FR4727M - La l.hydroxyproline et ses associations médicamenteuses dans le traitement des maladies rhumatismales. - Google Patents
La l.hydroxyproline et ses associations médicamenteuses dans le traitement des maladies rhumatismales. Download PDFInfo
- Publication number
- FR4727M FR4727M FR37265A FR37265A FR4727M FR 4727 M FR4727 M FR 4727M FR 37265 A FR37265 A FR 37265A FR 37265 A FR37265 A FR 37265A FR 4727 M FR4727 M FR 4727M
- Authority
- FR
- France
- Prior art keywords
- hydroxyproline
- glucosamine
- treatment
- rheumatic diseases
- drug combinations
- 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
- 229960002591 hydroxyproline Drugs 0.000 title description 20
- PMMYEEVYMWASQN-DMTCNVIQSA-N Hydroxyproline Chemical compound O[C@H]1CN[C@H](C(O)=O)C1 PMMYEEVYMWASQN-DMTCNVIQSA-N 0.000 title description 19
- PMMYEEVYMWASQN-UHFFFAOYSA-N dl-hydroxyproline Natural products OC1C[NH2+]C(C([O-])=O)C1 PMMYEEVYMWASQN-UHFFFAOYSA-N 0.000 title description 19
- FGMPLJWBKKVCDB-UHFFFAOYSA-N trans-L-hydroxy-proline Natural products ON1CCCC1C(O)=O FGMPLJWBKKVCDB-UHFFFAOYSA-N 0.000 title description 19
- 208000025747 Rheumatic disease Diseases 0.000 title description 7
- 239000000890 drug combination Substances 0.000 title description 2
- MSWZFWKMSRAUBD-UHFFFAOYSA-N beta-D-galactosamine Natural products NC1C(O)OC(CO)C(O)C1O MSWZFWKMSRAUBD-UHFFFAOYSA-N 0.000 description 13
- 229960002442 glucosamine Drugs 0.000 description 13
- MSWZFWKMSRAUBD-IVMDWMLBSA-N 2-amino-2-deoxy-D-glucopyranose Chemical compound N[C@H]1C(O)O[C@H](CO)[C@@H](O)[C@@H]1O MSWZFWKMSRAUBD-IVMDWMLBSA-N 0.000 description 12
- 239000003435 antirheumatic agent Substances 0.000 description 8
- 229940079593 drug Drugs 0.000 description 4
- 239000003814 drug Substances 0.000 description 4
- 230000000552 rheumatic effect Effects 0.000 description 4
- 229960001911 glucosamine hydrochloride Drugs 0.000 description 3
- 239000000546 pharmaceutical excipient Substances 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- CBOJBBMQJBVCMW-BTVCFUMJSA-N (2r,3r,4s,5r)-2-amino-3,4,5,6-tetrahydroxyhexanal;hydrochloride Chemical compound Cl.O=C[C@H](N)[C@@H](O)[C@H](O)[C@H](O)CO CBOJBBMQJBVCMW-BTVCFUMJSA-N 0.000 description 2
- CDAWCLOXVUBKRW-UHFFFAOYSA-N 2-aminophenol Chemical compound NC1=CC=CC=C1O CDAWCLOXVUBKRW-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 206010061218 Inflammation Diseases 0.000 description 2
- 241001465754 Metazoa Species 0.000 description 2
- 125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 description 2
- 230000003110 anti-inflammatory effect Effects 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 230000004054 inflammatory process Effects 0.000 description 2
- 231100001231 less toxic Toxicity 0.000 description 2
- -1 n - butyl Chemical group 0.000 description 2
- 230000003285 pharmacodynamic effect Effects 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 230000001225 therapeutic effect Effects 0.000 description 2
- RLQZIECDMISZHS-UHFFFAOYSA-N 2-phenylcyclohexa-2,5-diene-1,4-dione Chemical compound O=C1C=CC(=O)C(C=2C=CC=CC=2)=C1 RLQZIECDMISZHS-UHFFFAOYSA-N 0.000 description 1
- WZQSFHYYVUHUNU-UHFFFAOYSA-N 4-butylpyrazolidine Chemical compound CCCCC1CNNC1 WZQSFHYYVUHUNU-UHFFFAOYSA-N 0.000 description 1
- BSYNRYMUTXBXSQ-FOQJRBATSA-N 59096-14-9 Chemical compound CC(=O)OC1=CC=CC=C1[14C](O)=O BSYNRYMUTXBXSQ-FOQJRBATSA-N 0.000 description 1
