GB2171302A - Therapeutic hydroxyprolines - Google Patents
Therapeutic hydroxyprolines Download PDFInfo
- Publication number
- GB2171302A GB2171302A GB08527159A GB8527159A GB2171302A GB 2171302 A GB2171302 A GB 2171302A GB 08527159 A GB08527159 A GB 08527159A GB 8527159 A GB8527159 A GB 8527159A GB 2171302 A GB2171302 A GB 2171302A
- Authority
- GB
- United Kingdom
- Prior art keywords
- proline
- medicament
- cis
- amino acids
- 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.)
- Granted
Links
- PMMYEEVYMWASQN-DMTCNVIQSA-N Hydroxyproline Chemical class O[C@H]1CN[C@H](C(O)=O)C1 PMMYEEVYMWASQN-DMTCNVIQSA-N 0.000 title claims abstract description 22
- 230000001225 therapeutic effect Effects 0.000 title claims description 3
- 229940024606 amino acid Drugs 0.000 claims abstract description 31
- 235000001014 amino acid Nutrition 0.000 claims abstract description 31
- 150000001413 amino acids Chemical class 0.000 claims abstract description 31
- FGMPLJWBKKVCDB-UHFFFAOYSA-N trans-L-hydroxy-proline Natural products ON1CCCC1C(O)=O FGMPLJWBKKVCDB-UHFFFAOYSA-N 0.000 claims abstract description 29
- PMMYEEVYMWASQN-UHFFFAOYSA-N dl-hydroxyproline Natural products OC1C[NH2+]C(C([O-])=O)C1 PMMYEEVYMWASQN-UHFFFAOYSA-N 0.000 claims abstract description 27
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 claims abstract description 26
- PMMYEEVYMWASQN-IMJSIDKUSA-N cis-4-Hydroxy-L-proline Chemical compound O[C@@H]1CN[C@H](C(O)=O)C1 PMMYEEVYMWASQN-IMJSIDKUSA-N 0.000 claims abstract description 20
- 229960002591 hydroxyproline Drugs 0.000 claims abstract description 19
- ONIBWKKTOPOVIA-BYPYZUCNSA-N L-Proline Chemical compound OC(=O)[C@@H]1CCCN1 ONIBWKKTOPOVIA-BYPYZUCNSA-N 0.000 claims abstract description 16
- 229960002429 proline Drugs 0.000 claims abstract description 16
- ONIBWKKTOPOVIA-UHFFFAOYSA-N Proline Natural products OC(=O)C1CCCN1 ONIBWKKTOPOVIA-UHFFFAOYSA-N 0.000 claims abstract description 15
- 239000004471 Glycine Substances 0.000 claims abstract description 13
- LCWXJXMHJVIJFK-UHFFFAOYSA-N Hydroxylysine Natural products NCC(O)CC(N)CC(O)=O LCWXJXMHJVIJFK-UHFFFAOYSA-N 0.000 claims abstract description 13
- QNAYBMKLOCPYGJ-REOHCLBHSA-N L-alanine Chemical compound C[C@H](N)C(O)=O QNAYBMKLOCPYGJ-REOHCLBHSA-N 0.000 claims abstract description 13
- KZSNJWFQEVHDMF-BYPYZUCNSA-N L-valine Chemical compound CC(C)[C@H](N)C(O)=O KZSNJWFQEVHDMF-BYPYZUCNSA-N 0.000 claims abstract description 13
- KZSNJWFQEVHDMF-UHFFFAOYSA-N Valine Natural products CC(C)C(N)C(O)=O KZSNJWFQEVHDMF-UHFFFAOYSA-N 0.000 claims abstract description 13
- 235000004279 alanine Nutrition 0.000 claims abstract description 13
- YSMODUONRAFBET-UHFFFAOYSA-N delta-DL-hydroxylysine Natural products NCC(O)CCC(N)C(O)=O YSMODUONRAFBET-UHFFFAOYSA-N 0.000 claims abstract description 13
- 201000010099 disease Diseases 0.000 claims abstract description 13
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 13
- YSMODUONRAFBET-UHNVWZDZSA-N erythro-5-hydroxy-L-lysine Chemical compound NC[C@H](O)CC[C@H](N)C(O)=O YSMODUONRAFBET-UHNVWZDZSA-N 0.000 claims abstract description 13
- QJHBJHUKURJDLG-UHFFFAOYSA-N hydroxy-L-lysine Natural products NCCCCC(NO)C(O)=O QJHBJHUKURJDLG-UHFFFAOYSA-N 0.000 claims abstract description 13
- 239000004474 valine Substances 0.000 claims abstract description 13
- 201000009030 Carcinoma Diseases 0.000 claims abstract description 12
- KDXKERNSBIXSRK-YFKPBYRVSA-N L-lysine Chemical compound NCCCC[C@H](N)C(O)=O KDXKERNSBIXSRK-YFKPBYRVSA-N 0.000 claims abstract description 12
- 239000004472 Lysine Substances 0.000 claims abstract description 12
- KDXKERNSBIXSRK-UHFFFAOYSA-N Lysine Natural products NCCCCC(N)C(O)=O KDXKERNSBIXSRK-UHFFFAOYSA-N 0.000 claims abstract description 12
- 210000004204 blood vessel Anatomy 0.000 claims abstract description 8
- 230000003612 virological effect Effects 0.000 claims abstract description 5
- BJBUEDPLEOHJGE-DMTCNVIQSA-N cis-3-hydroxy-L-proline Chemical compound O[C@@H]1CC[NH2+][C@@H]1C([O-])=O BJBUEDPLEOHJGE-DMTCNVIQSA-N 0.000 claims abstract description 4
