DE3010751A1 - Verwendung von 9-chlor-7-(1h-tetrazol-5-yl)-5-oxo-5h(1h) benzopyrano(2,3-b) pyridin und seinen salzen und hydraten bei der behandlung von rheumatischen beschwerden - Google Patents
Verwendung von 9-chlor-7-(1h-tetrazol-5-yl)-5-oxo-5h(1h) benzopyrano(2,3-b) pyridin und seinen salzen und hydraten bei der behandlung von rheumatischen beschwerdenInfo
- Publication number
- DE3010751A1 DE3010751A1 DE19803010751 DE3010751A DE3010751A1 DE 3010751 A1 DE3010751 A1 DE 3010751A1 DE 19803010751 DE19803010751 DE 19803010751 DE 3010751 A DE3010751 A DE 3010751A DE 3010751 A1 DE3010751 A1 DE 3010751A1
- Authority
- DE
- Germany
- Prior art keywords
- treatment
- tetrazol
- benzopyrano
- pyridine
- salts
- 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.)
- Granted
Links
- 208000025747 Rheumatic disease Diseases 0.000 title claims description 8
- 230000000552 rheumatic effect Effects 0.000 title claims description 8
- 150000004677 hydrates Chemical class 0.000 title claims 3
- -1 1H-tetrazol-5-yl Chemical group 0.000 claims description 6
- 150000003839 salts Chemical class 0.000 claims description 4
- MXIYRNSRKGMBLQ-UHFFFAOYSA-N 5h-chromeno[2,3-b]pyridine Chemical compound C1=CC=C2CC3=CC=CC=C3OC2=N1 MXIYRNSRKGMBLQ-UHFFFAOYSA-N 0.000 claims 2
- BQARKRSSWQHWNE-UHFFFAOYSA-N 9-chloro-7-(2h-tetrazol-5-yl)-1,2-dihydrochromeno[2,3-b]pyridin-5-one Chemical compound C=1C(C(C=2C=CCNC=2O2)=O)=C2C(Cl)=CC=1C1=NN=NN1 BQARKRSSWQHWNE-UHFFFAOYSA-N 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 description 25
- 238000012360 testing method Methods 0.000 description 8
- 230000015572 biosynthetic process Effects 0.000 description 7
- 210000002683 foot Anatomy 0.000 description 7
- 241000699670 Mus sp. Species 0.000 description 6
- 241000700159 Rattus Species 0.000 description 6
- 210000002966 serum Anatomy 0.000 description 6
- 206010003246 arthritis Diseases 0.000 description 5
- 210000000865 mononuclear phagocyte system Anatomy 0.000 description 5
- 206010039073 rheumatoid arthritis Diseases 0.000 description 5
- 241001465754 Metazoa Species 0.000 description 4
- 230000007059 acute toxicity Effects 0.000 description 4
- 231100000403 acute toxicity Toxicity 0.000 description 4
- 235000010418 carrageenan Nutrition 0.000 description 4
- 229920001525 carrageenan Polymers 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 238000002474 experimental method Methods 0.000 description 4
- 230000005764 inhibitory process Effects 0.000 description 4
- 238000002347 injection Methods 0.000 description 4
- 239000007924 injection Substances 0.000 description 4
- 238000007912 intraperitoneal administration Methods 0.000 description 4
- 208000009386 Experimental Arthritis Diseases 0.000 description 3
- 206010070834 Sensitisation Diseases 0.000 description 3
- 239000002671 adjuvant Substances 0.000 description 3
- 230000001684 chronic effect Effects 0.000 description 3
- 230000003247 decreasing effect Effects 0.000 description 3
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- 239000008187 granular material Substances 0.000 description 3
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- 238000000034 method Methods 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 210000001539 phagocyte Anatomy 0.000 description 3
- 230000008313 sensitization Effects 0.000 description 3
- NHBKXEKEPDILRR-UHFFFAOYSA-N 2,3-bis(butanoylsulfanyl)propyl butanoate Chemical compound CCCC(=O)OCC(SC(=O)CCC)CSC(=O)CCC NHBKXEKEPDILRR-UHFFFAOYSA-N 0.000 description 2
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 2
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 2
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 description 2
- 241001494479 Pecora Species 0.000 description 2
- 241000700157 Rattus norvegicus Species 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 210000001744 T-lymphocyte Anatomy 0.000 description 2
- 230000004520 agglutination Effects 0.000 description 2
- 239000000427 antigen Substances 0.000 description 2
- 102000036639 antigens Human genes 0.000 description 2
- 108091007433 antigens Proteins 0.000 description 2
- 210000004369 blood Anatomy 0.000 description 2
- 239000008280 blood Substances 0.000 description 2
- 159000000007 calcium salts Chemical class 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 229940079593 drug Drugs 0.000 description 2
- 210000003743 erythrocyte Anatomy 0.000 description 2
- 239000008101 lactose Substances 0.000 description 2
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 238000002560 therapeutic procedure Methods 0.000 description 2
- XASLRUHPXHMOCS-UHFFFAOYSA-N 2-[2-chloro-4-(2h-tetrazol-5-yl)phenoxy]pyridine-3-carboxylic acid Chemical compound OC(=O)C1=CC=CN=C1OC1=CC=C(C=2NN=NN=2)C=C1Cl XASLRUHPXHMOCS-UHFFFAOYSA-N 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 229920002153 Hydroxypropyl cellulose Polymers 0.000 description 1
- 108060003951 Immunoglobulin Proteins 0.000 description 1
- 206010061218 Inflammation Diseases 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 241000906446 Theraps Species 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 229940124599 anti-inflammatory drug Drugs 0.000 description 1
- 230000003110 anti-inflammatory effect Effects 0.000 description 1
- 230000003356 anti-rheumatic effect Effects 0.000 description 1
- 239000000043 antiallergic agent Substances 0.000 description 1
- 239000003435 antirheumatic agent Substances 0.000 description 1
- 244000052616 bacterial pathogen Species 0.000 description 1
