JPS6328045B2 - - Google Patents
Info
- Publication number
- JPS6328045B2 JPS6328045B2 JP54164950A JP16495079A JPS6328045B2 JP S6328045 B2 JPS6328045 B2 JP S6328045B2 JP 54164950 A JP54164950 A JP 54164950A JP 16495079 A JP16495079 A JP 16495079A JP S6328045 B2 JPS6328045 B2 JP S6328045B2
- Authority
- JP
- Japan
- Prior art keywords
- thiazolidine
- carboxylic acid
- cells
- therapeutic agent
- cancer
- 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
- DZLNHFMRPBPULJ-UHFFFAOYSA-N thioproline Chemical compound OC(=O)C1CSCN1 DZLNHFMRPBPULJ-UHFFFAOYSA-N 0.000 claims description 37
- 206010028980 Neoplasm Diseases 0.000 claims description 36
- 201000011510 cancer Diseases 0.000 claims description 25
- 239000003814 drug Substances 0.000 claims description 21
- 150000003839 salts Chemical class 0.000 claims description 20
- 229940124597 therapeutic agent Drugs 0.000 claims description 9
- 239000000243 solution Substances 0.000 claims description 7
- 239000008176 lyophilized powder Substances 0.000 claims description 6
- FBPFZTCFMRRESA-KVTDHHQDSA-N D-Mannitol Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KVTDHHQDSA-N 0.000 claims description 5
- 239000003795 chemical substances by application Substances 0.000 claims description 5
- 241000124008 Mammalia Species 0.000 claims description 4
- 238000004108 freeze drying Methods 0.000 claims description 4
- 230000012010 growth Effects 0.000 claims description 4
- 230000002401 inhibitory effect Effects 0.000 claims description 4
- 235000010355 mannitol Nutrition 0.000 claims description 4
- -1 alkali metal salt Chemical class 0.000 claims description 3
- 238000010255 intramuscular injection Methods 0.000 claims description 3
- 239000007927 intramuscular injection Substances 0.000 claims description 3
- 238000010253 intravenous injection Methods 0.000 claims description 3
- 239000004480 active ingredient Substances 0.000 claims description 2
- 229910052783 alkali metal Inorganic materials 0.000 claims description 2
- 229930195725 Mannitol Natural products 0.000 claims 1
- 239000000594 mannitol Substances 0.000 claims 1
- 230000001613 neoplastic effect Effects 0.000 claims 1
- 210000004027 cell Anatomy 0.000 description 35
- 229940079593 drug Drugs 0.000 description 14
- 238000011282 treatment Methods 0.000 description 13
- 230000030944 contact inhibition Effects 0.000 description 12
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- 210000004881 tumor cell Anatomy 0.000 description 9
- 238000000034 method Methods 0.000 description 7
- 241000282412 Homo Species 0.000 description 6
- 239000002246 antineoplastic agent Substances 0.000 description 6
- 229940127089 cytotoxic agent Drugs 0.000 description 6
- 230000001472 cytotoxic effect Effects 0.000 description 6
- 239000000126 substance Substances 0.000 description 6
- 231100000433 cytotoxic Toxicity 0.000 description 5
- 239000002609 medium Substances 0.000 description 5
- 238000006386 neutralization reaction Methods 0.000 description 5
- 231100000065 noncytotoxic Toxicity 0.000 description 5
- 230000002020 noncytotoxic effect Effects 0.000 description 5
- 201000008827 tuberculosis Diseases 0.000 description 5
- 230000004614 tumor growth Effects 0.000 description 5
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 4
- 230000037396 body weight Effects 0.000 description 4
- 239000002254 cytotoxic agent Substances 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 230000008569 process Effects 0.000 description 4
- 230000002441 reversible effect Effects 0.000 description 4
- 159000000000 sodium salts Chemical class 0.000 description 4
- 238000012360 testing method Methods 0.000 description 4
- 208000010507 Adenocarcinoma of Lung Diseases 0.000 description 3
