CH626079A5 - Process for the preparation of 2-cyclopropanecarboxamido-5-halothiazole - Google Patents
Process for the preparation of 2-cyclopropanecarboxamido-5-halothiazole Download PDFInfo
- Publication number
- CH626079A5 CH626079A5 CH231777A CH231777A CH626079A5 CH 626079 A5 CH626079 A5 CH 626079A5 CH 231777 A CH231777 A CH 231777A CH 231777 A CH231777 A CH 231777A CH 626079 A5 CH626079 A5 CH 626079A5
- Authority
- CH
- Switzerland
- Prior art keywords
- formula
- compound
- edema
- halothiazole
- compounds
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 10
- 238000002360 preparation method Methods 0.000 title claims description 8
- 150000001875 compounds Chemical class 0.000 claims description 26
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 3
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 3
- 229910052794 bromium Inorganic materials 0.000 claims description 3
- 229910052801 chlorine Inorganic materials 0.000 claims description 3
- 239000000460 chlorine Substances 0.000 claims description 3
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 3
- ZOOSILUVXHVRJE-UHFFFAOYSA-N cyclopropanecarbonyl chloride Chemical compound ClC(=O)C1CC1 ZOOSILUVXHVRJE-UHFFFAOYSA-N 0.000 claims description 3
- 229910052731 fluorine Chemical group 0.000 claims description 3
- 239000011737 fluorine Chemical group 0.000 claims description 3
- 229910052740 iodine Inorganic materials 0.000 claims description 3
- 239000011630 iodine Chemical group 0.000 claims description 3
- NUSVDASTCPBUIP-UHFFFAOYSA-N (5-bromo-1,3-thiazol-2-yl)azanium;bromide Chemical compound [Br-].BrC1=C[NH2+]C(=N)S1 NUSVDASTCPBUIP-UHFFFAOYSA-N 0.000 claims description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical group FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 2
- 125000001246 bromo group Chemical group Br* 0.000 claims 1
- 125000001153 fluoro group Chemical group F* 0.000 claims 1
- MXJKAJTZKDDREU-UHFFFAOYSA-N n-(5-bromo-1,3-thiazol-2-yl)cyclopropanecarboxamide Chemical compound S1C(Br)=CN=C1NC(=O)C1CC1 MXJKAJTZKDDREU-UHFFFAOYSA-N 0.000 claims 1
- 206010030113 Oedema Diseases 0.000 description 15
- 241000700159 Rattus Species 0.000 description 9
- 235000010418 carrageenan Nutrition 0.000 description 5
- 229920001525 carrageenan Polymers 0.000 description 5
- 239000000725 suspension Substances 0.000 description 5
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 4
- 230000005764 inhibitory process Effects 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- 230000003110 anti-inflammatory effect Effects 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- 238000002474 experimental method Methods 0.000 description 3
- 210000000548 hind-foot Anatomy 0.000 description 3
- 239000002674 ointment Substances 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
- 229940121363 anti-inflammatory agent Drugs 0.000 description 2
- 239000002260 anti-inflammatory agent Substances 0.000 description 2
- 239000002775 capsule Substances 0.000 description 2
- 210000002683 foot Anatomy 0.000 description 2
- 238000002347 injection Methods 0.000 description 2
- 239000007924 injection Substances 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 229920000609 methyl cellulose Polymers 0.000 description 2
- 239000001923 methylcellulose Substances 0.000 description 2
- 235000010981 methylcellulose Nutrition 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 235000019271 petrolatum Nutrition 0.000 description 2
- 229960002895 phenylbutazone Drugs 0.000 description 2
- VYMDGNCVAMGZFE-UHFFFAOYSA-N phenylbutazonum Chemical compound O=C1C(CCCC)C(=O)N(C=2C=CC=CC=2)N1C1=CC=CC=C1 VYMDGNCVAMGZFE-UHFFFAOYSA-N 0.000 description 2
- 239000006187 pill Substances 0.000 description 2
- 239000000829 suppository Substances 0.000 description 2
- 239000003826 tablet Substances 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000000679 carrageenan Substances 0.000 description 1
- 229940113118 carrageenan Drugs 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000006071 cream Substances 0.000 description 1
- 238000006073 displacement reaction Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- 230000004054 inflammatory process Effects 0.000 description 1
- 229940102223 injectable solution Drugs 0.000 description 1
- 229940102213 injectable suspension Drugs 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- 239000006210 lotion Substances 0.000 description 1
- 238000000691 measurement method Methods 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 239000003182 parenteral nutrition solution Substances 0.000 description 1
- 230000004526 pharmaceutical effect Effects 0.000 description 1
