CS200494B2 - Process for preparing therapeutical acylaminosubstituted five-memberd heterocyclic compounds - Google Patents
Process for preparing therapeutical acylaminosubstituted five-memberd heterocyclic compounds Download PDFInfo
- Publication number
- CS200494B2 CS200494B2 CS763692A CS369276A CS200494B2 CS 200494 B2 CS200494 B2 CS 200494B2 CS 763692 A CS763692 A CS 763692A CS 369276 A CS369276 A CS 369276A CS 200494 B2 CS200494 B2 CS 200494B2
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- CS
- Czechoslovakia
- Prior art keywords
- methyl
- group
- substituted
- compound
- formula
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- 150000002391 heterocyclic compounds Chemical class 0.000 title claims description 3
- 230000001225 therapeutic effect Effects 0.000 title description 6
- 238000004519 manufacturing process Methods 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims abstract description 62
- 238000000034 method Methods 0.000 claims abstract description 14
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 13
- 125000005842 heteroatom Chemical group 0.000 claims abstract description 6
- 125000001072 heteroaryl group Chemical group 0.000 claims abstract description 5
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 4
- 125000004433 nitrogen atom Chemical group N* 0.000 claims abstract description 4
- 239000001301 oxygen Substances 0.000 claims abstract description 4
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims abstract description 3
- 229910052799 carbon Inorganic materials 0.000 claims description 40
- 229910052739 hydrogen Inorganic materials 0.000 claims description 34
- 125000000217 alkyl group Chemical group 0.000 claims description 13
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 11
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 11
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 8
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 7
- 238000002360 preparation method Methods 0.000 claims description 7
- 239000001257 hydrogen Substances 0.000 claims description 6
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- 229910052801 chlorine Inorganic materials 0.000 claims description 4
- 229910052736 halogen Inorganic materials 0.000 claims description 4
- 150000002367 halogens Chemical class 0.000 claims description 4
- 229910052717 sulfur Chemical group 0.000 claims description 4
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 3
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 3
- 229910052794 bromium Inorganic materials 0.000 claims description 3
- 125000000623 heterocyclic group Chemical group 0.000 claims description 3
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- DGEZNRSVGBDHLK-UHFFFAOYSA-N [1,10]phenanthroline Chemical compound C1=CN=C2C3=NC=CC=C3C=CC2=C1 DGEZNRSVGBDHLK-UHFFFAOYSA-N 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 2
- 239000011593 sulfur Chemical group 0.000 claims description 2
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- 238000009835 boiling Methods 0.000 description 26
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- 238000004440 column chromatography Methods 0.000 description 3
- PXBRQCKWGAHEHS-UHFFFAOYSA-N dichlorodifluoromethane Chemical compound FC(F)(Cl)Cl PXBRQCKWGAHEHS-UHFFFAOYSA-N 0.000 description 3
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- OESNNVJJLZXANA-UHFFFAOYSA-N n-hexyl-2-methyl-n-(3-methyl-1,2,4-oxadiazol-5-yl)propanamide Chemical compound CCCCCCN(C(=O)C(C)C)C1=NC(C)=NO1 OESNNVJJLZXANA-UHFFFAOYSA-N 0.000 description 1
- MMXIZTZWCWYUIF-UHFFFAOYSA-N n-hexyl-3-methyl-1,2,4-oxadiazol-5-amine Chemical compound CCCCCCNC1=NC(C)=NO1 MMXIZTZWCWYUIF-UHFFFAOYSA-N 0.000 description 1
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- DNRPANYGQOCDEW-UHFFFAOYSA-N n-methyl-n-(5-methyl-1,3,4-thiadiazol-2-yl)benzamide Chemical compound N=1N=C(C)SC=1N(C)C(=O)C1=CC=CC=C1 DNRPANYGQOCDEW-UHFFFAOYSA-N 0.000 description 1
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- 239000012044 organic layer Substances 0.000 description 1
- WCPAKWJPBJAGKN-UHFFFAOYSA-N oxadiazole Chemical compound C1=CON=N1 WCPAKWJPBJAGKN-UHFFFAOYSA-N 0.000 description 1
- AICOOMRHRUFYCM-ZRRPKQBOSA-N oxazine, 1 Chemical compound C([C@@H]1[C@H](C(C[C@]2(C)[C@@H]([C@H](C)N(C)C)[C@H](O)C[C@]21C)=O)CC1=CC2)C[C@H]1[C@@]1(C)[C@H]2N=C(C(C)C)OC1 AICOOMRHRUFYCM-ZRRPKQBOSA-N 0.000 description 1
- 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 1
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- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 229920006316 polyvinylpyrrolidine Polymers 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