- 206010027476 Metastases Diseases 0.000 description 3
- 229940041181 antineoplastic drug Drugs 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- 230000001086 cytosolic effect Effects 0.000 description 3
- 231100000599 cytotoxic agent Toxicity 0.000 description 3
- 201000010099 disease Diseases 0.000 description 3
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 3
- 238000002474 experimental method Methods 0.000 description 3
- 238000007918 intramuscular administration Methods 0.000 description 3
- 201000005249 lung adenocarcinoma Diseases 0.000 description 3
- 208000037841 lung tumor Diseases 0.000 description 3
- 231100000252 nontoxic Toxicity 0.000 description 3
- 230000003000 nontoxic effect Effects 0.000 description 3
- 230000009467 reduction Effects 0.000 description 3
- 238000011160 research Methods 0.000 description 3
- 230000009466 transformation Effects 0.000 description 3
- 238000011269 treatment regimen Methods 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- 206010006187 Breast cancer Diseases 0.000 description 2
- 208000026310 Breast neoplasm Diseases 0.000 description 2
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 description 2
- 206010027458 Metastases to lung Diseases 0.000 description 2
- 241000699666 Mus <mouse, genus> Species 0.000 description 2
- 241000699670 Mus sp. Species 0.000 description 2
- 206010033128 Ovarian cancer Diseases 0.000 description 2
- 206010061535 Ovarian neoplasm Diseases 0.000 description 2
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 2
- 206010061934 Salivary gland cancer Diseases 0.000 description 2
- 208000024770 Thyroid neoplasm Diseases 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 239000012830 cancer therapeutic Substances 0.000 description 2
- 210000000170 cell membrane Anatomy 0.000 description 2
- 238000002512 chemotherapy Methods 0.000 description 2
- 230000003013 cytotoxicity Effects 0.000 description 2
- 231100000135 cytotoxicity Toxicity 0.000 description 2
- 229960004279 formaldehyde Drugs 0.000 description 2
- 235000019256 formaldehyde Nutrition 0.000 description 2
- 238000009472 formulation Methods 0.000 description 2
- 239000004615 ingredient Substances 0.000 description 2
- 238000001990 intravenous administration Methods 0.000 description 2
- 210000004072 lung Anatomy 0.000 description 2
- 210000003632 microfilament Anatomy 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 229910052700 potassium Inorganic materials 0.000 description 2
- 239000011591 potassium Substances 0.000 description 2
- 238000011084 recovery Methods 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 206010041823 squamous cell carcinoma Diseases 0.000 description 2
- 230000006641 stabilisation Effects 0.000 description 2
- 238000011105 stabilization Methods 0.000 description 2
- 201000002510 thyroid cancer Diseases 0.000 description 2
- NOLHRFLIXVQPSZ-UHFFFAOYSA-N 1,3-thiazolidin-4-one Chemical compound O=C1CSCN1 NOLHRFLIXVQPSZ-UHFFFAOYSA-N 0.000 description 1
- 201000004384 Alopecia Diseases 0.000 description 1
- 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 1
- 241000282472 Canis lupus familiaris Species 0.000 description 1
- IVOMOUWHDPKRLL-KQYNXXCUSA-N Cyclic adenosine monophosphate Chemical compound C([C@H]1O2)OP(O)(=O)O[C@H]1[C@@H](O)[C@@H]2N1C(N=CN=C2N)=C2N=C1 IVOMOUWHDPKRLL-KQYNXXCUSA-N 0.000 description 1
- LEVWYRKDKASIDU-QWWZWVQMSA-N D-cystine Chemical compound OC(=O)[C@H](N)CSSC[C@@H](N)C(O)=O LEVWYRKDKASIDU-QWWZWVQMSA-N 0.000 description 1
- 239000006145 Eagle's minimal essential medium Substances 0.000 description 1
- GHASVSINZRGABV-UHFFFAOYSA-N Fluorouracil Chemical compound FC1=CNC(=O)NC1=O GHASVSINZRGABV-UHFFFAOYSA-N 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
