DE2520818A1 - Pharmazeutische zubereitungen, enthaltend ein chinolinderivat - Google Patents
Pharmazeutische zubereitungen, enthaltend ein chinolinderivatInfo
- Publication number
- DE2520818A1 DE2520818A1 DE19752520818 DE2520818A DE2520818A1 DE 2520818 A1 DE2520818 A1 DE 2520818A1 DE 19752520818 DE19752520818 DE 19752520818 DE 2520818 A DE2520818 A DE 2520818A DE 2520818 A1 DE2520818 A1 DE 2520818A1
- Authority
- DE
- Germany
- Prior art keywords
- amino
- salt
- contain
- dihydroxypropyloxycarbonyl
- phenyl
- 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.)
- Withdrawn
Links
- 239000000825 pharmaceutical preparation Substances 0.000 title claims description 7
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical class N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 title 1
- 150000003839 salts Chemical class 0.000 claims description 21
- 238000002360 preparation method Methods 0.000 claims description 15
- 239000002253 acid Substances 0.000 claims description 14
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 12
- KWIUHFFTVRNATP-UHFFFAOYSA-N glycine betaine Chemical compound C[N+](C)(C)CC([O-])=O KWIUHFFTVRNATP-UHFFFAOYSA-N 0.000 claims description 8
- 150000007513 acids Chemical class 0.000 claims description 7
- 150000001875 compounds Chemical class 0.000 claims description 7
- 229960003403 betaine hydrochloride Drugs 0.000 claims description 6
- HOPSCVCBEOCPJZ-UHFFFAOYSA-N carboxymethyl(trimethyl)azanium;chloride Chemical compound [Cl-].C[N+](C)(C)CC(O)=O HOPSCVCBEOCPJZ-UHFFFAOYSA-N 0.000 claims description 6
- APQPGQGAWABJLN-UHFFFAOYSA-N Floctafenine Chemical compound OCC(O)COC(=O)C1=CC=CC=C1NC1=CC=NC2=C(C(F)(F)F)C=CC=C12 APQPGQGAWABJLN-UHFFFAOYSA-N 0.000 claims description 5
- 229960003237 betaine Drugs 0.000 claims description 4
- PINGOEJCFIYTDQ-UHFFFAOYSA-N 2,3-dihydroxypropyl 2-[2-amino-8-(trifluoromethyl)quinolin-4-yl]benzoate Chemical compound OC(COC(=O)C1=C(C=CC=C1)C1=CC(=NC2=C(C=CC=C12)C(F)(F)F)N)CO PINGOEJCFIYTDQ-UHFFFAOYSA-N 0.000 claims description 3
- 239000003814 drug Substances 0.000 claims description 3
- 239000000203 mixture Substances 0.000 claims description 3
- 150000003862 amino acid derivatives Chemical class 0.000 claims description 2
- 150000001413 amino acids Chemical class 0.000 claims description 2
- 229940079593 drug Drugs 0.000 claims description 2
- 238000000034 method Methods 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims 1
- 230000001225 therapeutic effect Effects 0.000 claims 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 18
- 230000000202 analgesic effect Effects 0.000 description 6
- 241001465754 Metazoa Species 0.000 description 3
- 241000700159 Rattus Species 0.000 description 3
- KPGXRSRHYNQIFN-UHFFFAOYSA-N 2-oxoglutaric acid Chemical compound OC(=O)CCC(=O)C(O)=O KPGXRSRHYNQIFN-UHFFFAOYSA-N 0.000 description 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
- 241000699666 Mus <mouse, genus> Species 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 230000007059 acute toxicity Effects 0.000 description 2
- 231100000403 acute toxicity Toxicity 0.000 description 2
- 239000011324 bead Substances 0.000 description 2
- -1 dihydroxypropyloxycarbonyl Chemical group 0.000 description 2
- 239000007928 intraperitoneal injection Substances 0.000 description 2
- 238000011835 investigation Methods 0.000 description 2
- 230000000144 pharmacologic effect Effects 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 208000011580 syndromic disease Diseases 0.000 description 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
- WGUGHMBECREKMG-UHFFFAOYSA-N 8-(trifluoromethyl)quinolin-2-amine Chemical compound C1=CC=C(C(F)(F)F)C2=NC(N)=CC=C21 WGUGHMBECREKMG-UHFFFAOYSA-N 0.000 description 1
- 208000004998 Abdominal Pain Diseases 0.000 description 1
- 229910002012 Aerosil® Inorganic materials 0.000 description 1
- 208000006820 Arthralgia Diseases 0.000 description 1
- 208000008035 Back Pain Diseases 0.000 description 1
- 229920000084 Gum arabic Polymers 0.000 description 1
- 208000007514 Herpes zoster Diseases 0.000 description 1