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- QELSKZZBTMNZEB-UHFFFAOYSA-N propylparaben Chemical compound CCCOC(=O)C1=CC=C(O)C=C1 QELSKZZBTMNZEB-UHFFFAOYSA-N 0.000 description 1
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- COEZWFYORILMOM-UHFFFAOYSA-M sodium 4-[(2,4-dihydroxyphenyl)diazenyl]benzenesulfonate Chemical compound [Na+].OC1=CC(O)=CC=C1N=NC1=CC=C(S([O-])(=O)=O)C=C1 COEZWFYORILMOM-UHFFFAOYSA-M 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 229940080313 sodium starch Drugs 0.000 description 1
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- 235000011152 sodium sulphate Nutrition 0.000 description 1
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- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 235000012222 talc Nutrition 0.000 description 1
- OULAJFUGPPVRBK-UHFFFAOYSA-N tetratriacontyl alcohol Natural products CCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCO OULAJFUGPPVRBK-UHFFFAOYSA-N 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 229940100611 topical cream Drugs 0.000 description 1
- QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 1
- YNJBWRMUSHSURL-UHFFFAOYSA-N trichloroacetic acid Chemical compound OC(=O)C(Cl)(Cl)Cl YNJBWRMUSHSURL-UHFFFAOYSA-N 0.000 description 1
- 125000006493 trifluoromethyl benzyl group Chemical group 0.000 description 1
- 150000004072 triols Chemical class 0.000 description 1
- JFALSRSLKYAFGM-UHFFFAOYSA-N uranium(0) Chemical compound [U] JFALSRSLKYAFGM-UHFFFAOYSA-N 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D271/00—Heterocyclic compounds containing five-membered rings having two nitrogen atoms and one oxygen atom as the only ring hetero atoms
- C07D271/02—Heterocyclic compounds containing five-membered rings having two nitrogen atoms and one oxygen atom as the only ring hetero atoms not condensed with other rings
- C07D271/06—1,2,4-Oxadiazoles; Hydrogenated 1,2,4-oxadiazoles
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D271/00—Heterocyclic compounds containing five-membered rings having two nitrogen atoms and one oxygen atom as the only ring hetero atoms
- C07D271/02—Heterocyclic compounds containing five-membered rings having two nitrogen atoms and one oxygen atom as the only ring hetero atoms not condensed with other rings
- C07D271/06—1,2,4-Oxadiazoles; Hydrogenated 1,2,4-oxadiazoles
- C07D271/07—1,2,4-Oxadiazoles; Hydrogenated 1,2,4-oxadiazoles with oxygen, sulfur or nitrogen atoms, directly attached to ring carbon atoms, the nitrogen atoms not forming part of a nitro radical
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D271/00—Heterocyclic compounds containing five-membered rings having two nitrogen atoms and one oxygen atom as the only ring hetero atoms
- C07D271/02—Heterocyclic compounds containing five-membered rings having two nitrogen atoms and one oxygen atom as the only ring hetero atoms not condensed with other rings
- C07D271/10—1,3,4-Oxadiazoles; Hydrogenated 1,3,4-oxadiazoles
- C07D271/113—1,3,4-Oxadiazoles; Hydrogenated 1,3,4-oxadiazoles with oxygen, sulfur or nitrogen atoms, directly attached to ring carbon atoms, the nitrogen atoms not forming part of a nitro radical
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D285/00—Heterocyclic compounds containing rings having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by groups C07D275/00 - C07D283/00
- C07D285/01—Five-membered rings
- C07D285/02—Thiadiazoles; Hydrogenated thiadiazoles
- C07D285/04—Thiadiazoles; Hydrogenated thiadiazoles not condensed with other rings
- C07D285/08—1,2,4-Thiadiazoles; Hydrogenated 1,2,4-thiadiazoles
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D285/00—Heterocyclic compounds containing rings having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by groups C07D275/00 - C07D283/00
- C07D285/01—Five-membered rings
- C07D285/02—Thiadiazoles; Hydrogenated thiadiazoles
- C07D285/04—Thiadiazoles; Hydrogenated thiadiazoles not condensed with other rings
- C07D285/12—1,3,4-Thiadiazoles; Hydrogenated 1,3,4-thiadiazoles
- C07D285/125—1,3,4-Thiadiazoles; Hydrogenated 1,3,4-thiadiazoles with oxygen, sulfur or nitrogen atoms, directly attached to ring carbon atoms, the nitrogen atoms not forming part of a nitro radical
- C07D285/135—Nitrogen atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Nitrogen- Or Sulfur-Containing Heterocyclic Ring Compounds With Rings Of Six Or More Members (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB24224/75A GB1551735A (en) | 1975-06-05 | 1975-06-05 | Acylated aminothiazoles and aminooxadiazoles |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CS200494B2 true CS200494B2 (en) | 1980-09-15 |