- 239000008298 dragée Substances 0.000 claims abstract description 3
- 102000004196 processed proteins & peptides Human genes 0.000 claims abstract description 3
- 108090000765 processed proteins & peptides Proteins 0.000 claims abstract description 3
- 206010028980 Neoplasm Diseases 0.000 claims description 37
- 239000003814 drug Substances 0.000 claims description 25
- 150000001875 compounds Chemical class 0.000 claims description 20
- 238000000034 method Methods 0.000 claims description 16
- 201000011510 cancer Diseases 0.000 claims description 14
- 238000002560 therapeutic procedure Methods 0.000 claims description 12
- 210000004027 cell Anatomy 0.000 claims description 10
- 230000037396 body weight Effects 0.000 claims description 8
- 210000004292 cytoskeleton Anatomy 0.000 claims description 8
- 206010003571 Astrocytoma Diseases 0.000 claims description 4
- 238000010171 animal model Methods 0.000 claims description 4
- 229910052799 carbon Inorganic materials 0.000 claims description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- 238000001990 intravenous administration Methods 0.000 claims description 4
- LEVWYRKDKASIDU-QWWZWVQMSA-N D-cystine Chemical compound OC(=O)[C@H](N)CSSC[C@@H](N)C(O)=O LEVWYRKDKASIDU-QWWZWVQMSA-N 0.000 claims description 3
- XUJNEKJLAYXESH-REOHCLBHSA-N L-Cysteine Chemical compound SC[C@H](N)C(O)=O XUJNEKJLAYXESH-REOHCLBHSA-N 0.000 claims description 3
- 235000018417 cysteine Nutrition 0.000 claims description 3
- XUJNEKJLAYXESH-UHFFFAOYSA-N cysteine Natural products SCC(N)C(O)=O XUJNEKJLAYXESH-UHFFFAOYSA-N 0.000 claims description 3
- 229960003067 cystine Drugs 0.000 claims description 3
- DYLIWHYUXAJDOJ-OWOJBTEDSA-N (e)-4-(6-aminopurin-9-yl)but-2-en-1-ol Chemical compound NC1=NC=NC2=C1N=CN2C\C=C\CO DYLIWHYUXAJDOJ-OWOJBTEDSA-N 0.000 claims description 2
- 208000003174 Brain Neoplasms Diseases 0.000 claims description 2
- 102000010834 Extracellular Matrix Proteins Human genes 0.000 claims description 2
- 108010037362 Extracellular Matrix Proteins Proteins 0.000 claims description 2
- 206010027476 Metastases Diseases 0.000 claims description 2
- 208000036142 Viral infection Diseases 0.000 claims description 2
- 210000002469 basement membrane Anatomy 0.000 claims description 2
- 238000004113 cell culture Methods 0.000 claims description 2
- 230000032823 cell division Effects 0.000 claims description 2
- 210000002808 connective tissue Anatomy 0.000 claims description 2
- 239000000470 constituent Substances 0.000 claims description 2
- 230000000694 effects Effects 0.000 claims description 2
- 210000002744 extracellular matrix Anatomy 0.000 claims description 2
- 210000005260 human cell Anatomy 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
- 230000001900 immune effect Effects 0.000 claims description 2
- 210000004692 intercellular junction Anatomy 0.000 claims description 2
- 208000017169 kidney disease Diseases 0.000 claims description 2
- 230000000877 morphologic effect Effects 0.000 claims description 2
- 208000007538 neurilemmoma Diseases 0.000 claims description 2
- 230000008506 pathogenesis Effects 0.000 claims description 2
- 230000008092 positive effect Effects 0.000 claims description 2
- 210000001519 tissue Anatomy 0.000 claims description 2
- 231100000331 toxic Toxicity 0.000 claims description 2
- 230000002588 toxic effect Effects 0.000 claims description 2
- 210000004881 tumor cell Anatomy 0.000 claims description 2
- 230000009385 viral infection Effects 0.000 claims description 2
- 229930182821 L-proline Natural products 0.000 claims 1
- -1 line Chemical compound 0.000 claims 1
- 230000000926 neurological effect Effects 0.000 claims 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
- A61K31/40—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
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
Landscapes
- Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical & Material Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Organic Chemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Epidemiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Pyrrole Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Peptides Or Proteins (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Cosmetics (AREA)
Abstract
Cis-4-hydroxy-L-proline or cis-3-hydroxy-L-proline are used in the treatment of carcinomas, diseases of the blood vessels and viral diseases. The hydroxyproline is administered intravenously as a solution or orally in tablets or dragees either with or without the other amino acids proline, valine, alanine, lysine, hydroxylysine and glycine. The hydroxyproline or the other amino acids can be in free form or in acetylated form or as peptides.
Description
SPECIFICATION
Tumor therapy
The main subject of this application is a new therapy for cancer especially carcinomas and related tumors. The expression "related tumors" means tumors which are like carcinomas of an embryologically epithelial origin. Examples are astrocytomas, neurinomas, suprarenal (medulla) tumors and so on.
In the years 1933 - 1946 Helen M. Dyer of the
United States National Cancer Institute administered a wide range of amino acids in experimental tumors of the mouse. Among others she mentioned hydroxyproline, but it is known that results of experimental animal tumors are scarcely transferable to human cancer.
In the last about 20 years electronmicroscopic device have shown the existence of the so called cytoskeleton within the cells. Immunological methods applied on the cytoskeleton are today used to recognize the origin of a cancer in their metastases. Applicant's concept, however, goes farther and postulates that a disturbance of the cytoskeleton is an essential factor for the pathogenesis of cancer, especially carcinomas. When in cancer cells and tissues the cytoskeleton, the cell junctions, the basal laminas and the filaments of the extra-cellular matrix, the connective tissues additionally are out of order it is doubtless indicated to substitute the constituents of these filamental systems-which are specific amino acids.
From this point of view one of the most important of these amino acids is hydroxyproline. Here, however, it is not sufficient to differentiate between L and D configuration as Dyer had done.
The decisive act is to differentiate also between cis and trans isomers of hydroxyproline which arises of the asymmetrical nature of the hydroxyl-group bearing carbon atom (this carbon atom is preferably number 4, but also number 3 is to be considered).
The proof that that is so was established by tests which were performed according to applicant's suggestion. These were not tests on experimental animal tumors which are scarcely transferable in their results to native human cancer. They were performed in human cell culture, the cells of which were removed from brain tumor patient by neurosurgery. The administering of L cis - Hydroxyproline to these astrocytoma tumor cells brought about not only a considerably slowed rate of cell division but also induced morphological redifferentiation, that is the cells resembled no longer tumor but normal astroglial cells. On the other side the trans isomer of L-4-Hydroxyproline showed not at all any positive effects.
Hydroxyproline may be given alone or combined with other amino acids which are occuring in the above named filamental system as there are proline, valine, alanine, lysine, hydroxylysine, glycine, cysteine and cystine.
The administration of such compounds however is not restricted to cancer cases alone, but is also indicated in cases of viral infection and blood vessels disease. Even neurologicai and rheumatological indications are marking out.
The administering of amino acids in their free form is a possible method. Their specific effect however can also be brought into existence by administering compounds containing these amino acids that is for examples in acetylated form or as corresponding peptides. That means the administering of the named amino acids can be directly or indirectly.