- 239000004471 Glycine Substances 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- FBOZXECLQNJBKD-ZDUSSCGKSA-N L-methotrexate Chemical compound C=1N=C2N=C(N)N=C(N)C2=NC=1CN(C)C1=CC=C(C(=O)N[C@@H](CCC(O)=O)C(O)=O)C=C1 FBOZXECLQNJBKD-ZDUSSCGKSA-N 0.000 description 1
- 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 1
- 208000006552 Lewis Lung Carcinoma Diseases 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- 241000187479 Mycobacterium tuberculosis Species 0.000 description 1
- 206010063493 Premature ageing Diseases 0.000 description 1
- 208000032038 Premature aging Diseases 0.000 description 1
- 241000700159 Rattus Species 0.000 description 1
- 208000004337 Salivary Gland Neoplasms Diseases 0.000 description 1
- 208000008312 Tooth Loss Diseases 0.000 description 1
- IVOMOUWHDPKRLL-UHFFFAOYSA-N UNPD107823 Natural products O1C2COP(O)(=O)OC2C(O)C1N1C(N=CN=C2N)=C2N=C1 IVOMOUWHDPKRLL-UHFFFAOYSA-N 0.000 description 1
- 241000700605 Viruses Species 0.000 description 1
- 206010047700 Vomiting Diseases 0.000 description 1
- CJGYSWNGNKCJSB-YVLZZHOMSA-M [(4ar,6r,7r,7ar)-6-[6-(butanoylamino)purin-9-yl]-2-oxido-2-oxo-4a,6,7,7a-tetrahydro-4h-furo[3,2-d][1,3,2]dioxaphosphinin-7-yl] butanoate Chemical compound C([C@H]1O2)OP([O-])(=O)O[C@H]1[C@@H](OC(=O)CCC)[C@@H]2N1C(N=CN=C2NC(=O)CCC)=C2N=C1 CJGYSWNGNKCJSB-YVLZZHOMSA-M 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 1
- 150000001342 alkaline earth metals Chemical class 0.000 description 1
- 150000001413 amino acids Chemical class 0.000 description 1
- 230000000202 analgesic effect Effects 0.000 description 1
- 230000000259 anti-tumor effect Effects 0.000 description 1
- 238000011394 anticancer treatment Methods 0.000 description 1
- 239000003972 antineoplastic antibiotic Substances 0.000 description 1
- 239000012736 aqueous medium Substances 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- 244000309466 calf Species 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 239000003183 carcinogenic agent Substances 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
- 230000032823 cell division Effects 0.000 description 1
- 230000003915 cell function Effects 0.000 description 1
- 230000010261 cell growth Effects 0.000 description 1
- 230000009087 cell motility Effects 0.000 description 1
- 210000003855 cell nucleus Anatomy 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 229940095074 cyclic amp Drugs 0.000 description 1
- 229960003067 cystine Drugs 0.000 description 1
- 230000003436 cytoskeletal effect Effects 0.000 description 1
- 238000011393 cytotoxic chemotherapy Methods 0.000 description 1
- 229940000033 dermatological agent Drugs 0.000 description 1
- 239000003241 dermatological agent Substances 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 229960002949 fluorouracil Drugs 0.000 description 1
- 239000008103 glucose Substances 0.000 description 1
- 230000036433 growing body Effects 0.000 description 1
- 208000024963 hair loss Diseases 0.000 description 1
- 230000003676 hair loss Effects 0.000 description 1
- 201000003911 head and neck carcinoma Diseases 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 230000000977 initiatory effect Effects 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 230000003834 intracellular effect Effects 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 208000032839 leukemia Diseases 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 159000000003 magnesium salts Chemical class 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 230000009401 metastasis Effects 0.000 description 1
- 230000001394 metastastic effect Effects 0.000 description 1
