DE10008159B4 - Verwendung von 2-Methyl-thiazolidin-2,4-dicarbonsäure und/oder ihrer physiologisch verträglichen Salze als Antikrebsmittel - Google Patents
Verwendung von 2-Methyl-thiazolidin-2,4-dicarbonsäure und/oder ihrer physiologisch verträglichen Salze als Antikrebsmittel Download PDFInfo
- Publication number
- DE10008159B4 DE10008159B4 DE10008159A DE10008159A DE10008159B4 DE 10008159 B4 DE10008159 B4 DE 10008159B4 DE 10008159 A DE10008159 A DE 10008159A DE 10008159 A DE10008159 A DE 10008159A DE 10008159 B4 DE10008159 B4 DE 10008159B4
- Authority
- DE
- Germany
- Prior art keywords
- dicarboxylic acid
- thiazolidine
- methyl
- mtdc
- acetylcysteine
- 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 - Fee Related
Links
- JCAKCGQZNBEITC-UHFFFAOYSA-N 2-methyl-1,3-thiazolidine-2,4-dicarboxylic acid Chemical compound OC(=O)C1(C)NC(C(O)=O)CS1 JCAKCGQZNBEITC-UHFFFAOYSA-N 0.000 title claims abstract description 60
- 150000003839 salts Chemical class 0.000 title claims abstract description 9
- 239000002246 antineoplastic agent Substances 0.000 title description 2
- 206010028980 Neoplasm Diseases 0.000 claims abstract description 28
- 201000011510 cancer Diseases 0.000 claims abstract description 13
- 238000011282 treatment Methods 0.000 claims abstract description 11
- 238000011321 prophylaxis Methods 0.000 claims description 6
- 206010058467 Lung neoplasm malignant Diseases 0.000 claims description 4
- 206010038389 Renal cancer Diseases 0.000 claims description 3
- 201000005202 lung cancer Diseases 0.000 claims description 3
- 208000020816 lung neoplasm Diseases 0.000 claims description 3
- 210000004072 lung Anatomy 0.000 claims description 2
- 208000008839 Kidney Neoplasms Diseases 0.000 claims 1
- 201000010982 kidney cancer Diseases 0.000 claims 1
- 230000002265 prevention Effects 0.000 abstract description 4
- RWSXRVCMGQZWBV-WDSKDSINSA-N glutathione Chemical compound OC(=O)[C@@H](N)CCC(=O)N[C@@H](CS)C(=O)NCC(O)=O RWSXRVCMGQZWBV-WDSKDSINSA-N 0.000 description 75
- PWKSKIMOESPYIA-BYPYZUCNSA-N L-N-acetyl-Cysteine Chemical compound CC(=O)N[C@@H](CS)C(O)=O PWKSKIMOESPYIA-BYPYZUCNSA-N 0.000 description 44
- 229960004308 acetylcysteine Drugs 0.000 description 44
- 229960003180 glutathione Drugs 0.000 description 37
- XUJNEKJLAYXESH-REOHCLBHSA-N L-Cysteine Chemical compound SC[C@H](N)C(O)=O XUJNEKJLAYXESH-REOHCLBHSA-N 0.000 description 36
- 108010024636 Glutathione Proteins 0.000 description 19
- 239000004201 L-cysteine Substances 0.000 description 18
- 235000013878 L-cysteine Nutrition 0.000 description 18
- 210000004027 cell Anatomy 0.000 description 11
- 230000000694 effects Effects 0.000 description 10
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- 230000002588 toxic effect Effects 0.000 description 7
- 210000004881 tumor cell Anatomy 0.000 description 7
- 239000003814 drug Substances 0.000 description 6
- PWKSKIMOESPYIA-UHFFFAOYSA-N 2-acetamido-3-sulfanylpropanoic acid Chemical compound CC(=O)NC(CS)C(O)=O PWKSKIMOESPYIA-UHFFFAOYSA-N 0.000 description 5
- LCTONWCANYUPML-UHFFFAOYSA-M Pyruvate Chemical compound CC(=O)C([O-])=O LCTONWCANYUPML-UHFFFAOYSA-M 0.000 description 5
- 230000015572 biosynthetic process Effects 0.000 description 5
- 229940079593 drug Drugs 0.000 description 5
- 239000001301 oxygen Substances 0.000 description 5
- 229910052760 oxygen Inorganic materials 0.000 description 5
- 239000002243 precursor Substances 0.000 description 5
- 229940076788 pyruvate Drugs 0.000 description 5
- 230000009467 reduction Effects 0.000 description 5
- 230000009471 action Effects 0.000 description 4
- 150000001413 amino acids Chemical class 0.000 description 4
- 239000000824 cytostatic agent Substances 0.000 description 4
- 230000001681 protective effect Effects 0.000 description 4