Amino acids are scarcely toxic at all, therefore the named compounds have a wide doses range.
However as with ail amino acids therapy the known contraindications should wherever possible be excluded, especially patients with renal diseases.
The therapeutic administering of these compounds is principally the same as with all amino acid therapy. Tabletts or dragees for oral, solutions for intravenous (or central intravenous) administering. Dosis range for hydroxyproline is 0,01 - 0,1 g daily (in severe cases up to 0,2 g daily) per kg of the patient's body weight. Dosis range for hydroxyproline combined with proline, valine, alanine, lysine, hydroxylysine and glycine is for hydroxyproline 0,006 - 0,06 g and 0,003 / 0,03 g for each of the other amino acid, per kg of the patient's body weight, daily.
1. A medicament containing cis hdyroxy - L proline
2. A medicament containing cis hydroxy - L proline in combination with proline, valine, alanine, lysine, hydroxylysine and glycine.
3. A method of treating carcinomas and related tumors by administering cis hydroxy - L - proline 0,01 - 0,2 g/kg daily.
4. A method of treating bloodvessels diseases by administering cis hydroxy - L - proline 0,01 - 0,2 g/kg daily.
5. A method of treating viral diseases by administering cis hydroxy - L - proline 0,01 - 0,2 g/kg daily.
6. The methods of claims 3, 4 and 5 where cis hydroxy-L proline 0,006 - 0,06 is combined with proline, valine, alanine, lysine, hydroxylysine and glycine 0,003 - 0,3 g/kg of each.
7. Cis-4-hydroxy-L-proline for use in a method for the treatment of the human body by therapy.
8. Cis-3-hydroxy-L-proline for use in a method for the treatment of the human body by therapy.
9. The compound claimed in Claim 1 or Claim 2 in a medicament comprising also the amino acids proline, valine, alanine, lysine, hydroxylysine and glycine.
10. Use of the compound as claimed in Claim 7 or 8, in the preparation of a medicament for the treatment of carcinomas or related tumours.
11. Use of the compound as claimed in Claim 7 or 8 in the preparation of a medicament for the treatment of diseases of the blood vessels.
12. Use of the compound as claimed in Claim 7
**WARNING** end of DESC field may overlap start of CLMS **.
Claims (13)
1. A medicament containing cis hdyroxy - L proline
2. A medicament containing cis hydroxy - L proline in combination with proline, valine, alanine, lysine, hydroxylysine and glycine.
3. A method of treating carcinomas and related tumors by administering cis hydroxy - L - proline 0,01 - 0,2 g/kg daily.
4. A method of treating bloodvessels diseases by administering cis hydroxy - L - proline 0,01 - 0,2 g/kg daily.
5. A method of treating viral diseases by administering cis hydroxy - L - proline 0,01 - 0,2 g/kg daily.
6. The methods of claims 3, 4 and 5 where cis hydroxy-L proline 0,006 - 0,06 is combined with proline, valine, alanine, lysine, hydroxylysine and glycine 0,003 - 0,3 g/kg of each.
7. Cis-4-hydroxy-L-proline for use in a method for the treatment of the human body by therapy.
8. Cis-3-hydroxy-L-proline for use in a method for the treatment of the human body by therapy.
9. The compound claimed in Claim 1 or Claim 2 in a medicament comprising also the amino acids proline, valine, alanine, lysine, hydroxylysine and glycine.
10. Use of the compound as claimed in Claim 7 or 8, in the preparation of a medicament for the treatment of carcinomas or related tumours.
11. Use of the compound as claimed in Claim 7 or 8 in the preparation of a medicament for the treatment of diseases of the blood vessels.
12. Use of the compound as claimed in Claim 7 or 8 in the preparation of a medicament for the treatment of viral diseases.
13. The preparation according to any claim of claims 1 to 10 substantially as herein described.
13. Use of the compound as claimed in Claim 10, 11 or 12 in which the medicament also contains the amino acids proline, valine, alanine, line, hydroxylysine and glycine.
14. Use of the compound as claimed in Claim 10, 11 or 12 in which the daily dose is 0.01 to 0.2 gramme per kilogramme of the patient's body weight.
15. Use of the compound as claimed in Claim 13 in which the daily dose is 0.006 to 0.06 gramme of the hydroxyproline and 0.003 to 0.3 gramme of each of the additional amino acids per kilogramme of the patient's body weight.
