SU416947A3 - Способ получения ацилоксиалкилгетероцикли-ческих соединений - Google Patents
Способ получения ацилоксиалкилгетероцикли-ческих соединенийInfo
- Publication number
- SU416947A3 SU416947A3 SU1620557A SU1620557A SU416947A3 SU 416947 A3 SU416947 A3 SU 416947A3 SU 1620557 A SU1620557 A SU 1620557A SU 1620557 A SU1620557 A SU 1620557A SU 416947 A3 SU416947 A3 SU 416947A3
- Authority
- SU
- USSR - Soviet Union
- Prior art keywords
- carbonylmethyl
- piperazinyl
- chloro
- heterocyclic compounds
- benzothiazolinone
- Prior art date
Links
- 238000000034 method Methods 0.000 title description 8
- 150000002391 heterocyclic compounds Chemical class 0.000 title description 2
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 15
- -1 acyloxyalkyl heterocyclic compounds Chemical class 0.000 description 10
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
- 239000013078 crystal Substances 0.000 description 7
- 150000001875 compounds Chemical class 0.000 description 6
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 6
- 150000003839 salts Chemical class 0.000 description 6
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- 238000000354 decomposition reaction Methods 0.000 description 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- 150000001408 amides Chemical class 0.000 description 3
- 125000005843 halogen group Chemical group 0.000 description 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- 229920000388 Polyphosphate Polymers 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 150000008065 acid anhydrides Chemical class 0.000 description 2
- 125000003545 alkoxy group Chemical group 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- 125000002714 alpha-linolenoyl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])/C([H])=C([H])\C([H])([H])/C([H])=C([H])\C([H])([H])/C([H])=C([H])\C([H])([H])C([H])([H])[H] 0.000 description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 2
- 230000004071 biological effect Effects 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 229940125782 compound 2 Drugs 0.000 description 2
- 238000002955 isolation Methods 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- 239000001205 polyphosphate Substances 0.000 description 2
- 235000011176 polyphosphates Nutrition 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 1
- FYKPDAJKYKYJSL-UHFFFAOYSA-N 2-(5-chloro-2-oxo-1,3-benzothiazol-3-yl)acetyl chloride Chemical compound ClC1=CC=C2SC(=O)N(CC(=O)Cl)C2=C1 FYKPDAJKYKYJSL-UHFFFAOYSA-N 0.000 description 1
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 1
- QJRURUUCKOJDCU-UHFFFAOYSA-N 2-[4-[2-(5-chloro-2-oxo-1,3-benzothiazol-3-yl)acetyl]piperazin-1-yl]ethyl 3,4,5-trimethoxybenzoate Chemical compound COC1=CC(=CC(OC)=C1OC)C(=O)OCCN1CCN(CC1)C(=O)CN1C(=O)SC2=CC=C(Cl)C=C12 QJRURUUCKOJDCU-UHFFFAOYSA-N 0.000 description 1
- HMOWAHCFKSZMGR-UHFFFAOYSA-N 2-[5-chloro-2-oxo-1-(2-oxo-2-piperazin-1-ylethyl)-3H-1,3-benzothiazol-1-yl]ethyl octadecanoate Chemical compound C(CCCCCCCCCCCCCCCCC)(=O)OCCS1(C(NC2=C1C=CC(=C2)Cl)=O)CC(=O)N1CCNCC1 HMOWAHCFKSZMGR-UHFFFAOYSA-N 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- DBYKARZMSYMGKB-UHFFFAOYSA-N C(=O)=CC1=C(C=CC2=C1NC(S2)=O)Cl Chemical compound C(=O)=CC1=C(C=CC2=C1NC(S2)=O)Cl DBYKARZMSYMGKB-UHFFFAOYSA-N 0.000 description 1
- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- 230000010933 acylation Effects 0.000 description 1
- 238000005917 acylation reaction Methods 0.000 description 1
- 229910000288 alkali metal carbonate Inorganic materials 0.000 description 1
- 150000008041 alkali metal carbonates Chemical class 0.000 description 1
- 125000005277 alkyl imino group Chemical group 0.000 description 1
- 125000002947 alkylene group Chemical group 0.000 description 1
- 125000001118 alkylidene group Chemical group 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- 125000001124 arachidoyl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 150000001540 azides Chemical class 0.000 description 1
- 229910000019 calcium carbonate Inorganic materials 0.000 description 1
- 125000001589 carboacyl group Chemical group 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 230000001747 exhibiting effect Effects 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 125000002669 linoleoyl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])/C([H])=C([H])\C([H])([H])/C([H])=C([H])\C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- 125000000628 margaroyl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- JYQQWQJCEUMXQZ-UHFFFAOYSA-N methyl cyanate Chemical compound COC#N JYQQWQJCEUMXQZ-UHFFFAOYSA-N 0.000 description 1