- 150000003548 thiazolidines Chemical class 0.000 description 4
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
- 241001465754 Metazoa Species 0.000 description 3
- 241000699670 Mus sp. Species 0.000 description 3
- 208000006265 Renal cell carcinoma Diseases 0.000 description 3
- 230000001028 anti-proliverative effect Effects 0.000 description 3
- 230000001332 colony forming effect Effects 0.000 description 3
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- 230000001085 cytostatic effect Effects 0.000 description 3
- 238000000338 in vitro Methods 0.000 description 3
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- 201000009546 lung large cell carcinoma Diseases 0.000 description 3
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- 230000003449 preventive effect Effects 0.000 description 3
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- 230000002829 reductive effect Effects 0.000 description 3
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- 238000012360 testing method Methods 0.000 description 3
- 230000001225 therapeutic effect Effects 0.000 description 3
- AOJJSUZBOXZQNB-VTZDEGQISA-N 4'-epidoxorubicin Chemical compound O([C@H]1C[C@@](O)(CC=2C(O)=C3C(=O)C=4C=CC=C(C=4C(=O)C3=C(O)C=21)OC)C(=O)CO)[C@H]1C[C@H](N)[C@@H](O)[C@H](C)O1 AOJJSUZBOXZQNB-VTZDEGQISA-N 0.000 description 2
- IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 description 2
- 241000894006 Bacteria Species 0.000 description 2
- 206010006187 Breast cancer Diseases 0.000 description 2
- 208000005623 Carcinogenesis Diseases 0.000 description 2
- HTIJFSOGRVMCQR-UHFFFAOYSA-N Epirubicin Natural products COc1cccc2C(=O)c3c(O)c4CC(O)(CC(OC5CC(N)C(=O)C(C)O5)c4c(O)c3C(=O)c12)C(=O)CO HTIJFSOGRVMCQR-UHFFFAOYSA-N 0.000 description 2
- LCTONWCANYUPML-UHFFFAOYSA-N Pyruvic acid Chemical compound CC(=O)C(O)=O LCTONWCANYUPML-UHFFFAOYSA-N 0.000 description 2
- 241000700159 Rattus Species 0.000 description 2
- 238000013459 approach Methods 0.000 description 2
- 230000036952 cancer formation Effects 0.000 description 2
- 231100000357 carcinogen Toxicity 0.000 description 2
- 231100000504 carcinogenesis Toxicity 0.000 description 2
- 239000003183 carcinogenic agent Substances 0.000 description 2
- 230000030833 cell death Effects 0.000 description 2
- 230000002490 cerebral effect Effects 0.000 description 2
- 230000006378 damage Effects 0.000 description 2
- 230000006735 deficit Effects 0.000 description 2
- 238000011161 development Methods 0.000 description 2
- 231100000673 dose–response relationship Toxicity 0.000 description 2
- 230000008030 elimination Effects 0.000 description 2
- 238000003379 elimination reaction Methods 0.000 description 2
- 229960001904 epirubicin Drugs 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 208000005017 glioblastoma Diseases 0.000 description 2
- 201000003911 head and neck carcinoma Diseases 0.000 description 2
- 238000001727 in vivo Methods 0.000 description 2
- 230000007246 mechanism Effects 0.000 description 2
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- 230000004962 physiological condition Effects 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 229940002612 prodrug Drugs 0.000 description 2
- 239000000651 prodrug Substances 0.000 description 2
- 102000004169 proteins and genes Human genes 0.000 description 2
- 230000001105 regulatory effect Effects 0.000 description 2
- 201000010174 renal carcinoma Diseases 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- 125000003396 thiol group Chemical group [H]S* 0.000 description 2
- 231100000419 toxicity Toxicity 0.000 description 2
- 230000001988 toxicity Effects 0.000 description 2
- OGYGFUAIIOPWQD-UHFFFAOYSA-N 1,3-thiazolidine Chemical compound C1CSCN1 OGYGFUAIIOPWQD-UHFFFAOYSA-N 0.000 description 1