- RLFWWDJHLFCNIJ-UHFFFAOYSA-N Aminoantipyrine Natural products CN1C(C)=C(N)C(=O)N1C1=CC=CC=C1 RLFWWDJHLFCNIJ-UHFFFAOYSA-N 0.000 description 1
- RMMXTBMQSGEXHJ-UHFFFAOYSA-N Aminophenazone Chemical compound O=C1C(N(C)C)=C(C)N(C)N1C1=CC=CC=C1 RMMXTBMQSGEXHJ-UHFFFAOYSA-N 0.000 description 1
- BSYNRYMUTXBXSQ-UHFFFAOYSA-N Aspirin Chemical compound CC(=O)OC1=CC=CC=C1C(O)=O BSYNRYMUTXBXSQ-UHFFFAOYSA-N 0.000 description 1
- 229920000742 Cotton Polymers 0.000 description 1
- IIUZTXTZRGLYTI-UHFFFAOYSA-N Dihydrogriseofulvin Natural products COC1CC(=O)CC(C)C11C(=O)C(C(OC)=CC(OC)=C2Cl)=C2O1 IIUZTXTZRGLYTI-UHFFFAOYSA-N 0.000 description 1
- 241000790917 Dioxys <bee> Species 0.000 description 1
- UXWOXTQWVMFRSE-UHFFFAOYSA-N Griseoviridin Natural products O=C1OC(C)CC=C(C(NCC=CC=CC(O)CC(O)C2)=O)SCC1NC(=O)C1=COC2=N1 UXWOXTQWVMFRSE-UHFFFAOYSA-N 0.000 description 1
- 241000699670 Mus sp. Species 0.000 description 1
- DDUHZTYCFQRHIY-UHFFFAOYSA-N Negwer: 6874 Natural products COC1=CC(=O)CC(C)C11C(=O)C(C(OC)=CC(OC)=C2Cl)=C2O1 DDUHZTYCFQRHIY-UHFFFAOYSA-N 0.000 description 1
- 206010034464 Periarthritis Diseases 0.000 description 1
- 241000779819 Syncarpia glomulifera Species 0.000 description 1
- 229960001138 acetylsalicylic acid Drugs 0.000 description 1
- 229960000212 aminophenazone Drugs 0.000 description 1
- 230000000202 analgesic effect Effects 0.000 description 1
- VEQOALNAAJBPNY-UHFFFAOYSA-N antipyrine Chemical compound CN1C(C)=CC(=O)N1C1=CC=CC=C1 VEQOALNAAJBPNY-UHFFFAOYSA-N 0.000 description 1
- 206010003246 arthritis Diseases 0.000 description 1
- 210000001188 articular cartilage Anatomy 0.000 description 1
- 235000010290 biphenyl Nutrition 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- 125000006267 biphenyl group Chemical group 0.000 description 1
- 210000001185 bone marrow Anatomy 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- DDUHZTYCFQRHIY-RBHXEPJQSA-N griseofulvin Chemical compound COC1=CC(=O)C[C@@H](C)[C@@]11C(=O)C(C(OC)=CC(OC)=C2Cl)=C2O1 DDUHZTYCFQRHIY-RBHXEPJQSA-N 0.000 description 1
- 229960002867 griseofulvin Drugs 0.000 description 1
- XXSMGPRMXLTPCZ-UHFFFAOYSA-N hydroxychloroquine Chemical compound ClC1=CC=C2C(NC(C)CCCN(CCO)CC)=CC=NC2=C1 XXSMGPRMXLTPCZ-UHFFFAOYSA-N 0.000 description 1
- 229960004171 hydroxychloroquine Drugs 0.000 description 1
- 125000004464 hydroxyphenyl group Chemical group 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 230000002045 lasting effect Effects 0.000 description 1
- 238000002483 medication Methods 0.000 description 1
- 229940126601 medicinal product Drugs 0.000 description 1
- 239000008188 pellet Substances 0.000 description 1
- 229960005222 phenazone Drugs 0.000 description 1
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 1
- 229960002895 phenylbutazone Drugs 0.000 description 1
- 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 1
- 208000001297 phlebitis Diseases 0.000 description 1
- 239000001739 pinus spp. Substances 0.000 description 1
- 230000003389 potentiating effect Effects 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- USPWKWBDZOARPV-UHFFFAOYSA-N pyrazolidine Chemical compound C1CNNC1 USPWKWBDZOARPV-UHFFFAOYSA-N 0.000 description 1
- 201000003068 rheumatic fever Diseases 0.000 description 1
- 206010039073 rheumatoid arthritis Diseases 0.000 description 1
- 150000003873 salicylate salts Chemical class 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 208000011580 syndromic disease Diseases 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 229940036248 turpentine Drugs 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