- 208000037819 metastatic cancer Diseases 0.000 description 1
- 208000011575 metastatic malignant neoplasm Diseases 0.000 description 1
- 206010061289 metastatic neoplasm Diseases 0.000 description 1
- 229960000485 methotrexate Drugs 0.000 description 1
- 150000004712 monophosphates Chemical class 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 230000003472 neutralizing effect Effects 0.000 description 1
- 231100000956 nontoxicity Toxicity 0.000 description 1
- 230000001151 other effect Effects 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 239000006187 pill Substances 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Substances [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 1
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 1
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
- 239000011148 porous material Substances 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 230000002250 progressing effect Effects 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 201000003804 salivary gland carcinoma Diseases 0.000 description 1
- 230000037390 scarring Effects 0.000 description 1
- 208000011581 secondary neoplasm Diseases 0.000 description 1
- 210000002966 serum Anatomy 0.000 description 1
- YWLXEQKAKDKVBQ-UHFFFAOYSA-M sodium;1,3-thiazolidine-4-carboxylate Chemical compound [Na+].[O-]C(=O)C1CSCN1 YWLXEQKAKDKVBQ-UHFFFAOYSA-M 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 230000004083 survival effect Effects 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 210000001519 tissue Anatomy 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 230000004565 tumor cell growth Effects 0.000 description 1
- 208000025421 tumor of uterus Diseases 0.000 description 1
- 206010046766 uterine cancer Diseases 0.000 description 1
- 239000011782 vitamin Substances 0.000 description 1
- 229940088594 vitamin Drugs 0.000 description 1
- 229930003231 vitamin Natural products 0.000 description 1
- 235000013343 vitamin Nutrition 0.000 description 1
- 230000008673 vomiting Effects 0.000 description 1
- 230000003442 weekly effect Effects 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
-
- 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
- A61K9/14—Particulate form, e.g. powders, Processes for size reducing of pure drugs or the resulting products, Pure drug nanoparticles
- A61K9/19—Particulate form, e.g. powders, Processes for size reducing of pure drugs or the resulting products, Pure drug nanoparticles lyophilised, i.e. freeze-dried, solutions or dispersions
-
- 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)
- Veterinary Medicine (AREA)
- Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- General Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Public Health (AREA)
- Epidemiology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Thiazole And Isothizaole Compounds (AREA)
- Medicinal Preparation (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US05/971,729 US4384001A (en) | 1978-12-21 | 1978-12-21 | Treatment of tumors with thiazolidine-4-carboxylic acid |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS55115822A JPS55115822A (en) | 1980-09-06 |
| JPS6328045B2 true JPS6328045B2 (en, 2012) | 1988-06-07 |
Family
ID=25518727
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP16495079A Granted JPS55115822A (en) | 1978-12-21 | 1979-12-20 | Tumor treating agent and its manufacture |
Country Status (16)
| Country | Link |
|---|---|
| US (1) | US4384001A (en, 2012) |
| JP (1) | JPS55115822A (en, 2012) |
| AU (1) | AU5390579A (en, 2012) |
| BE (1) | BE880744A (en, 2012) |
| CA (1) | CA1149284A (en, 2012) |
| DE (1) | DE2951050A1 (en, 2012) |
| DK (1) | DK542979A (en, 2012) |
| ES (1) | ES8102108A1 (en, 2012) |