- RZVAJINKPMORJF-UHFFFAOYSA-N Acetaminophen Chemical compound CC(=O)NC1=CC=C(O)C=C1 RZVAJINKPMORJF-UHFFFAOYSA-N 0.000 description 1
- 208000010507 Adenocarcinoma of Lung Diseases 0.000 description 1
- 208000007848 Alcoholism Diseases 0.000 description 1
- 206010005003 Bladder cancer Diseases 0.000 description 1
- 208000026310 Breast neoplasm Diseases 0.000 description 1
- 201000009030 Carcinoma Diseases 0.000 description 1
- 206010009944 Colon cancer Diseases 0.000 description 1
- 241000699800 Cricetinae Species 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 201000008808 Fibrosarcoma Diseases 0.000 description 1
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 1
- RWSXRVCMGQZWBV-UHFFFAOYSA-N L-Glutathione (reduced) Chemical compound OC(=O)C(N)CCC(=O)NC(CS)C(=O)NCC(O)=O RWSXRVCMGQZWBV-UHFFFAOYSA-N 0.000 description 1
- 241000699666 Mus <mouse, genus> Species 0.000 description 1
- IOVCWXUNBOPUCH-UHFFFAOYSA-M Nitrite anion Chemical compound [O-]N=O IOVCWXUNBOPUCH-UHFFFAOYSA-M 0.000 description 1
- 208000007097 Urinary Bladder Neoplasms Diseases 0.000 description 1
- 201000007930 alcohol dependence Diseases 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 230000036765 blood level Effects 0.000 description 1
- 230000037396 body weight Effects 0.000 description 1
- 210000004556 brain Anatomy 0.000 description 1
- 201000008274 breast adenocarcinoma Diseases 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 231100000457 cardiotoxic Toxicity 0.000 description 1
- 230000001451 cardiotoxic effect Effects 0.000 description 1
- 238000004113 cell culture Methods 0.000 description 1
- 210000000170 cell membrane Anatomy 0.000 description 1
- 230000002032 cellular defenses Effects 0.000 description 1
- 230000001413 cellular effect Effects 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000002512 chemotherapy Methods 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 230000000875 corresponding effect Effects 0.000 description 1
- 230000001120 cytoprotective effect Effects 0.000 description 1
- 210000000172 cytosol Anatomy 0.000 description 1
- 230000000254 damaging effect Effects 0.000 description 1
- 230000034994 death Effects 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 239000008298 dragée Substances 0.000 description 1
- 238000006911 enzymatic reaction Methods 0.000 description 1
- 239000008103 glucose Substances 0.000 description 1
- 201000000459 head and neck squamous cell carcinoma Diseases 0.000 description 1
- 230000002443 hepatoprotective effect Effects 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 230000000968 intestinal effect Effects 0.000 description 1
- 230000003834 intracellular effect Effects 0.000 description 1
- 238000007912 intraperitoneal administration Methods 0.000 description 1
- 210000004185 liver Anatomy 0.000 description 1
- 210000005228 liver tissue Anatomy 0.000 description 1
- 230000005923 long-lasting effect Effects 0.000 description 1
- 238000012153 long-term therapy Methods 0.000 description 1
- 230000007774 longterm Effects 0.000 description 1
- 231100000053 low toxicity Toxicity 0.000 description 1
- 201000005296 lung carcinoma Diseases 0.000 description 1
- 230000010534 mechanism of action Effects 0.000 description 1
- 239000002207 metabolite Substances 0.000 description 1
- 230000000510 mucolytic effect Effects 0.000 description 1
- 231100000350 mutagenesis Toxicity 0.000 description 1
- 231100000219 mutagenic Toxicity 0.000 description 1
- 230000003505 mutagenic effect Effects 0.000 description 1
- 231100000189 neurotoxic Toxicity 0.000 description 1
- 230000002887 neurotoxic effect Effects 0.000 description 1
- 150000002832 nitroso derivatives Chemical class 0.000 description 1
