CZ282024B6 - Amidy kyseliny alfa-aryl-alfa-hydroxy-beta-imida zolinyl-propionové - Google Patents
Amidy kyseliny alfa-aryl-alfa-hydroxy-beta-imida zolinyl-propionové Download PDFInfo
- Publication number
- CZ282024B6 CZ282024B6 CS923722A CS372292A CZ282024B6 CZ 282024 B6 CZ282024 B6 CZ 282024B6 CS 923722 A CS923722 A CS 923722A CS 372292 A CS372292 A CS 372292A CZ 282024 B6 CZ282024 B6 CZ 282024B6
- Authority
- CZ
- Czechia
- Prior art keywords
- group
- carbon atoms
- alkyl
- fluorine
- chlorine
- Prior art date
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- 238000000034 method Methods 0.000 title claims abstract description 18
- 238000002360 preparation method Methods 0.000 title claims abstract description 11
- XBDQKXXYIPTUBI-UHFFFAOYSA-N Propionic acid Substances CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 title claims description 4
- 239000008194 pharmaceutical composition Substances 0.000 title claims description 3
- 239000003814 drug Substances 0.000 claims abstract description 4
- 239000000460 chlorine Chemical group 0.000 claims description 32
- 125000004432 carbon atom Chemical group C* 0.000 claims description 27
- 125000000217 alkyl group Chemical group 0.000 claims description 18
- 229910052801 chlorine Inorganic materials 0.000 claims description 16
- 229910052731 fluorine Inorganic materials 0.000 claims description 15
- 239000011737 fluorine Substances 0.000 claims description 15
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 10
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 10
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 10
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- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 6
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- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 6
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- 125000001424 substituent group Chemical group 0.000 claims description 5
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- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 4
- 229910052794 bromium Inorganic materials 0.000 claims description 4
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- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 1
- FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 1
- RGSFGYAAUTVSQA-UHFFFAOYSA-N pentamethylene Natural products C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 description 1
- 125000004817 pentamethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 239000006187 pill Substances 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- FVSKHRXBFJPNKK-UHFFFAOYSA-N propionitrile Chemical compound CCC#N FVSKHRXBFJPNKK-UHFFFAOYSA-N 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 229960004889 salicylic acid Drugs 0.000 description 1
- 239000000523 sample Substances 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 239000002904 solvent Substances 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
- 241000894007 species Species 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 238000010186 staining Methods 0.000 description 1
- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 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
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/04—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D233/20—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with substituted hydrocarbon radicals, directly attached to ring carbon atoms
- C07D233/26—Radicals substituted by carbon atoms having three bonds to hetero atoms
-
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/04—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D233/06—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to ring carbon atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Diabetes (AREA)
- Medicinal Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Hematology (AREA)
- Obesity (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Emergency Medicine (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Endocrinology (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Plural Heterocyclic Compounds (AREA)
- Peptides Or Proteins (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE4201709A DE4201709A1 (de) | 1992-01-23 | 1992-01-23 | (alpha)-aryl-(alpha)-hydroxy-ss-imidazolinyl-propionsaeureamide |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CZ372292A3 CZ372292A3 (en) | 1993-12-15 |
| CZ282024B6 true CZ282024B6 (cs) | 1997-04-16 |
Family
ID=6450062
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CS923722A CZ282024B6 (cs) | 1992-01-23 | 1992-12-17 | Amidy kyseliny alfa-aryl-alfa-hydroxy-beta-imida zolinyl-propionové |