- A61K31/70—Carbohydrates; Sugars; Derivatives thereof
- A61K31/7004—Monosaccharides having only carbon, hydrogen and oxygen atoms
-
- 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
- A61K31/40—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil
-
- 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
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
- A61K31/415—1,2-Diazoles
-
- 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
-
- 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
- A61K31/60—Salicylic acid; Derivatives thereof
-
- 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
- A61K31/60—Salicylic acid; Derivatives thereof
- A61K31/618—Salicylic acid; Derivatives thereof having the carboxyl group in position 1 esterified, e.g. salsalate
- A61K31/621—Salicylic acid; Derivatives thereof having the carboxyl group in position 1 esterified, e.g. salsalate having the hydroxy group in position 2 esterified, e.g. benorylate
-
- 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
- A61K31/70—Carbohydrates; Sugars; Derivatives thereof
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K35/00—Medicinal preparations containing materials or reaction products thereof with undetermined constitution
- A61K35/12—Materials from mammals; Compositions comprising non-specified tissues or cells; Compositions comprising non-embryonic stem cells; Genetically modified cells
- A61K35/28—Bone marrow; Haematopoietic stem cells; Mesenchymal stem cells of any origin, e.g. adipose-derived stem cells
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/04—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D207/10—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no 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
- C07D207/16—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
Landscapes
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Epidemiology (AREA)
- Pharmacology & Pharmacy (AREA)
- Medicinal Chemistry (AREA)
- Organic Chemistry (AREA)
- Immunology (AREA)
- Developmental Biology & Embryology (AREA)
- Molecular Biology (AREA)
- Cell Biology (AREA)
- Zoology (AREA)
- Virology (AREA)
- Biotechnology (AREA)
- Biomedical Technology (AREA)
- Engineering & Computer Science (AREA)
- Hematology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Description
REPUBLIQUE FRANÇAISE
MINISTERE DE L'INDUSTRIE
SERVICE de la PROPRIÉTÉ INDUSTRIELLE
BREVET SPÉCIAL DE MÉDICAMENT
P.V. n° 37.265 Classification internationale
N° 4.727 M A 61k
La 1 . hydroxyproline et ses associations médicamenteuses dans 1 etraWëHfôïîfif de s maladies rhumatismales. (Invention : J.-C. Denis et J. Rambaud.) HGINDCV;
14» m h h oh h
! I I I chaoh-c—c—c—c-cho I I I ! oh oh h nh2
cehiaosn = 179,17
La l.hydroxyproline a pour formule :
ho
\
hc h2c
-ch2
I
ch
\n
COO-
c5h903n = 131,13
Propriétés pharmacodynamiques. — Le chlorhydrate de glucosamine et la l.hydroxyproline ont été administrés chez l'animal, respectivement à la dose de 150 et 15 mg/kg, dans les différents tests servant habituellement à mesurer l'action analgésique et l'action anti-inflammatoire des médicaments. Parmi ceux-ci citons notamment le syndrome de torsion provoqué chez la souris par la phényl-benzoquinone, l'inhibition de la douleur provoquée par l'inflammation expérimentale de la patte du rat, l'inflammation provoquée par les pellets de coton ou l'injection d'essence de térébenthine.