New claims or amendments to claims filed on 6
May 1986
New or amended claims:- 1 to 13
1. Use of cis-4-hydroxy-L-proline in the preparation of a medicament for the treatment of carcinomas or related tumours.
2. Use of cis-4-hydroxy-L-proline in the preparation of a medicament for the treatment of diseases of the blood vessels.
3. Use of cis-4-hydroxy-L-proiine in the preparation of a medicament for the treatment of viral diseases.
4. Use of cis-4-hydroxy-L-proline in the preparation of a medicament for the treatment of neurological conditions.
5. Use of cis-4-hydroxy-L-proline in the preparation of a medicament for the treatment of rheumatological conditions.
6. The preparation of a medicament as claimed in any preceding claim using cis-3-hydroxy-L-proline instead of cis-4-hydroxy/ L-proline.
7. The preparation of a medicament according to any preceding claim, the medicament also comprising the amino acids proline, valine, alanine, lysine, hydroxylysine, glycine, cysteine and cystine.
8. The preparation of a medicament according to any claim of claims 1 to 6 in which the daily dose is 0.01 to 0.2 gramme per kilogramme of the patient's body weight.
9. The preparation of a medicament according to claim 7, in which the daily dose is 0.006 to 0.06 gramme of the hydroxyproline and 0.003 to 0.3 gramme of each of the additional amino acids per kilogramme of the patient's body weight.
10. The preparation of a medicament according to any preceding claim, in which the hydroxyproline or the other amino acids when present are each in the form of a derived compound.
11. A medicament made by the preparation according to any preceding claim.
12. A medicament according to claim 11, substantially as herein described.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US66820084A | 1984-11-05 | 1984-11-05 | |
| US72356585A | 1985-04-15 | 1985-04-15 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| GB8527159D0 GB8527159D0 (en) | 1985-12-11 |
| GB2171302A true GB2171302A (en) | 1986-08-28 |
| GB2171302B GB2171302B (en) | 1989-08-23 |
Family
ID=27099851
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB8527159A Expired GB2171302B (en) | 1984-11-05 | 1985-11-04 | Tumour therapy |
Country Status (5)
| Country | Link |
|---|---|
| JP (1) | JPH0723309B2 (en) |
| CA (1) | CA1281288C (en) |
| CH (1) | CH667591A5 (en) |
| DE (1) | DE3538619C2 (en) |
| GB (1) | GB2171302B (en) |
Cited By (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1987004925A1 (en) * | 1986-02-18 | 1987-08-27 | Biota Scientific Management Pty. Ltd. | Stimulation of angiogenesis |
| EP0307390A3 (en) * | 1987-09-04 | 1991-04-10 | Merckle Gmbh | Chemical compound consisting of cis-3-hydroxyproline for therapeutic treatment, and process for its preparation |
| EP0740938A3 (en) * | 1995-05-05 | 1997-03-12 | Ipr Inst Pharm Res Riehen Ag | Proline and 4-hydroxyproline as therapeutic agents |
| WO1997038690A1 (en) * | 1996-04-16 | 1997-10-23 | Chephasaar Chem.-Pharm. Fabrik Gmbh | Agent for inhibiting leukocyte invasion of tissues |
| US6066665A (en) * | 1996-03-11 | 2000-05-23 | Hoerrmann; Wilhelm | Combination of cis-4-hydroxy-L-proline and N-methyl-cis-4-hydroxy-L-proline for use as a therapeutic agent, in particular in cancer treatment |
| WO2005056006A1 (en) * | 2003-12-12 | 2005-06-23 | Salama Zoser B | Use of chp as an inhibitor of glutathione s-transferases and collagen iv |
| WO2005120495A1 (en) * | 2004-06-14 | 2005-12-22 | Salama Zoser B | Anti-cancer composition comprising proline or its derivatives and an anti-tumour antibody |
| US8940791B2 (en) | 2005-11-11 | 2015-01-27 | Signature R&D Holdings, Llc | Acetylated amino acids as anti-platelet agents, nutritional and vitamin supplements |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3728852C2 (en) * | 1987-08-28 | 2003-06-18 | Wilhelm Hoerrmann | Medicines for tumor therapy |