Country Status (22)
| Country | Link |
|---|---|
| US (1) | US5334610A (en, 2012) |
| EP (1) | EP0552631B1 (en, 2012) |
| JP (1) | JPH05286942A (en, 2012) |
| KR (1) | KR930016401A (en, 2012) |
| CN (1) | CN1075714A (en, 2012) |
| AT (1) | ATE158576T1 (en, 2012) |
| AU (1) | AU650807B2 (en, 2012) |
| CA (1) | CA2087650A1 (en, 2012) |
| CZ (1) | CZ282024B6 (en, 2012) |
| DE (2) | DE4201709A1 (en, 2012) |
| DK (1) | DK0552631T3 (en, 2012) |
| ES (1) | ES2107562T3 (en, 2012) |
| GR (1) | GR3025179T3 (en, 2012) |
| HU (1) | HUT63394A (en, 2012) |
| IL (1) | IL104444A (en, 2012) |
| MX (1) | MX9300136A (en, 2012) |
| MY (1) | MY108826A (en, 2012) |
| NZ (1) | NZ245726A (en, 2012) |
| PL (1) | PL172005B1 (en, 2012) |
| SK (1) | SK278548B6 (en, 2012) |
| TW (1) | TW232011B (en, 2012) |
| ZA (1) | ZA93477B (en, 2012) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6403818B1 (en) | 2000-02-28 | 2002-06-11 | Eisai Co., Ltd. | Process for producing α-hydroxy-carbonyl compound |
| US7439383B2 (en) | 2002-04-18 | 2008-10-21 | University Of Virginia Patent Foundation | Sodium channel blockers |
| WO2004050039A2 (en) * | 2002-12-04 | 2004-06-17 | Merck & Co., Inc. | Spirocyclic ureas, compositions containing such compounds and methods of use |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| SE7605958L (sv) * | 1975-05-30 | 1976-12-01 | Scherico Ltd | Nya 2-imidazoliner och deras anvendning sasom hypoglykemiska medel |
| DE2614240C3 (de) * | 1976-04-02 | 1980-03-06 | Bayer Ag, 5090 Leverkusen | Verfahren zur Herstellung von Acylcyaniden |
| JPS5936885B2 (ja) * | 1976-06-24 | 1984-09-06 | 第一製薬株式会社 | 糖尿病治療剤 |
| US4136188A (en) * | 1976-06-25 | 1979-01-23 | Daiichi Seiyaku Co., Ltd. | Treatment of diabetes with 2-substituted-1,3-diazacyclic compounds |
| US4226876A (en) * | 1976-12-20 | 1980-10-07 | Burroughs Wellcome Co. | Arthropodicidal imidazoline derivatives |
| DK344489D0 (da) * | 1989-07-12 | 1989-07-12 | Novo Nordisk As | Substituerede 2-imidazoliner og fremstilling og anvendelse deraf |
-
1992
- 1992-01-23 DE DE4201709A patent/DE4201709A1/de not_active Withdrawn
- 1992-12-17 CZ CS923722A patent/CZ282024B6/cs unknown
- 1992-12-17 SK SK3722-92A patent/SK278548B6/sk unknown
- 1992-12-28 TW TW081110391A patent/TW232011B/zh active
-
1993
- 1993-01-06 MY MYPI93000017A patent/MY108826A/en unknown
- 1993-01-11 DE DE59307401T patent/DE59307401D1/de not_active Expired - Fee Related
- 1993-01-11 AT AT93100273T patent/ATE158576T1/de not_active IP Right Cessation
- 1993-01-11 DK DK93100273.7T patent/DK0552631T3/da active
- 1993-01-11 EP EP93100273A patent/EP0552631B1/de not_active Expired - Lifetime
- 1993-01-11 ES ES93100273T patent/ES2107562T3/es not_active Expired - Lifetime
- 1993-01-12 MX MX9300136A patent/MX9300136A/es not_active Application Discontinuation
- 1993-01-14 US US08/004,341 patent/US5334610A/en not_active Expired - Fee Related
- 1993-01-19 AU AU31888/93A patent/AU650807B2/en not_active Ceased
- 1993-01-19 JP JP5023222A patent/JPH05286942A/ja active Pending
- 1993-01-20 CA CA002087650A patent/CA2087650A1/en not_active Abandoned
- 1993-01-20 IL IL104444A patent/IL104444A/xx not_active IP Right Cessation
- 1993-01-21 PL PL93297491A patent/PL172005B1/pl unknown
- 1993-01-21 KR KR1019930000821A patent/KR930016401A/ko not_active Ceased
- 1993-01-21 CN CN93101131A patent/CN1075714A/zh active Pending
- 1993-01-21 NZ NZ245726A patent/NZ245726A/en unknown
- 1993-01-22 HU HU9300181A patent/HUT63394A/hu unknown
- 1993-01-22 ZA ZA93477A patent/ZA93477B/xx unknown
-
1997
- 1997-10-29 GR GR970402814T patent/GR3025179T3/el unknown
Also Published As
| Publication number | Publication date |
|---|---|
| SK372292A3 (en) | 1997-09-10 |
| KR930016401A (ko) | 1993-08-26 |
| DE4201709A1 (de) | 1993-07-29 |
| HUT63394A (en) | 1993-08-30 |
| HU9300181D0 (en) | 1993-04-28 |
| GR3025179T3 (en) | 1998-02-27 |
| MY108826A (en) | 1996-11-30 |
| IL104444A (en) | 1997-06-10 |
| MX9300136A (es) | 1993-07-01 |
| US5334610A (en) | 1994-08-02 |
| IL104444A0 (en) | 1993-05-13 |
| SK278548B6 (en) | 1997-09-10 |
| JPH05286942A (ja) | 1993-11-02 |
| CN1075714A (zh) | 1993-09-01 |
| ES2107562T3 (es) | 1997-12-01 |
| PL297491A1 (en) | 1993-08-09 |
| EP0552631B1 (de) | 1997-09-24 |
| PL172005B1 (pl) | 1997-07-31 |
| TW232011B (en, 2012) | 1994-10-11 |
| ZA93477B (en) | 1993-08-23 |
| AU3188893A (en) | 1993-07-29 |
| EP0552631A1 (de) | 1993-07-28 |
| DE59307401D1 (de) | 1997-10-30 |
| ATE158576T1 (de) | 1997-10-15 |
| DK0552631T3 (da) | 1998-05-11 |
| AU650807B2 (en) | 1994-06-30 |
| CA2087650A1 (en) | 1993-07-24 |
| CZ372292A3 (en) | 1993-12-15 |
| NZ245726A (en) | 1996-01-26 |
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