Le chlorhydrate de glucosamine et la l.hydroxyproline ont également été administrés à l'animal en association avec les antirhumatismaux connus et notamment :
Acide acétylsalicylique et salicylates;
Acétyl p.aminophénol ;
Phényl - 1 - diméthyl - 2 - 3 - isopyrazolone (antipyrine) ;
7 210551 7 •+. prix du fascicule
Société dite : TECPAN S. A. résidant au Mexique.
Demandé le 4 novembre 1965, à 15h 3m, à l'aris.
Délivré par arrêté du 2 janvier 1967. [
{Bulletin officiel de la Propriété industrielle [5.5.M.], n° 6 du 6 février 1967.)
La présente invention consiste en l'utilisation de la l.hydroxyproline en association :
- Avec la glucosamine (ou un de ses sels comme chlorhydrate) ;
Ou avec un médicament antirhumastimal ;
Ou avec la glucosamine et un médicament anti-rhumatismal.
La glucosamine a pour formule :
3,5 - dioxo -
Phényl - 1 - diméthyl^' 2*^"3 '- diméthylamino - 4 pyrazolone (amidopyrine) ;
Dioxy - 3,5 diphényl - 1,2 n - butyl - 4 - pyrazo-lidine (phénylbutazone) ;
1 - phényl - 2(p.hydroxyphényl)
4 - n - butyl - pyrazolidine ;
Griséofulvine ;
Hydroxychloroquine ;
Extrait de cartilage articulaire et de moelle osseuse.
Les tests pharmacodynamiques ont mis en évidence :
1° L'intérêt d'employer simultanément la glucosamine avec la l.hydroxyproline pour obtenir un , effet anti-inflammatoi're ;
2° L'intérêt d'adjoindre à la l.hydroxyproline ou à l'association glucosamine - l.hydroxyproline, un médicament antirhumatismal, tel que ceux cités plus haut, si l'on désire obtenir un effet plus rapide et plus important.
En effet, la l.hydroxyproline et plus encore l'association glucosamine-hydroxyproline non seulement potentialisent les effets des médicaments antirhumatismaux mais aussi prolongent leur action dans le temps et permettent de les employer, pour une même efficacité, à des doses plus faibles et donc moins toxiques.
Applications thérapeutiques. — La l.hydroxyproline et l'association glucosamine - l.hydroxyproline peuvent être utilisées avec succès dans les différentes affections rhumatismales, soit seules soit simultanément avec les autres médications connues, selon les exemples ci-dessous :
Chl. de glucosamine, g 0,200
1. hydroxyproline, g, 0,020
Excipient q.s. pour un comprimé.
4 à 6 comprimés par jour comme fond des affections rhumatismales ;
traitement de b. Acétyl p. aminophénol, g 0,400
l.hydroxyproline, g 0,010
2 francs
[4.727 M]
4 à 6 comprimés par jour, dans les algies rhumatismales ;
c. Acide acétylsalicylique, g 0,250
Chl. de glucosamine, g 0,150
1. hydroxyproline, g 0,015
Excipient q.s. pour un comprimé.
6 comprimés par jour, dans toutes les algies rhumatismales ;
■d. Dioxy- ,3,5 -diphényl-1,2 -re-butyl-4- 0,100 pyrazolidine, g.
Chl. de glucosamine, g 0,100
1. hydroxyproline, g 0,010
Excipient q.s. pour un comprimé.
1 à 2 comprimés par jour dans les cas de rhumatisme articulaire aigu, polyarthrite rhumatoïde, arthrose, périarthrite, phlébite.
