CA1079195A - Procede de preparation d'un nouveau medicament hypotenseur a action retardee - Google Patents
Procede de preparation d'un nouveau medicament hypotenseur a action retardeeInfo
- Publication number
- CA1079195A CA1079195A CA261,673A CA261673A CA1079195A CA 1079195 A CA1079195 A CA 1079195A CA 261673 A CA261673 A CA 261673A CA 1079195 A CA1079195 A CA 1079195A
- Authority
- CA
- Canada
- Prior art keywords
- wax
- amino
- drug compositions
- guanidine
- hydroxy
- 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
- 230000003111 delayed effect Effects 0.000 title claims description 6
- 239000002220 antihypertensive agent Substances 0.000 title claims description 5
- 238000002360 preparation method Methods 0.000 title 1
- 239000000203 mixture Substances 0.000 claims abstract description 29
- 239000002253 acid Substances 0.000 claims abstract description 12
- 235000014113 dietary fatty acids Nutrition 0.000 claims abstract description 7
- 239000000194 fatty acid Substances 0.000 claims abstract description 7
- 229930195729 fatty acid Natural products 0.000 claims abstract description 7
- 150000004665 fatty acids Chemical class 0.000 claims abstract description 7
- 150000002009 diols Chemical class 0.000 claims abstract description 5
- 150000003839 salts Chemical class 0.000 claims abstract description 5
- QKIQJNNDIWGVEH-UHFFFAOYSA-N guanoxabenz Chemical compound ONC(=N)NN=CC1=C(Cl)C=CC=C1Cl QKIQJNNDIWGVEH-UHFFFAOYSA-N 0.000 claims abstract description 4
- 239000003814 drug Substances 0.000 claims description 10
- 229940079593 drug Drugs 0.000 claims description 9
- -1 2,6-dichlorobenzylidene-amino Chemical group 0.000 claims description 8
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 8
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 7
- WFBHRSAKANVBKH-UHFFFAOYSA-N N-hydroxyguanidine Chemical compound NC(=N)NO WFBHRSAKANVBKH-UHFFFAOYSA-N 0.000 claims description 6
- 150000007513 acids Chemical class 0.000 claims description 5
- 125000004432 carbon atom Chemical group C* 0.000 claims description 5
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 4
- 229910052799 carbon Inorganic materials 0.000 claims description 4
- IHEJEKZAKSNRLY-UHFFFAOYSA-N nonacosanoic acid Chemical compound CCCCCCCCCCCCCCCCCCCCCCCCCCCCC(O)=O IHEJEKZAKSNRLY-UHFFFAOYSA-N 0.000 claims description 4
- 125000004429 atom Chemical group 0.000 claims description 3
- 229910052500 inorganic mineral Inorganic materials 0.000 claims description 2
- 239000011707 mineral Substances 0.000 claims description 2
- 239000003925 fat Substances 0.000 claims 1
- 230000001077 hypotensive effect Effects 0.000 abstract description 5
- 208000001953 Hypotension Diseases 0.000 abstract description 2
- 208000021822 hypotensive Diseases 0.000 abstract description 2
- 239000003826 tablet Substances 0.000 description 15
- 239000001993 wax Substances 0.000 description 9
- 239000000546 pharmaceutical excipient Substances 0.000 description 8
- ZRALSGWEFCBTJO-UHFFFAOYSA-N Guanidine Chemical compound NC(N)=N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 description 6
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 6
- 230000000694 effects Effects 0.000 description 5
- 206010020772 Hypertension Diseases 0.000 description 4
- GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 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 3
- CHJJGSNFBQVOTG-UHFFFAOYSA-N N-methyl-guanidine Natural products CNC(N)=N CHJJGSNFBQVOTG-UHFFFAOYSA-N 0.000 description 3
- WNROFYMDJYEPJX-UHFFFAOYSA-K aluminium hydroxide Chemical compound [OH-].[OH-].[OH-].[Al+3] WNROFYMDJYEPJX-UHFFFAOYSA-K 0.000 description 3
- 230000036772 blood pressure Effects 0.000 description 3
- 239000008119 colloidal silica Substances 0.000 description 3
- SWSQBOPZIKWTGO-UHFFFAOYSA-N dimethylaminoamidine Natural products CN(C)C(N)=N SWSQBOPZIKWTGO-UHFFFAOYSA-N 0.000 description 3