- 239000002674 ointment Substances 0.000 description 1
- 238000011275 oncology therapy Methods 0.000 description 1
- 210000000056 organ Anatomy 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- 229960005489 paracetamol Drugs 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 229940107700 pyruvic acid Drugs 0.000 description 1
- 239000003642 reactive oxygen metabolite Substances 0.000 description 1
- 230000008263 repair mechanism Effects 0.000 description 1
- 230000029058 respiratory gaseous exchange Effects 0.000 description 1
- 201000010153 skin papilloma Diseases 0.000 description 1
- 230000002269 spontaneous effect Effects 0.000 description 1
- 210000002784 stomach Anatomy 0.000 description 1
- 230000001629 suppression Effects 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 125000001984 thiazolidinyl group Chemical group 0.000 description 1
- 150000003573 thiols Chemical class 0.000 description 1
- 206010044285 tracheal cancer Diseases 0.000 description 1
- 238000002054 transplantation Methods 0.000 description 1
- 230000007723 transport mechanism Effects 0.000 description 1
- 230000004102 tricarboxylic acid cycle Effects 0.000 description 1
- 201000005112 urinary bladder cancer Diseases 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
- A61K31/41—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
- A61K31/425—Thiazoles
- A61K31/426—1,3-Thiazoles
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
Landscapes
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Epidemiology (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Thiazole And Isothizaole Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Priority Applications (17)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE10008159A DE10008159B4 (de) | 2000-02-15 | 2000-02-15 | Verwendung von 2-Methyl-thiazolidin-2,4-dicarbonsäure und/oder ihrer physiologisch verträglichen Salze als Antikrebsmittel |
| AU39190/01A AU783933B2 (en) | 2000-02-15 | 2001-02-15 | Use of 2-methyl-thiazolidin-2,4-dicarboxylic acid (2-MTDC) and/or physiologically compatible salts for treating and/or preventing cancers |
| EP01913699A EP1255538B1 (de) | 2000-02-15 | 2001-02-15 | Verwendung von 2-methyl-thiazolidin-2,4-dicarbonsäure und / oder ihrer physiologisch verträglichen salze zur herstellung eines medikaments zur behandlung von krebserkrankungen |
| DE50100833T DE50100833D1 (de) | 2000-02-15 | 2001-02-15 | Verwendung von 2-methyl-thiazolidin-2,4-dicarbonsäure und / oder ihrer physiologisch verträglichen salze zur herstellung eines medikaments zur behandlung von krebserkrankungen |
| PL01357179A PL357179A1 (en) | 2000-02-15 | 2001-02-15 | Use of 2-methyl-thiazolidin-2,4-dicarboxylic acid (2-mtdc) and/or physiologically compatible salts for treating and/or preventing cancers |
| PCT/DE2001/000656 WO2001060343A2 (de) | 2000-02-15 | 2001-02-15 | Verwendung von 2-methyl-thiazolidin-2,4-dicarbonsäure und/oder ihrer physiologisch verträglichen salze zur herstellung eines medikaments zur behandlung von krebserkrankungen |
| TR2003/02134T TR200302134T4 (tr) | 2000-02-15 | 2001-02-15 | 2-metil-tiazolidin-2,4-dikarboksilik asit ve/veya bunun fizyolojik olarak uygun tuzlarının anti-kanser ajanları olarak kullanımı. |
| CN01805095A CN1400899A (zh) | 2000-02-15 | 2001-02-15 | 2－甲基－噻唑烷－2,4－二甲酸和/或其生理上可耐受的盐作为抗癌剂的应用 |
| AT01913699T ATE252383T1 (de) | 2000-02-15 | 2001-02-15 | Verwendung von 2-methyl-thiazolidin-2,4- dicarbonsäure und / oder ihrer physiologisch verträglichen salze zur herstellung eines medikaments zur behandlung von krebserkrankungen |
| EA200200853A EA004592B1 (ru) | 2000-02-15 | 2001-02-15 | Применение 2-метилтиазолидин-3,3-дикарбоновой кислоты (2-мтдк) и/или ее физиологически совместимых солей для лечения и/или предупреждения рака |