- 208000008930 Low Back Pain Diseases 0.000 description 1
- KDXKERNSBIXSRK-UHFFFAOYSA-N Lysine Natural products NCCCCC(N)C(O)=O KDXKERNSBIXSRK-UHFFFAOYSA-N 0.000 description 1
- 239000004472 Lysine Substances 0.000 description 1
- 208000019695 Migraine disease Diseases 0.000 description 1
- 241000699670 Mus sp. Species 0.000 description 1
- 208000000112 Myalgia Diseases 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- 206010037660 Pyrexia Diseases 0.000 description 1
- 208000025747 Rheumatic disease Diseases 0.000 description 1
- 241000978776 Senegalia senegal Species 0.000 description 1
- 235000010489 acacia gum Nutrition 0.000 description 1
- 239000000205 acacia gum Substances 0.000 description 1
- HWXBTNAVRSUOJR-UHFFFAOYSA-N alpha-hydroxyglutaric acid Natural products OC(=O)C(O)CCC(O)=O HWXBTNAVRSUOJR-UHFFFAOYSA-N 0.000 description 1
- 229940009533 alpha-ketoglutaric acid Drugs 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 239000000730 antalgic agent Substances 0.000 description 1
- 230000037396 body weight Effects 0.000 description 1
- 229940075614 colloidal silicon dioxide Drugs 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 208000015181 infectious disease Diseases 0.000 description 1
- 230000002458 infectious effect Effects 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- 229940098779 methanesulfonic acid Drugs 0.000 description 1
- 208000013465 muscle pain Diseases 0.000 description 1
- 208000004296 neuralgia Diseases 0.000 description 1
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 150000003248 quinolines Chemical class 0.000 description 1
- 238000012453 sprague-dawley rat model Methods 0.000 description 1
- 150000003460 sulfonic acids Chemical class 0.000 description 1
- 208000004371 toothache Diseases 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 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
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
- A61K31/47—Quinolines; Isoquinolines
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (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)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR7416018A FR2269944B1 (enExample) | 1974-05-09 | 1974-05-09 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2520818A1 true DE2520818A1 (de) | 1975-11-20 |
Family
ID=9138625
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19752520818 Withdrawn DE2520818A1 (de) | 1974-05-09 | 1975-05-09 | Pharmazeutische zubereitungen, enthaltend ein chinolinderivat |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US3988459A (enExample) |
| BE (1) | BE828818A (enExample) |
| CA (1) | CA1043262A (enExample) |
| DE (1) | DE2520818A1 (enExample) |
| DK (1) | DK200275A (enExample) |
| FR (1) | FR2269944B1 (enExample) |
| GB (1) | GB1507180A (enExample) |
| IE (1) | IE41053B1 (enExample) |
| NL (1) | NL7505459A (enExample) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR100779419B1 (ko) | 2005-07-26 | 2007-11-30 | 대한민국 | 중독성이 경감된 진통제 |
-
1974
- 1974-05-09 FR FR7416018A patent/FR2269944B1/fr not_active Expired
-
1975
- 1975-05-06 US US05/575,023 patent/US3988459A/en not_active Expired - Lifetime
- 1975-05-07 DK DK200275A patent/DK200275A/da unknown
- 1975-05-07 BE BE156134A patent/BE828818A/xx unknown
- 1975-05-08 CA CA226,516A patent/CA1043262A/fr not_active Expired
- 1975-05-08 GB GB19488/75A patent/GB1507180A/en not_active Expired
- 1975-05-09 IE IE1051/75A patent/IE41053B1/xx unknown
- 1975-05-09 NL NL7505459A patent/NL7505459A/xx not_active Application Discontinuation
- 1975-05-09 DE DE19752520818 patent/DE2520818A1/de not_active Withdrawn
Also Published As
| Publication number | Publication date |
|---|---|
| IE41053B1 (en) | 1979-10-10 |
| US3988459A (en) | 1976-10-26 |
| GB1507180A (en) | 1978-04-12 |
| FR2269944B1 (enExample) | 1978-02-03 |
| DK200275A (da) | 1975-11-10 |
| NL7505459A (nl) | 1975-11-11 |
| BE828818A (fr) | 1975-11-07 |
| IE41053L (en) | 1975-11-09 |
| CA1043262A (fr) | 1978-11-28 |
| FR2269944A1 (enExample) | 1975-12-05 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8141 | Disposal/no request for examination |