- 150000004702 methyl esters Chemical class 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 125000000896 monocarboxylic acid group Chemical group 0.000 description 1
- 125000001117 oleyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])/C([H])=C([H])\C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- 125000001312 palmitoyl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229920000137 polyphosphoric acid Polymers 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 125000003696 stearoyl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 125000005270 trialkylamine group Chemical group 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
- A61K31/425—Thiazoles
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Life Sciences & Earth Sciences (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)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2144869 | 1969-03-20 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SU416947A3 true SU416947A3 (ru) | 1974-02-25 |
Family
ID=12055228
Family Applications (3)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SU1620557A SU416947A3 (ru) | 1969-03-20 | 1970-03-20 | Способ получения ацилоксиалкилгетероцикли-ческих соединений |
| SU1620554A SU400104A3 (enExample) | 1969-03-20 | 1970-03-20 | |
| SU1413002A SU420180A3 (ru) | 1969-03-20 | 1970-03-20 | Способ получения ацилоксиалкил- гетероциклических соединений |
Family Applications After (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SU1620554A SU400104A3 (enExample) | 1969-03-20 | 1970-03-20 | |
| SU1413002A SU420180A3 (ru) | 1969-03-20 | 1970-03-20 | Способ получения ацилоксиалкил- гетероциклических соединений |
Country Status (11)
| Country | Link |
|---|---|
| AT (1) | AT301539B (enExample) |
| BE (1) | BE747274R (enExample) |
| CH (3) | CH554363A (enExample) |
| DE (1) | DE2012667C3 (enExample) |
| DK (1) | DK134023B (enExample) |
| ES (4) | ES377689A1 (enExample) |
| FI (1) | FI52088C (enExample) |
| NL (1) | NL7004067A (enExample) |
| NO (1) | NO128822B (enExample) |
| SE (1) | SE360869B (enExample) |
| SU (3) | SU416947A3 (enExample) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GR65270B (en) * | 1978-10-10 | 1980-07-31 | Fujisawa Pharmaceutical Co | Isatin derivatives and processes for the preparation thereof |
| US4411900A (en) * | 1980-01-03 | 1983-10-25 | Fujisawa Pharmaceutical Co., Ltd. | Benzhydrylpiperozinyl thiazole derivatives and pharmaceutical composition comprising the same |
| FR2637286A1 (fr) * | 1988-10-04 | 1990-04-06 | Adir | Nouveaux derives benzoxazolinoniques, leurs procedes de preparation et les compositions pharmaceutiques qui les contiennent |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NL244642A (enExample) * | 1958-10-29 |
-
1970
- 1970-03-12 BE BE747274D patent/BE747274R/xx active
- 1970-03-13 FI FI68870A patent/FI52088C/fi active
- 1970-03-17 DE DE19702012667 patent/DE2012667C3/de not_active Expired
- 1970-03-18 ES ES377689A patent/ES377689A1/es not_active Expired
- 1970-03-19 NO NO100670A patent/NO128822B/no unknown
- 1970-03-19 SE SE371670A patent/SE360869B/xx unknown
- 1970-03-19 AT AT259670A patent/AT301539B/de not_active IP Right Cessation
- 1970-03-20 CH CH1496673A patent/CH554363A/xx not_active IP Right Cessation
- 1970-03-20 NL NL7004067A patent/NL7004067A/xx not_active Application Discontinuation
- 1970-03-20 CH CH1496773A patent/CH554364A/xx not_active IP Right Cessation
- 1970-03-20 SU SU1620557A patent/SU416947A3/ru active
- 1970-03-20 SU SU1620554A patent/SU400104A3/ru active
- 1970-03-20 DK DK141070A patent/DK134023B/da unknown
- 1970-03-20 CH CH427470A patent/CH565174A5/xx not_active IP Right Cessation
- 1970-03-20 SU SU1413002A patent/SU420180A3/ru active
-
1972
- 1972-09-01 ES ES406296A patent/ES406296A1/es not_active Expired
- 1972-09-01 ES ES406297A patent/ES406297A1/es not_active Expired
- 1972-09-01 ES ES406298A patent/ES406298A1/es not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| ES406297A1 (es) | 1975-09-16 |
| FI52088C (fi) | 1977-06-10 |
| NL7004067A (enExample) | 1970-09-22 |
| DE2012667A1 (de) | 1970-10-01 |
| BE747274R (fr) | 1970-08-17 |
| CH554364A (de) | 1974-09-30 |
| SE360869B (enExample) | 1973-10-08 |
| ES377689A1 (es) | 1973-01-01 |
| SU400104A3 (enExample) | 1973-10-03 |
| DE2012667C3 (de) | 1981-11-26 |
| CH554363A (de) | 1974-09-30 |
| ES406298A1 (es) | 1975-09-16 |
| ES406296A1 (es) | 1975-09-16 |
| FI52088B (enExample) | 1977-02-28 |
| DE2012667B2 (de) | 1981-02-26 |
| DK134023C (enExample) | 1977-03-21 |
| SU420180A3 (ru) | 1974-03-15 |
| NO128822B (enExample) | 1974-01-14 |
| AT301539B (de) | 1972-09-11 |
| DK134023B (da) | 1976-08-30 |
| CH565174A5 (enExample) | 1975-08-15 |
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