| US10/182,442 US6943185B2 (en) | 2000-02-15 | 2001-02-15 | Use of 2-methyl-thiazolidine-2,4-dicarboxylic acid and/or physiologically compatible salts thereof for producing a medicament for treating cancers |
| PT01913699T PT1255538E (pt) | 2000-02-15 | 2001-02-15 | Utilizacao do acido 2-metil-tiazolidin-2,4-dicarboxilico e/ou sais compativeis fisiologicamente para tratamento e/ou prevencao de cancros |
| ES01913699T ES2208571T3 (es) | 2000-02-15 | 2001-02-15 | Utilizacion del acido 2-metil-tiazolidina-2,4-dicarboxilico y/o de sus sales fisiologicamente compatibles, como agente anticanceroso. |
| CA002399709A CA2399709C (en) | 2000-02-15 | 2001-02-15 | Use of 2-methyl-thiazolidin-2,4-dicarboxylic acid and/or physiologically compatible salts thereof for producing a medicament for treating cancers |
| MXPA02007903A MXPA02007903A (es) | 2000-02-15 | 2001-02-15 | Uso de acido 2-metil-tiazolidina-2, 4-dicarboxilico (2-mtdc) y/o sales fisiologicamente compatibles para tratar y/o prevenir canceres. |
| JP2001559441A JP2003522782A (ja) | 2000-02-15 | 2001-02-15 | ２−メチル−チアゾリジン−２，４−ジカルボン酸及び／又はその生理学的に許容できる塩の抗がん剤としての使用 |
| US11/117,569 US20050187271A1 (en) | 2000-02-15 | 2005-04-29 | Use of 2-methyl-thiazolidine-2,4-dicarboxylic acid and/or its physiologically tolerable salts as a cancer-fighting agent |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE10008159A DE10008159B4 (de) | 2000-02-15 | 2000-02-15 | Verwendung von 2-Methyl-thiazolidin-2,4-dicarbonsäure und/oder ihrer physiologisch verträglichen Salze als Antikrebsmittel |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE10008159A1 DE10008159A1 (de) | 2001-09-06 |
| DE10008159B4 true DE10008159B4 (de) | 2005-08-18 |
Family
ID=7631906
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE10008159A Expired - Fee Related DE10008159B4 (de) | 2000-02-15 | 2000-02-15 | Verwendung von 2-Methyl-thiazolidin-2,4-dicarbonsäure und/oder ihrer physiologisch verträglichen Salze als Antikrebsmittel |
| DE50100833T Expired - Lifetime DE50100833D1 (de) | 2000-02-15 | 2001-02-15 | Verwendung von 2-methyl-thiazolidin-2,4-dicarbonsäure und / oder ihrer physiologisch verträglichen salze zur herstellung eines medikaments zur behandlung von krebserkrankungen |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE50100833T Expired - Lifetime DE50100833D1 (de) | 2000-02-15 | 2001-02-15 | Verwendung von 2-methyl-thiazolidin-2,4-dicarbonsäure und / oder ihrer physiologisch verträglichen salze zur herstellung eines medikaments zur behandlung von krebserkrankungen |
Country Status (15)
| Country | Link |
|---|---|
| US (2) | US6943185B2 (enExample) |
| EP (1) | EP1255538B1 (enExample) |
| JP (1) | JP2003522782A (enExample) |
| CN (1) | CN1400899A (enExample) |
| AT (1) | ATE252383T1 (enExample) |
| AU (1) | AU783933B2 (enExample) |
| CA (1) | CA2399709C (enExample) |
| DE (2) | DE10008159B4 (enExample) |
| EA (1) | EA004592B1 (enExample) |
| ES (1) | ES2208571T3 (enExample) |
| MX (1) | MXPA02007903A (enExample) |
| PL (1) | PL357179A1 (enExample) |
| PT (1) | PT1255538E (enExample) |
| TR (1) | TR200302134T4 (enExample) |
| WO (1) | WO2001060343A2 (enExample) |
Families Citing this family (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20050197406A1 (en) * | 1999-04-14 | 2005-09-08 | Li Chiang J. | Method of treatment of lung cancer |
| DE10008159B4 (de) * | 2000-02-15 | 2005-08-18 | Rudy Dr. Susilo | Verwendung von 2-Methyl-thiazolidin-2,4-dicarbonsäure und/oder ihrer physiologisch verträglichen Salze als Antikrebsmittel |
| CN101838218A (zh) * | 2002-02-28 | 2010-09-22 | 日本烟草产业株式会社 | 酯化合物及其医药用途 |
| WO2005021486A1 (ja) * | 2003-08-29 | 2005-03-10 | Japan Tobacco Inc. | エステル誘導体及びその医薬用途 |
| DE102004021658A1 (de) * | 2004-05-03 | 2005-12-01 | Rudy Dr. Susilo | Kombinationspräparate enthaltend 2-Methylthiazolidin-2,4-dicarbonsäure |