- 239000000825 pharmaceutical preparation Substances 0.000 description 1
- 230000035479 physiological effects, processes and functions Effects 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- 239000012258 stirred mixture Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
- UHVMMEOXYDMDKI-JKYCWFKZSA-L zinc;1-(5-cyanopyridin-2-yl)-3-[(1s,2s)-2-(6-fluoro-2-hydroxy-3-propanoylphenyl)cyclopropyl]urea;diacetate Chemical compound [Zn+2].CC([O-])=O.CC([O-])=O.CCC(=O)C1=CC=C(F)C([C@H]2[C@H](C2)NC(=O)NC=2N=CC(=CC=2)C#N)=C1O UHVMMEOXYDMDKI-JKYCWFKZSA-L 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
- C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D277/32—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members 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 to ring carbon atoms
- C07D277/38—Nitrogen atoms
- C07D277/44—Acylated amino or imino radicals
- C07D277/46—Acylated amino or imino radicals by carboxylic acids, or sulfur or nitrogen analogues thereof
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Pain & Pain Management (AREA)
- Rheumatology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (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)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US05/676,770 US4027031A (en) | 1975-04-28 | 1976-04-14 | 2-Cyclopropanecarboxamido-S-halothiazole as anti-inflammatory agents |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH626079A5 true CH626079A5 (en) | 1981-10-30 |
Family
ID=24715924
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH231777A CH626079A5 (en) | 1976-04-14 | 1977-02-24 | Process for the preparation of 2-cyclopropanecarboxamido-5-halothiazole |
Country Status (13)
| Country | Link |
|---|---|
| JP (1) | JPS52125164A (OSRAM) |
| AT (1) | AT350316B (OSRAM) |
| AU (1) | AU2220177A (OSRAM) |
| BE (1) | BE852075A (OSRAM) |
| CA (1) | CA1068607A (OSRAM) |
| CH (1) | CH626079A5 (OSRAM) |
| DE (1) | DE2708327A1 (OSRAM) |
| FR (1) | FR2348206A1 (OSRAM) |
| GR (1) | GR66154B (OSRAM) |
| IL (1) | IL51483A0 (OSRAM) |
| NL (1) | NL7702432A (OSRAM) |
| PH (1) | PH11483A (OSRAM) |
| PT (1) | PT66258B (OSRAM) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS57136579A (en) * | 1981-01-21 | 1982-08-23 | Mitsui Toatsu Chem Inc | Thiazolylurea derivative, its preparation, and pharmaceutical composition containing the same |
| DE3264595D1 (en) * | 1981-01-08 | 1985-08-14 | Mitsui Toatsu Chemicals | N-(4-phenyl-2-thiazolyl)carbamate derivatives, process for their preparation, and medicinal composition containing same |
| JPS57116067A (en) * | 1981-01-12 | 1982-07-19 | Sankyo Kagaku Kk | Novel 8-quinolinesulfonyl derivative, its synthesis and use |
| WO1982002386A1 (en) * | 1981-01-13 | 1982-07-22 | Sakano Isao | Aminothiazole derivatives,process for their preparation,and medicinal composition containing same |
| US4501750A (en) * | 1981-01-13 | 1985-02-26 | Mitsui Toatsu Kaguku Kabushiki Kaisha | Thiazole compounds, a process for preparing same and a pharmaceutical composition containing the thiazole compounds |
| GB9823871D0 (en) * | 1998-10-30 | 1998-12-23 | Pharmacia & Upjohn Spa | 2-Amino-thiazole derivatives, process for their preparation, and their use as antitumour agents |
-
1977
- 1977-02-01 CA CA270,844A patent/CA1068607A/en not_active Expired
- 1977-02-11 AU AU22201/77A patent/AU2220177A/en not_active Expired
- 1977-02-14 AT AT98477A patent/AT350316B/de not_active IP Right Cessation
- 1977-02-16 FR FR7704350A patent/FR2348206A1/fr active Granted
- 1977-02-17 IL IL51483A patent/IL51483A0/xx unknown
- 1977-02-18 JP JP1704977A patent/JPS52125164A/ja active Pending
- 1977-02-24 PH PH19491A patent/PH11483A/en unknown
- 1977-02-24 CH CH231777A patent/CH626079A5/de not_active IP Right Cessation
- 1977-02-25 DE DE19772708327 patent/DE2708327A1/de not_active Withdrawn
- 1977-02-25 GR GR52850A patent/GR66154B/el unknown
- 1977-03-02 PT PT66258A patent/PT66258B/pt unknown
- 1977-03-04 BE BE2055711A patent/BE852075A/xx not_active IP Right Cessation
- 1977-03-07 NL NL7702432A patent/NL7702432A/xx not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| NL7702432A (nl) | 1977-10-18 |
| ATA98477A (de) | 1978-10-15 |
| GR66154B (OSRAM) | 1981-01-19 |
| DE2708327A1 (de) | 1977-11-03 |
| CA1068607A (en) | 1979-12-25 |
| AU2220177A (en) | 1978-08-17 |
| FR2348206A1 (fr) | 1977-11-10 |
| FR2348206B1 (OSRAM) | 1980-03-07 |
| PH11483A (en) | 1978-02-01 |
| AT350316B (de) | 1979-05-25 |
| IL51483A0 (en) | 1977-04-29 |
| PT66258B (en) | 1978-08-07 |
| BE852075A (nl) | 1977-09-05 |
| PT66258A (en) | 1977-04-01 |
| JPS52125164A (en) | 1977-10-20 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PL | Patent ceased | ||
| PL | Patent ceased |