Formes pharmaceutiques. — La glucosamine, ou l'un de ses sels comme le chlorhydrate de glucosamine, et la l.hydroxyproline pourront être utilisés :
Soit en solution sous une présentation pharma-ceutiquement acceptable comme les ampoules injectables ou buvables, les sirops, les solutions;
Soit à l'état de poudre sous une présentation pharmaceutiquement acceptable qui pourra être celle de comprimés, gélules, sachets, granulés, suppositoires, seuls ou en association avec d'autres médicaments ou composés pharmaceutiquement acceptables.
RÉSUMÉ
1° La présente invention a pour objet l'utilisation de la l.hydroxyproline en association avec la glucosamine (ou un de ses sels comme le chlorhydrate), ou avec un médicament antirhumatismal, ou avec la glucosamine et un médicament antirhumatismal, dans le traitement des maladies rhumatismales.
2° L'adjonction de la l.hydroxyproline et plus encore de l'association l.hydroxyproline-chl. de glucosamine à un médicament antirhumatismal détermine une activité thérapeutique plus importante, plus durable et moins toxique que celle que l'on aurait obtenue 'avec le produit antirhumatismal administré isolément.
Société dite : TECPAN S. A.
Par procuration :
Blétry
AVIS DOCUMENTAIRE SUR LA NOUVEAUTÉ
Documents susceptibles de porter atteinte à la nouveauté du médicament : néant.
Documents illustrant l'état de la technique en la matière : néant.
Pour la vente des fascicules, s'adresser à I'Imprimerie Nationale, 27, rue de la Convention, Paris (15e).
Priority Applications (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR37265A FR4727M (fr) | 1965-11-04 | 1965-11-04 | La l.hydroxyproline et ses associations médicamenteuses dans le traitement des maladies rhumatismales. |
| BE688490A BE688490A (fr) | 1965-11-04 | 1966-10-19 | La 1.hydroxyproline et ses associations médicamenteuses dans le traitement des maladies du tissu conjonctif. |
| NL6615581A NL6615581A (nl) | 1965-11-04 | 1966-11-04 | Werkwijze voor het bereiden van een therapeutisch preparaat voor het behandelen van ziekten van het bindweefsel. |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR37265A FR4727M (fr) | 1965-11-04 | 1965-11-04 | La l.hydroxyproline et ses associations médicamenteuses dans le traitement des maladies rhumatismales. |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| FR4727M true FR4727M (fr) | 1967-02-06 |
Family
ID=8591826
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FR37265A Expired FR4727M (fr) | 1965-11-04 | 1965-11-04 | La l.hydroxyproline et ses associations médicamenteuses dans le traitement des maladies rhumatismales. |
Country Status (3)
| Country | Link |
|---|---|
| BE (1) | BE688490A (fr) |
| FR (1) | FR4727M (fr) |
| NL (1) | NL6615581A (fr) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0740938A3 (fr) * | 1995-05-05 | 1997-03-12 | Ipr Inst Pharm Res Riehen Ag | Proline et hydroxy-4-proline comme agents thérapeutiques |
| EP1356811A4 (fr) * | 2001-01-05 | 2005-08-17 | Kyowa Hakko Kogyo Kk | Agents prophylactiques ou remedes contre l'arthrite |
-
1965
- 1965-11-04 FR FR37265A patent/FR4727M/fr not_active Expired
-
1966
- 1966-10-19 BE BE688490A patent/BE688490A/fr not_active IP Right Cessation
- 1966-11-04 NL NL6615581A patent/NL6615581A/xx unknown
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0740938A3 (fr) * | 1995-05-05 | 1997-03-12 | Ipr Inst Pharm Res Riehen Ag | Proline et hydroxy-4-proline comme agents thérapeutiques |
| EP1356811A4 (fr) * | 2001-01-05 | 2005-08-17 | Kyowa Hakko Kogyo Kk | Agents prophylactiques ou remedes contre l'arthrite |
| US7138386B2 (en) | 2001-01-05 | 2006-11-21 | Kyowa Hakko Kogyo Co., Ltd. | Preventives or remedies for arthritis |
Also Published As
| Publication number | Publication date |
|---|---|
| BE688490A (fr) | 1967-03-31 |
| NL6615581A (nl) | 1967-05-05 |
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