DE2146395C3 - N-p-Toluolsulfonyl-5-methyl- d2 -pyrazolin-1karbonamid und Verfahren zu seiner Herstellung - Google Patents
N-p-Toluolsulfonyl-5-methyl- d2 -pyrazolin-1karbonamid und Verfahren zu seiner HerstellungInfo
- Publication number
- DE2146395C3 DE2146395C3 DE2146395A DE2146395A DE2146395C3 DE 2146395 C3 DE2146395 C3 DE 2146395C3 DE 2146395 A DE2146395 A DE 2146395A DE 2146395 A DE2146395 A DE 2146395A DE 2146395 C3 DE2146395 C3 DE 2146395C3
- Authority
- DE
- Germany
- Prior art keywords
- preparation
- temperature
- methyl
- pyrazoline
- spc
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- 238000002360 preparation method Methods 0.000 title description 25
- 238000000034 method Methods 0.000 title description 9
- 150000001875 compounds Chemical class 0.000 claims description 13
- OUUYOZGHNAGYNC-UHFFFAOYSA-N 3-methyl-n-(4-methylphenyl)sulfonyl-3,4-dihydropyrazole-2-carboxamide Chemical compound CC1CC=NN1C(=O)NS(=O)(=O)C1=CC=C(C)C=C1 OUUYOZGHNAGYNC-UHFFFAOYSA-N 0.000 description 14
- 239000000243 solution Substances 0.000 description 13
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 10
- JLRGJRBPOGGCBT-UHFFFAOYSA-N Tolbutamide Chemical compound CCCCNC(=O)NS(=O)(=O)C1=CC=C(C)C=C1 JLRGJRBPOGGCBT-UHFFFAOYSA-N 0.000 description 10
- 239000002904 solvent Substances 0.000 description 10
- 229960005371 tolbutamide Drugs 0.000 description 10
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
- 239000000203 mixture Substances 0.000 description 9
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 8
- 241000700159 Rattus Species 0.000 description 7
- 238000009835 boiling Methods 0.000 description 7
- 230000000694 effects Effects 0.000 description 7
- MCGBIXXDQFWVDW-UHFFFAOYSA-N 4,5-dihydro-1h-pyrazole Chemical compound C1CC=NN1 MCGBIXXDQFWVDW-UHFFFAOYSA-N 0.000 description 6
- 241000699670 Mus sp. Species 0.000 description 6
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 5
- 210000004369 blood Anatomy 0.000 description 5
- 239000008280 blood Substances 0.000 description 5
- 238000002844 melting Methods 0.000 description 5
- 230000008018 melting Effects 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- 230000037396 body weight Effects 0.000 description 4
- 239000007795 chemical reaction product Substances 0.000 description 4
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 3
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 3
- RKWGIWYCVPQPMF-UHFFFAOYSA-N Chloropropamide Chemical compound CCCNC(=O)NS(=O)(=O)C1=CC=C(Cl)C=C1 RKWGIWYCVPQPMF-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 235000011114 ammonium hydroxide Nutrition 0.000 description 3
- 229960001761 chlorpropamide Drugs 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- 241001465754 Metazoa Species 0.000 description 2
- 241000283973 Oryctolagus cuniculus Species 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 230000008030 elimination Effects 0.000 description 2
- 238000003379 elimination reaction Methods 0.000 description 2
- 239000000284 extract Substances 0.000 description 2
- 238000000605 extraction Methods 0.000 description 2
- 230000002218 hypoglycaemic effect Effects 0.000 description 2
- 239000012442 inert solvent Substances 0.000 description 2
- 210000003734 kidney Anatomy 0.000 description 2
- 210000004185 liver Anatomy 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 230000020477 pH reduction Effects 0.000 description 2
- 210000000496 pancreas Anatomy 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 210000000952 spleen Anatomy 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- 238000005979 thermal decomposition reaction Methods 0.000 description 2
- 231100000419 toxicity Toxicity 0.000 description 2
- 230000001988 toxicity Effects 0.000 description 2
- RUTYWCZSEBLPAK-UHFFFAOYSA-N (4-methylphenyl)sulfonylurea Chemical compound CC1=CC=C(S(=O)(=O)NC(N)=O)C=C1 RUTYWCZSEBLPAK-UHFFFAOYSA-N 0.000 description 1
- 102000013142 Amylases Human genes 0.000 description 1
- 108010065511 Amylases Proteins 0.000 description 1
- 102000001554 Hemoglobins Human genes 0.000 description 1
- 108010054147 Hemoglobins Proteins 0.000 description 1
- 208000013016 Hypoglycemia Diseases 0.000 description 1
- 241000699666 Mus <mouse, genus> Species 0.000 description 1
- 206010028980 Neoplasm Diseases 0.000 description 1
- 102000003929 Transaminases Human genes 0.000 description 1
- 108090000340 Transaminases Proteins 0.000 description 1
- 238000009825 accumulation Methods 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 238000004820 blood count Methods 0.000 description 1
- 230000036765 blood level Effects 0.000 description 1
- 238000009534 blood test Methods 0.000 description 1
- 210000004556 brain Anatomy 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 201000011510 cancer Diseases 0.000 description 1