- 239000008101 lactose Substances 0.000 description 3
- 235000021355 Stearic acid Nutrition 0.000 description 2
- 238000010521 absorption reaction Methods 0.000 description 2
- METKIMKYRPQLGS-UHFFFAOYSA-N atenolol Chemical compound CC(C)NCC(O)COC1=CC=C(CC(N)=O)C=C1 METKIMKYRPQLGS-UHFFFAOYSA-N 0.000 description 2
- 238000000338 in vitro Methods 0.000 description 2
- 150000002500 ions Chemical class 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 2
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 2
- 239000008117 stearic acid Substances 0.000 description 2
- HFGHRUCCKVYFKL-UHFFFAOYSA-N 4-ethoxy-2-piperazin-1-yl-7-pyridin-4-yl-5h-pyrimido[5,4-b]indole Chemical compound C1=C2NC=3C(OCC)=NC(N4CCNCC4)=NC=3C2=CC=C1C1=CC=NC=C1 HFGHRUCCKVYFKL-UHFFFAOYSA-N 0.000 description 1
- 244000215068 Acacia senegal Species 0.000 description 1
- 201000001320 Atherosclerosis Diseases 0.000 description 1
- 208000007530 Essential hypertension Diseases 0.000 description 1
- 229920000084 Gum arabic Polymers 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- 208000004880 Polyuria Diseases 0.000 description 1
- 206010048302 Tubulointerstitial nephritis Diseases 0.000 description 1
- 239000004164 Wax ester Substances 0.000 description 1
- 239000000205 acacia gum Substances 0.000 description 1
- 235000010489 acacia gum Nutrition 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 210000001367 artery Anatomy 0.000 description 1
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid group Chemical group C(C1=CC=CC=C1)(=O)O WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 1
- CDQSJQSWAWPGKG-UHFFFAOYSA-N butane-1,1-diol Chemical compound CCCC(O)O CDQSJQSWAWPGKG-UHFFFAOYSA-N 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 208000020450 carbohydrate metabolism disease Diseases 0.000 description 1
- 230000000747 cardiac effect Effects 0.000 description 1
- 231100000850 chronic interstitial nephritis Toxicity 0.000 description 1
- 229940110456 cocoa butter Drugs 0.000 description 1
- 235000019868 cocoa butter Nutrition 0.000 description 1
- 230000001079 digestive effect Effects 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 230000035619 diuresis Effects 0.000 description 1
- 229940088679 drug related substance Drugs 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 235000011167 hydrochloric acid Nutrition 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 230000001631 hypertensive effect Effects 0.000 description 1
- 239000007943 implant Substances 0.000 description 1
- 208000017745 inborn carbohydrate metabolic disease Diseases 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 230000009245 menopause Effects 0.000 description 1
- 239000012170 montan wax Substances 0.000 description 1
- 230000002746 orthostatic effect Effects 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- ULWHHBHJGPPBCO-UHFFFAOYSA-N propane-1,1-diol Chemical compound CCC(O)O ULWHHBHJGPPBCO-UHFFFAOYSA-N 0.000 description 1
- 230000033764 rhythmic process Effects 0.000 description 1
- 238000007127 saponification reaction Methods 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 230000009278 visceral effect Effects 0.000 description 1
- 235000019386 wax ester Nutrition 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/20—Pills, tablets, discs, rods
- A61K9/2004—Excipients; Inactive ingredients
- A61K9/2013—Organic compounds, e.g. phospholipids, fats
-
- 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
- A61K31/13—Amines
- A61K31/155—Amidines (), e.g. guanidine (H2N—C(=NH)—NH2), isourea (N=C(OH)—NH2), isothiourea (—N=C(SH)—NH2)
Landscapes
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Molecular Biology (AREA)
- Biophysics (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR7528940A FR2324294A1 (fr) | 1975-09-22 | 1975-09-22 | Nouveau medicament hypotenseur a action retardee, ainsi que le procede de preparation de ce nouveau medicament |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1079195A true CA1079195A (fr) | 1980-06-10 |