| FR (1) | FR2444459A1 (en, 2012) |
| GB (1) | GB2039736B (en, 2012) |
| IL (1) | IL58948A0 (en, 2012) |
| IT (1) | IT1193348B (en, 2012) |
| LU (1) | LU82013A1 (en, 2012) |
| NL (1) | NL7909199A (en, 2012) |
| SE (1) | SE7910300L (en, 2012) |
| ZA (1) | ZA796918B (en, 2012) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH01170063U (en, 2012) * | 1988-05-11 | 1989-11-30 | ||
| JPH0467539U (en, 2012) * | 1990-10-18 | 1992-06-16 |
Families Citing this family (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IE53332B1 (en) * | 1980-03-14 | 1988-10-26 | Efamol Ltd | Pharmaceutical compositions |
| JPS57128625A (en) * | 1981-01-30 | 1982-08-10 | Rikagaku Kenkyusho | Carcinostatic |
| US4335210A (en) * | 1981-02-11 | 1982-06-15 | Cornell Research Foundation | Method of producing L-cysteine |
| FR2547728B1 (fr) * | 1983-06-24 | 1986-05-02 | Riker Laboratories Inc | Medicament a base d'acide d thiazolidine carboxylique |
| FR2547729B1 (fr) * | 1983-06-24 | 1986-05-02 | Riker Laboratories Inc | Medicament a base d'acide dl thiazolidine carboxylique |
| JPS62501769A (ja) * | 1984-12-18 | 1987-07-16 | デイビツト ラビン | 細胞毒性アルデヒドとベニシラミンとの反応性成物を含有する抗腫瘍組成物及びその使用方法 |
| JPH066578B2 (ja) * | 1985-12-27 | 1994-01-26 | 三共株式会社 | チアゾリジン誘導体 |
| DE69214467T3 (de) * | 1991-01-10 | 2000-09-28 | Transcend Therapeutics, Inc. | Verwendung von L-2-oxo Thiazolidin-4-carboxylat zur Behandlung von Atemnotsyndrom |
| ATE209645T1 (de) * | 1994-06-14 | 2001-12-15 | Dainippon Pharmaceutical Co | Neue verbindung, verfahren zu ihrer herstellung und antitumormittel |
| ES2277787B1 (es) * | 2006-01-02 | 2008-06-16 | Universidad De Cadiz | Empleo de tioprolina en tratamientos de reduccion de peso corporal. |
-
1978
- 1978-12-21 US US05/971,729 patent/US4384001A/en not_active Expired - Lifetime
-
1979
- 1979-12-12 GB GB7942753A patent/GB2039736B/en not_active Expired
- 1979-12-13 IL IL58948A patent/IL58948A0/xx unknown
- 1979-12-14 SE SE7910300A patent/SE7910300L/xx unknown
- 1979-12-17 AU AU53905/79A patent/AU5390579A/en not_active Abandoned
- 1979-12-18 IT IT28170/79A patent/IT1193348B/it active
- 1979-12-19 ES ES487052A patent/ES8102108A1/es not_active Expired
- 1979-12-19 CA CA000342263A patent/CA1149284A/en not_active Expired
- 1979-12-19 DK DK542979A patent/DK542979A/da unknown
- 1979-12-19 DE DE19792951050 patent/DE2951050A1/de not_active Withdrawn
- 1979-12-19 FR FR7931158A patent/FR2444459A1/fr active Granted
- 1979-12-19 BE BE0/198657A patent/BE880744A/fr not_active IP Right Cessation
- 1979-12-19 LU LU82013A patent/LU82013A1/fr unknown
- 1979-12-20 NL NL7909199A patent/NL7909199A/nl not_active Application Discontinuation
- 1979-12-20 JP JP16495079A patent/JPS55115822A/ja active Granted
- 1979-12-20 ZA ZA00796918A patent/ZA796918B/xx unknown
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH01170063U (en, 2012) * | 1988-05-11 | 1989-11-30 | ||
| JPH0467539U (en, 2012) * | 1990-10-18 | 1992-06-16 |
Also Published As
| Publication number | Publication date |
|---|---|
| US4384001A (en) | 1983-05-17 |
| DK542979A (da) | 1980-06-22 |
| ES487052A0 (es) | 1980-12-16 |
| FR2444459A1 (fr) | 1980-07-18 |
| CA1149284A (en) | 1983-07-05 |
| IT7928170A0 (it) | 1979-12-18 |
| NL7909199A (nl) | 1980-06-24 |
| IT1193348B (it) | 1988-06-15 |
| GB2039736B (en) | 1983-04-13 |
| BE880744A (fr) | 1980-06-19 |
| DE2951050A1 (de) | 1980-07-10 |
| AU5390579A (en) | 1980-06-26 |
| IL58948A0 (en) | 1980-03-31 |
| GB2039736A (en) | 1980-08-20 |
| ES8102108A1 (es) | 1980-12-16 |
| JPS55115822A (en) | 1980-09-06 |
| LU82013A1 (fr) | 1981-02-03 |
| FR2444459B1 (en, 2012) | 1983-04-01 |
| SE7910300L (sv) | 1980-06-22 |
| ZA796918B (en) | 1980-11-26 |
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