| US20060030623A1 (en) * | 2004-07-16 | 2006-02-09 | Noboru Furukawa | Agent for the treatment or prevention of diabetes, obesity or arteriosclerosis |
| US8101774B2 (en) * | 2004-10-18 | 2012-01-24 | Japan Tobacco Inc. | Ester derivatives and medicinal use thereof |
| AU2005297923B2 (en) * | 2004-10-25 | 2010-12-23 | Japan Tobacco Inc. | Solid medicinal preparation improved in solubility and stability and process for producing the same |
| JP5439849B2 (ja) * | 2008-02-28 | 2014-03-12 | 味の素株式会社 | システイン誘導体 |
| JP5378713B2 (ja) * | 2008-06-19 | 2013-12-25 | 日本理化学薬品株式会社 | 外用組成物 |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE19711052A1 (de) * | 1997-03-03 | 1998-09-17 | Hans Prof Dr Rommelspacher | Verwendung von 2-Methyl-thiazolidin-2,4-dicarbonsäure als Mukolytikum |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE19711053C2 (de) * | 1997-03-03 | 1999-09-02 | Rommelspacher | Kombinationspräparat aus 2-Methyl-thiazolidin-2,4-dicarbonsäure und Paracetamol |
| DE10008159B4 (de) * | 2000-02-15 | 2005-08-18 | Rudy Dr. Susilo | Verwendung von 2-Methyl-thiazolidin-2,4-dicarbonsäure und/oder ihrer physiologisch verträglichen Salze als Antikrebsmittel |
-
2000
- 2000-02-15 DE DE10008159A patent/DE10008159B4/de not_active Expired - Fee Related
-
2001
- 2001-02-15 US US10/182,442 patent/US6943185B2/en not_active Expired - Fee Related
- 2001-02-15 CN CN01805095A patent/CN1400899A/zh active Pending
- 2001-02-15 ES ES01913699T patent/ES2208571T3/es not_active Expired - Lifetime
- 2001-02-15 TR TR2003/02134T patent/TR200302134T4/xx unknown
- 2001-02-15 AT AT01913699T patent/ATE252383T1/de not_active IP Right Cessation
- 2001-02-15 PT PT01913699T patent/PT1255538E/pt unknown
- 2001-02-15 PL PL01357179A patent/PL357179A1/xx not_active Application Discontinuation
- 2001-02-15 EP EP01913699A patent/EP1255538B1/de not_active Expired - Lifetime
- 2001-02-15 AU AU39190/01A patent/AU783933B2/en not_active Ceased
- 2001-02-15 EA EA200200853A patent/EA004592B1/ru not_active IP Right Cessation
- 2001-02-15 WO PCT/DE2001/000656 patent/WO2001060343A2/de not_active Ceased
- 2001-02-15 CA CA002399709A patent/CA2399709C/en not_active Expired - Fee Related
- 2001-02-15 MX MXPA02007903A patent/MXPA02007903A/es active IP Right Grant
- 2001-02-15 DE DE50100833T patent/DE50100833D1/de not_active Expired - Lifetime
- 2001-02-15 JP JP2001559441A patent/JP2003522782A/ja active Pending
-
2005
- 2005-04-29 US US11/117,569 patent/US20050187271A1/en not_active Abandoned
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE19711052A1 (de) * | 1997-03-03 | 1998-09-17 | Hans Prof Dr Rommelspacher | Verwendung von 2-Methyl-thiazolidin-2,4-dicarbonsäure als Mukolytikum |
Non-Patent Citations (1)
| Title |
|---|
| Derwent 1973-30093 U [21] * |
Also Published As
| Publication number | Publication date |
|---|---|
| ATE252383T1 (de) | 2003-11-15 |
| EP1255538A2 (de) | 2002-11-13 |
| AU783933B2 (en) | 2005-12-22 |
| PT1255538E (pt) | 2004-03-31 |
| EA004592B1 (ru) | 2004-06-24 |
| DE50100833D1 (de) | 2003-11-27 |
| DE10008159A1 (de) | 2001-09-06 |
| MXPA02007903A (es) | 2004-09-10 |
| EA200200853A1 (ru) | 2003-02-27 |
| US20050187271A1 (en) | 2005-08-25 |
| EP1255538B1 (de) | 2003-10-22 |
| CN1400899A (zh) | 2003-03-05 |
| PL357179A1 (en) | 2004-07-26 |
| WO2001060343A3 (de) | 2002-05-30 |
| TR200302134T4 (tr) | 2004-01-21 |
| ES2208571T3 (es) | 2004-06-16 |
| WO2001060343A2 (de) | 2001-08-23 |
| AU3919001A (en) | 2001-08-27 |
| US6943185B2 (en) | 2005-09-13 |
| US20030149085A1 (en) | 2003-08-07 |
| JP2003522782A (ja) | 2003-07-29 |
| CA2399709A1 (en) | 2001-08-23 |
| CA2399709C (en) | 2007-05-15 |
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