Family
ID=9160270
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA261,673A Expired CA1079195A (fr) | 1975-09-22 | 1976-09-21 | Procede de preparation d'un nouveau medicament hypotenseur a action retardee |
Country Status (14)
| Country | Link |
|---|---|
| JP (1) | JPS5241239A (enExample) |
| AU (1) | AU506061B2 (enExample) |
| BE (1) | BE846399A (enExample) |
| CA (1) | CA1079195A (enExample) |
| DE (1) | DE2641988C2 (enExample) |
| FR (1) | FR2324294A1 (enExample) |
| GB (1) | GB1521594A (enExample) |
| GR (1) | GR63149B (enExample) |
| IE (1) | IE44387B1 (enExample) |
| IL (1) | IL50458A (enExample) |
| NL (1) | NL7610344A (enExample) |
| NZ (1) | NZ182128A (enExample) |
| PT (1) | PT65618B (enExample) |
| ZA (1) | ZA765640B (enExample) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US8148429B2 (en) | 2000-08-07 | 2012-04-03 | Anamar Ab | Use of benzylideneaminoguanidines and hydroxyguanidines as melanocortin receptor ligands |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB0019359D0 (en) | 2000-08-07 | 2000-09-27 | Melacure Therapeutics Ab | Novel guanidines |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CH537370A (de) * | 1968-01-22 | 1973-05-31 | Sandoz Ag | Verfahren zur Herstellung neuer Guanidin-Derivate |
| US3621056A (en) * | 1968-08-16 | 1971-11-16 | Sandoz Ag | Substituted benzylideneamino guanidines |
| US3857933A (en) * | 1969-10-17 | 1974-12-31 | Hoechst Ag | Process for the manufacture of a drug dosage form permitting controlled release of active ingredient |
-
1975
- 1975-09-22 FR FR7528940A patent/FR2324294A1/fr active Granted
-
1976
- 1976-09-10 IL IL50458A patent/IL50458A/xx unknown
- 1976-09-16 NL NL7610344A patent/NL7610344A/xx active Search and Examination
- 1976-09-17 DE DE2641988A patent/DE2641988C2/de not_active Expired
- 1976-09-21 CA CA261,673A patent/CA1079195A/fr not_active Expired
- 1976-09-21 PT PT65618A patent/PT65618B/pt unknown
- 1976-09-21 GB GB39109/76A patent/GB1521594A/en not_active Expired
- 1976-09-21 IE IE2088/76A patent/IE44387B1/en unknown
- 1976-09-21 NZ NZ182128A patent/NZ182128A/xx unknown
- 1976-09-21 GR GR51741A patent/GR63149B/el unknown
- 1976-09-21 BE BE170785A patent/BE846399A/xx not_active IP Right Cessation
- 1976-09-21 ZA ZA765640A patent/ZA765640B/xx unknown
- 1976-09-21 AU AU17963/76A patent/AU506061B2/en not_active Expired
- 1976-09-22 JP JP51113214A patent/JPS5241239A/ja active Pending
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US8148429B2 (en) | 2000-08-07 | 2012-04-03 | Anamar Ab | Use of benzylideneaminoguanidines and hydroxyguanidines as melanocortin receptor ligands |
| US8309609B2 (en) | 2000-08-07 | 2012-11-13 | Anamar Ab | Use of benzylideneaminoguanidines and hydroxyguanidines as melanocortin receptor ligands |
| US8410174B2 (en) | 2000-08-07 | 2013-04-02 | Anamar Ab | Method for treating arthritis |
| US9227927B2 (en) | 2000-08-07 | 2016-01-05 | Anamar Ab | Method of treating inflammation |
Also Published As
| Publication number | Publication date |
|---|---|
| FR2324294B1 (enExample) | 1979-09-14 |
| FR2324294A1 (fr) | 1977-04-15 |
| IL50458A (en) | 1981-02-27 |
| IE44387L (en) | 1977-03-22 |
| NL7610344A (nl) | 1977-03-24 |
| GR63149B (en) | 1979-09-25 |
| AU1796376A (en) | 1978-04-06 |
| GB1521594A (en) | 1978-08-16 |
| DE2641988A1 (de) | 1977-03-24 |
| AU506061B2 (en) | 1979-12-13 |
| NZ182128A (en) | 1978-09-25 |
| IE44387B1 (en) | 1981-11-18 |
| DE2641988C2 (de) | 1986-04-03 |
| IL50458A0 (en) | 1976-11-30 |
| ZA765640B (en) | 1977-10-26 |
| BE846399A (fr) | 1977-03-21 |
| JPS5241239A (en) | 1977-03-30 |
| PT65618B (fr) | 1978-07-04 |
| PT65618A (fr) | 1976-10-01 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKEX | Expiry |