomers |
| US4434288A (en) | 1982-04-08 | 1984-02-28 | Eli Lilly And Company | Preparation of substituted 1-thiazinyl or 1-thiazolyl-2-aminobenzimidazoles |
| US4492708A (en) * | 1982-09-27 | 1985-01-08 | Eli Lilly And Company | Antiviral benzimidazoles |
| US5508594A (en) * | 1994-06-10 | 1996-04-16 | Westinghouse Electric Corp | Electric vehicle chassis controller |
| US6358971B1 (en) | 1998-05-20 | 2002-03-19 | Eli Lilly And Company | Anti-viral compounds |
| WO2008021338A2 (en) * | 2006-08-15 | 2008-02-21 | Wyeth | Tricyclic oxazolidone derivatives useful as pr modulators |
| TW200815428A (en) * | 2006-08-15 | 2008-04-01 | Wyeth Corp | Oxazolidone derivatives as PR modulators |
| US7649007B2 (en) * | 2006-08-15 | 2010-01-19 | Wyeth Llc | Oxazolidine derivatives as PR modulators |
| US20080045560A1 (en) * | 2006-08-15 | 2008-02-21 | Wyeth | Pyrrolidine and related derivatives useful as PR modulators |
| US7652018B2 (en) * | 2006-08-15 | 2010-01-26 | Wyeth Llc | Imidazolidin-2-one derivatives useful as PR modulators |
| US7538107B2 (en) | 2006-08-15 | 2009-05-26 | Wyeth | Oxazinan-2-one derivatives useful as PR modulators |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3749717A (en) * | 1971-05-04 | 1973-07-31 | Squibb & Sons Inc | Thiazolinyl and thiazinyl derivatives of benzimidazoles |
| US3825537A (en) * | 1972-02-28 | 1974-07-23 | Squibb & Sons Inc | 1-thiazolin-2-yl(or thiazin-2-yl)-2-aminobenzimidazoles and derivatives thereof |
| US3833574A (en) * | 1972-07-31 | 1974-09-03 | Squibb & Sons Inc | Benzimidazolinone compounds |
-
1975
- 1975-11-19 US US05/633,203 patent/US4008243A/en not_active Expired - Lifetime
-
1976
- 1976-08-17 PT PT65488A patent/PT65488B/pt unknown
- 1976-08-17 NZ NZ181788A patent/NZ181788A/xx unknown
- 1976-08-17 GR GR51490A patent/GR61722B/el unknown
- 1976-08-17 MX MX763669U patent/MX4067E/es unknown
- 1976-08-18 HU HU76EI00000693A patent/HU172633B/hu unknown
- 1976-08-18 IL IL50294A patent/IL50294A/xx unknown
- 1976-08-19 AU AU16984/76A patent/AU498521B2/en not_active Expired
- 1976-08-19 YU YU02035/76A patent/YU203576A/xx unknown
- 1976-08-19 AR AR264379A patent/AR218228A1/es active
- 1976-08-19 CA CA259,393A patent/CA1059510A/en not_active Expired
- 1976-08-20 PH PH18822A patent/PH13615A/en unknown
- 1976-08-24 CS CS765494A patent/CS199280B2/cs unknown
- 1976-08-24 NL NL7609415A patent/NL7609415A/xx not_active Application Discontinuation
- 1976-08-24 IE IE1883/76A patent/IE43618B1/en unknown
- 1976-08-24 GB GB35092/76A patent/GB1561481A/en not_active Expired
- 1976-08-25 RO RO7687361A patent/RO72653A/ro unknown
- 1976-08-26 DE DE19762638552 patent/DE2638552A1/de not_active Withdrawn
- 1976-08-26 DK DK386276AA patent/DK142813B/da not_active IP Right Cessation
- 1976-08-26 SU SU762390302A patent/SU721003A3/ru active
- 1976-08-26 CH CH1085676A patent/CH623052A5/de not_active IP Right Cessation
- 1976-08-26 ES ES451020A patent/ES451020A1/es not_active Expired
- 1976-08-26 BG BG034082A patent/BG27550A3/xx unknown
- 1976-08-26 AT AT636576A patent/AT358029B/de not_active IP Right Cessation
- 1976-08-27 BE BE1007588A patent/BE845643A/xx not_active IP Right Cessation
- 1976-08-27 DD DD7600194504A patent/DD128675A5/xx unknown
- 1976-08-27 FR FR7626028A patent/FR2332011A1/fr active Granted
- 1976-08-27 ZA ZA00765143A patent/ZA765143B/xx unknown
- 1976-09-14 PL PL1976192395A patent/PL105486B1/pl unknown
- 1976-09-14 PL PL1976210940A patent/PL110781B1/pl unknown
- 1976-11-17 JP JP51139043A patent/JPS5265269A/ja active Pending
-
1977
- 1977-08-16 ES ES461632A patent/ES461632A1/es not_active Expired
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