- 230000036772 blood pressure Effects 0.000 description 1
- 230000037396 body weight Effects 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000004359 castor oil Substances 0.000 description 1
- 235000019438 castor oil Nutrition 0.000 description 1
- 239000001913 cellulose Substances 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 239000012050 conventional carrier Substances 0.000 description 1
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical class CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 210000004051 gastric juice Anatomy 0.000 description 1
- ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Natural products CCCCCC[C@@H](O)CC=CCCCCCCCC(=O)OC[C@@H](COC(=O)CCCCCCCC=CC[C@@H](O)CCCCCC)OC(=O)CCCCCCCC=CC[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-XOQCFJPHSA-N 0.000 description 1
- 210000000548 hind-foot Anatomy 0.000 description 1
- 239000001863 hydroxypropyl cellulose Substances 0.000 description 1
- 235000010977 hydroxypropyl cellulose Nutrition 0.000 description 1
- 239000001866 hydroxypropyl methyl cellulose Substances 0.000 description 1
- 229920003088 hydroxypropyl methyl cellulose Polymers 0.000 description 1
- 235000010979 hydroxypropyl methyl cellulose Nutrition 0.000 description 1
- UFVKGYZPFZQRLF-UHFFFAOYSA-N hydroxypropyl methyl cellulose Chemical compound OC1C(O)C(OC)OC(CO)C1OC1C(O)C(O)C(OC2C(C(O)C(OC3C(C(O)C(O)C(CO)O3)O)C(CO)O2)O)C(CO)O1 UFVKGYZPFZQRLF-UHFFFAOYSA-N 0.000 description 1
- 230000001900 immune effect Effects 0.000 description 1
- 230000028993 immune response Effects 0.000 description 1
- 102000018358 immunoglobulin Human genes 0.000 description 1
- 229940072221 immunoglobulins Drugs 0.000 description 1
- 238000007449 liver function test Methods 0.000 description 1
- 210000004698 lymphocyte Anatomy 0.000 description 1
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- 229920003145 methacrylic acid copolymer Polymers 0.000 description 1
- 229940117841 methacrylic acid copolymer Drugs 0.000 description 1
- 231100000957 no side effect Toxicity 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 1
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- HQAITFAUVZBHNB-UHFFFAOYSA-N sodium;pentahydrate Chemical compound O.O.O.O.O.[Na] HQAITFAUVZBHNB-UHFFFAOYSA-N 0.000 description 1
- 235000014347 soups Nutrition 0.000 description 1
- 238000010254 subcutaneous injection Methods 0.000 description 1
- 239000007929 subcutaneous injection Substances 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 230000001629 suppression Effects 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 208000024891 symptom Diseases 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
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 210000001738 temporomandibular joint Anatomy 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
Classifications
-
- 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
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/44—Non condensed pyridines; Hydrogenated derivatives 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
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- Chemical & Material Sciences (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Rheumatology (AREA)
- Pain & Pain Management (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP416180A JPS56100719A (en) | 1980-01-17 | 1980-01-17 | Antirheumatic agent |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE3010751A1 true DE3010751A1 (de) | 1981-08-06 |
| DE3010751C2 DE3010751C2 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1989-05-11 |
Family
ID=11577010
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19803010751 Granted DE3010751A1 (de) | 1980-01-17 | 1980-03-20 | Verwendung von 9-chlor-7-(1h-tetrazol-5-yl)-5-oxo-5h(1h) benzopyrano(2,3-b) pyridin und seinen salzen und hydraten bei der behandlung von rheumatischen beschwerden |
Country Status (4)
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1984001711A1 (en) * | 1982-10-30 | 1984-05-10 | Yoshitomi Pharmaceutical | Hypotensives |
| JPH0217715U (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) * | 1988-07-18 | 1990-02-06 |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5516432B2 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) * | 1974-05-28 | 1980-05-01 |
-
1980
- 1980-01-17 JP JP416180A patent/JPS56100719A/ja active Granted
- 1980-03-14 IT IT20678/80A patent/IT1130970B/it active
- 1980-03-20 DE DE19803010751 patent/DE3010751A1/de active Granted
- 1980-04-14 US US06/139,624 patent/US4281001A/en not_active Expired - Lifetime
Non-Patent Citations (1)
| Title |
|---|
| NICHTS ERMITTELT * |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS634523B2 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1988-01-29 |
| DE3010751C2 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1989-05-11 |
| US4281001A (en) | 1981-07-28 |
| IT8020678A0 (it) | 1980-03-14 |
| IT1130970B (it) | 1986-06-18 |
| JPS56100719A (en) | 1981-08-12 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8110 | Request for examination paragraph 44 | ||
| D2 | Grant after examination | ||
| 8328 | Change in the person/name/address of the agent |
Free format text: VOSSIUS, V., DIPL.-CHEM. DR.RER.NAT. TAUCHNER, P., DIPL.-CHEM. DR.RER.NAT. HEUNEMANN, D., DIPL.-PHYS. DR.RER.NAT. RAUH, P., DIPL.-CHEM. DR.RER.NAT., PAT.-ANWAELTE, 8000 MUENCHEN |
|
| 8364 | No opposition during term of opposition | ||
| 8339 | Ceased/non-payment of the annual fee |