Family
ID=10208350
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CS763692A CS200494B2 (en) | 1975-06-05 | 1976-06-03 | Process for preparing therapeutical acylaminosubstituted five-memberd heterocyclic compounds |
Country Status (34)
Families Citing this family (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2834945A1 (de) * | 1977-08-15 | 1979-03-01 | Lilly Co Eli | Thiadiazolylbenzamide, verfahren zu ihrer herstellung und sie enthaltende insektizide mittel |
| DE2805756A1 (de) * | 1978-02-10 | 1979-08-16 | Bayer Ag | N-azolylalkyl-aniline sowie verfahren zu ihrer herstellung |
| DE2805757A1 (de) * | 1978-02-10 | 1979-08-16 | Bayer Ag | N-azolylalkyl-halogenacetanilide, verfahren zu ihrer herstellung sowie ihre verwendung als herbizide |
| US4285959A (en) * | 1979-05-18 | 1981-08-25 | Ciba-Geigy Corporation | 3-(N-1,3,4-Thiadiazolyl-2)-aminoalkyl-alkyl-acrylates and use thereof as bactericides |
| US4264616A (en) * | 1980-08-29 | 1981-04-28 | Gulf Oil Corporation | 2-Iodoacetylimino-3-methyl-5-trifluoromethyl-1,3,4-thiadiazol-4-ine and use as a fungicide |
| MA19269A1 (fr) * | 1980-09-16 | 1982-04-01 | Lilly Co Eli | Perfectionnement relatif a des derives de n-arylbenzamides . |
| DE3120804A1 (de) | 1981-05-25 | 1982-12-16 | Basf Ag, 6700 Ludwigshafen | N-substituierte 2-methylnaphthylamide, verfahren zu ihrer herstellung und ihre verwendung zur bekaempfung von pilzen |
| US4874864A (en) * | 1988-05-24 | 1989-10-17 | Pfizer Inc. | Benzamide protease inhibitors |
| AU2010601A (en) * | 1999-12-16 | 2001-07-03 | Novartis Ag | Organic compounds |
| TW200503994A (en) * | 2003-01-24 | 2005-02-01 | Novartis Ag | Organic compounds |
| RU2448961C1 (ru) * | 2011-02-03 | 2012-04-27 | Открытое акционерное общество "Всероссийский научный центр по безопасности биологически активных веществ" (ОАО "ВНЦ БАВ") | Фармацевтическая композиция, обладающая противовоспалительной, бронхолитической, противотуберкулезной активностями |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3720684A (en) * | 1970-10-13 | 1973-03-13 | Velsicol Chemical Corp | 5-halo-1,2,4-thiadiazoles |
| IL35743A (en) * | 1970-11-27 | 1974-10-22 | Peretz B | 3-isopropyl-5-amino-1,2,4-thiadiazole compounds |
-
1975
- 1975-06-05 GB GB24224/75A patent/GB1551735A/en not_active Expired
-
1976
- 1976-05-31 NZ NZ181011A patent/NZ181011A/xx unknown
- 1976-05-31 IE IE1148/76A patent/IE43474B1/en unknown
- 1976-05-31 FR FR7616338A patent/FR2313049A1/fr active Granted
- 1976-05-31 IL IL49692A patent/IL49692A/xx unknown
- 1976-05-31 CA CA253,755A patent/CA1085860A/en not_active Expired
- 1976-06-01 GR GR50868A patent/GR60380B/el unknown
- 1976-06-01 AR AR263474A patent/AR217240A1/es active
- 1976-06-01 CH CH685576A patent/CH612427A5/xx not_active IP Right Cessation
- 1976-06-01 ZA ZA00763209A patent/ZA763209B/xx unknown
- 1976-06-02 DK DK243276A patent/DK243276A/da not_active Application Discontinuation
- 1976-06-02 LU LU75070A patent/LU75070A1/xx unknown
- 1976-06-02 SE SE7606226A patent/SE428561B/xx unknown
- 1976-06-03 PT PT65182A patent/PT65182B/pt unknown
- 1976-06-03 YU YU01371/76A patent/YU137176A/xx unknown
- 1976-06-03 CS CS763692A patent/CS200494B2/cs unknown
- 1976-06-03 BE BE6045539A patent/BE842579A/xx not_active IP Right Cessation
- 1976-06-03 HU HU76LI293A patent/HU174191B/hu unknown
- 1976-06-03 AU AU14619/76A patent/AU503150B2/en not_active Expired
- 1976-06-04 FI FI761585A patent/FI63394C/fi not_active IP Right Cessation
- 1976-06-04 ES ES448590A patent/ES448590A1/es not_active Expired
- 1976-06-04 JP JP51066027A patent/JPS51146468A/ja active Pending
- 1976-06-04 PH PH18535A patent/PH16077A/en unknown
- 1976-06-04 DD DD193198A patent/DD125075A5/xx unknown
- 1976-06-04 SU SU762366751A patent/SU639451A3/ru active
- 1976-06-04 MX MX000265U patent/MX3483E/es unknown
- 1976-06-04 PL PL1976190132A patent/PL103004B1/pl unknown
- 1976-06-04 BG BG033366A patent/BG27359A3/xx unknown
- 1976-06-04 AT AT412276A patent/AT346843B/de not_active IP Right Cessation
- 1976-06-04 DE DE19762625285 patent/DE2625285A1/de not_active Ceased
- 1976-06-04 NO NO761913A patent/NO144346C/no unknown
- 1976-06-05 EG EG76334A patent/EG12226A/xx active
- 1976-06-05 OA OA55843A patent/OA05346A/xx unknown
- 1976-06-08 NL NL7606178A patent/NL7606178A/xx not_active Application Discontinuation
-
1979
- 1979-01-10 CH CH20579A patent/CH616933A5/fr not_active IP Right Cessation
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