| DE10359828A1 (en) * | 2003-12-12 | 2005-07-28 | Zoser B. Dr.Rer.Nat. Salama | CHP gemcitabine combination agents and their use as antitumor agents, in particular anti-metastatic agents |
| UA82753C2 (en) * | 2003-12-18 | 2008-05-12 | Цозер Б. Салама | Proline derivatives used as pharmaceutical active ingredients for the treatment of tumours |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1246141A (en) * | 1967-09-14 | 1971-09-15 | Paul Coirre | Improvements in or relating to -hydroxylproline derivatives |
| GB1399887A (en) * | 1971-06-10 | 1975-07-02 | Prockop D J | Composition and methods for controlling collagen synthesis |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3932638A (en) * | 1967-09-14 | 1976-01-13 | Franco-Chimie S.A.R.L. | Compositions and methods for wound healing |
| FR2207702B1 (en) * | 1972-11-23 | 1975-11-28 | Rhone Poulenc Ind | |
| JPS59164718A (en) * | 1983-03-10 | 1984-09-17 | Advance Res & Dev Co Ltd | Preventive for cancer |
-
1985
- 1985-10-24 CA CA000493821A patent/CA1281288C/en not_active Expired - Lifetime
- 1985-10-29 CH CH4616/85A patent/CH667591A5/en not_active IP Right Cessation
- 1985-10-30 DE DE3538619A patent/DE3538619C2/en not_active Expired - Lifetime
- 1985-11-04 GB GB8527159A patent/GB2171302B/en not_active Expired
- 1985-11-05 JP JP24642585A patent/JPH0723309B2/en not_active Expired - Fee Related
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1246141A (en) * | 1967-09-14 | 1971-09-15 | Paul Coirre | Improvements in or relating to -hydroxylproline derivatives |
| GB1399887A (en) * | 1971-06-10 | 1975-07-02 | Prockop D J | Composition and methods for controlling collagen synthesis |
Cited By (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1987004925A1 (en) * | 1986-02-18 | 1987-08-27 | Biota Scientific Management Pty. Ltd. | Stimulation of angiogenesis |
| EP0307390A3 (en) * | 1987-09-04 | 1991-04-10 | Merckle Gmbh | Chemical compound consisting of cis-3-hydroxyproline for therapeutic treatment, and process for its preparation |
| EP0740938A3 (en) * | 1995-05-05 | 1997-03-12 | Ipr Inst Pharm Res Riehen Ag | Proline and 4-hydroxyproline as therapeutic agents |
| US5827874A (en) * | 1995-05-05 | 1998-10-27 | Meyer; Hans | Methods of treating pain and inflammation with proline |
| US6066665A (en) * | 1996-03-11 | 2000-05-23 | Hoerrmann; Wilhelm | Combination of cis-4-hydroxy-L-proline and N-methyl-cis-4-hydroxy-L-proline for use as a therapeutic agent, in particular in cancer treatment |
| WO1997038690A1 (en) * | 1996-04-16 | 1997-10-23 | Chephasaar Chem.-Pharm. Fabrik Gmbh | Agent for inhibiting leukocyte invasion of tissues |
| WO2005056006A1 (en) * | 2003-12-12 | 2005-06-23 | Salama Zoser B | Use of chp as an inhibitor of glutathione s-transferases and collagen iv |
| WO2005120495A1 (en) * | 2004-06-14 | 2005-12-22 | Salama Zoser B | Anti-cancer composition comprising proline or its derivatives and an anti-tumour antibody |
| US7727530B2 (en) | 2004-06-14 | 2010-06-01 | Salama Zoser B | Anti-cancer composition comprising proline or its derivatives and an anti-tumour antibody |
| US8940791B2 (en) | 2005-11-11 | 2015-01-27 | Signature R&D Holdings, Llc | Acetylated amino acids as anti-platelet agents, nutritional and vitamin supplements |
Also Published As
| Publication number | Publication date |
|---|---|
| GB2171302B (en) | 1989-08-23 |
| CH667591A5 (en) | 1988-10-31 |
| DE3538619A1 (en) | 1986-05-07 |
| DE3538619C2 (en) | 1995-11-09 |
| JPH0723309B2 (en) | 1995-03-15 |
| JPS61155324A (en) | 1986-07-15 |
| GB8527159D0 (en) | 1985-12-11 |
| CA1281288C (en) | 1991-03-12 |
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