- 125000005521 carbonamide group Chemical group 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 231100000160 chronic toxicity Toxicity 0.000 description 1
- 230000007665 chronic toxicity Effects 0.000 description 1
- 231100000132 chronic toxicity testing Toxicity 0.000 description 1
- 229940111205 diastase Drugs 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 210000003743 erythrocyte Anatomy 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- 230000002496 gastric effect Effects 0.000 description 1
- 230000004110 gluconeogenesis Effects 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- 230000003914 insulin secretion Effects 0.000 description 1
- 210000000936 intestine Anatomy 0.000 description 1
- 210000000265 leukocyte Anatomy 0.000 description 1
- 231100001252 long-term toxicity Toxicity 0.000 description 1
- 230000007774 longterm Effects 0.000 description 1
- 210000004072 lung Anatomy 0.000 description 1
- 230000036210 malignancy Effects 0.000 description 1
- 230000010534 mechanism of action Effects 0.000 description 1
- 210000004165 myocardium Anatomy 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 210000000056 organ Anatomy 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 210000002027 skeletal muscle Anatomy 0.000 description 1
- 230000004936 stimulating effect Effects 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 231100000816 toxic dose Toxicity 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/06—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Photoreceptors In Electrophotography (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP11039572A JPS4897500A (cg-RX-API-DMAC10.html) | 1971-09-16 | 1972-11-06 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| PL14331970A PL76607B1 (cg-RX-API-DMAC10.html) | 1970-09-19 | 1970-09-19 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DE2146395A1 DE2146395A1 (de) | 1972-04-13 |
| DE2146395B2 DE2146395B2 (de) | 1980-01-31 |
| DE2146395C3 true DE2146395C3 (de) | 1980-10-09 |
Family
ID=19952384
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2146395A Expired DE2146395C3 (de) | 1970-09-19 | 1971-09-16 | N-p-Toluolsulfonyl-5-methyl- d2 -pyrazolin-1karbonamid und Verfahren zu seiner Herstellung |
Country Status (10)
| Country | Link |
|---|---|
| US (1) | US3780058A (cg-RX-API-DMAC10.html) |
| JP (1) | JPS5038107B1 (cg-RX-API-DMAC10.html) |
| DE (1) | DE2146395C3 (cg-RX-API-DMAC10.html) |
| DK (1) | DK133467B (cg-RX-API-DMAC10.html) |
| FR (1) | FR2106632B1 (cg-RX-API-DMAC10.html) |
| GB (1) | GB1326835A (cg-RX-API-DMAC10.html) |
| HU (1) | HU162318B (cg-RX-API-DMAC10.html) |
| NL (1) | NL162905C (cg-RX-API-DMAC10.html) |
| PL (1) | PL76607B1 (cg-RX-API-DMAC10.html) |
| SU (2) | SU466659A3 (cg-RX-API-DMAC10.html) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3781769T2 (de) * | 1986-10-31 | 1993-02-11 | Duphar Int Res | 1-carbamoyl-2-pyrazolin-derivate mit herbizidischer wirkung. |
| US8410135B2 (en) * | 2007-06-15 | 2013-04-02 | Solvay Pharmaceuticals B.V. | 4,5 dihydro-(1H)-pyrazole derivatives as cannabinoid CB1 receptor modulators |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NL282558A (cg-RX-API-DMAC10.html) * |
-
1970
- 1970-09-19 PL PL14331970A patent/PL76607B1/xx unknown
-
1971
- 1971-09-02 GB GB4089071A patent/GB1326835A/en not_active Expired
- 1971-09-07 DK DK438871AA patent/DK133467B/da unknown
- 1971-09-16 US US00181009A patent/US3780058A/en not_active Expired - Lifetime
- 1971-09-16 JP JP46072138A patent/JPS5038107B1/ja active Pending
- 1971-09-16 DE DE2146395A patent/DE2146395C3/de not_active Expired
- 1971-09-17 SU SU1941907A patent/SU466659A3/ru active
- 1971-09-17 NL NL7112819.A patent/NL162905C/xx not_active IP Right Cessation
- 1971-09-17 SU SU1698633A patent/SU439977A3/ru active
- 1971-09-18 HU HUSA2245A patent/HU162318B/hu unknown
- 1971-09-20 FR FR7133730A patent/FR2106632B1/fr not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| NL162905C (nl) | 1980-07-15 |
| US3780058A (en) | 1973-12-18 |
| DK133467B (da) | 1976-05-24 |
| NL7112819A (cg-RX-API-DMAC10.html) | 1972-03-21 |
| JPS5038107B1 (cg-RX-API-DMAC10.html) | 1975-12-06 |
| DK133467C (cg-RX-API-DMAC10.html) | 1976-10-18 |
| SU466659A3 (ru) | 1975-04-05 |
| NL162905B (nl) | 1980-02-15 |
| FR2106632B1 (cg-RX-API-DMAC10.html) | 1975-04-18 |
| GB1326835A (en) | 1973-08-15 |
| DE2146395A1 (de) | 1972-04-13 |
| DE2146395B2 (de) | 1980-01-31 |
| HU162318B (cg-RX-API-DMAC10.html) | 1973-01-29 |
| PL76607B1 (cg-RX-API-DMAC10.html) | 1975-02-28 |
| FR2106632A1 (cg-RX-API-DMAC10.html) | 1972-05-05 |
| SU439977A3 (ru) | 1974-08-15 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C3 | Grant after two publication steps (3rd publication) | ||
| 8339 | Ceased/non-payment of the annual fee |