JPS6136493B2 - - Google Patents
Info
- Publication number
- JPS6136493B2 JPS6136493B2 JP53059759A JP5975978A JPS6136493B2 JP S6136493 B2 JPS6136493 B2 JP S6136493B2 JP 53059759 A JP53059759 A JP 53059759A JP 5975978 A JP5975978 A JP 5975978A JP S6136493 B2 JPS6136493 B2 JP S6136493B2
- Authority
- JP
- Japan
- Prior art keywords
- antitumor agent
- agent according
- present
- compound
- 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
- 239000002246 antineoplastic agent Substances 0.000 claims description 18
- -1 Nitrofurylvinyl Chemical group 0.000 claims description 9
- 201000001441 melanoma Diseases 0.000 claims description 9
- 208000005718 Stomach Neoplasms Diseases 0.000 claims description 6
- 206010017758 gastric cancer Diseases 0.000 claims description 6
- 201000011549 stomach cancer Diseases 0.000 claims description 6
- 239000008187 granular material Substances 0.000 claims description 4
- 239000000843 powder Substances 0.000 claims description 3
- 208000000461 Esophageal Neoplasms Diseases 0.000 claims description 2
- 206010030155 Oesophageal carcinoma Diseases 0.000 claims description 2
- 208000015634 Rectal Neoplasms Diseases 0.000 claims description 2
- 239000004480 active ingredient Substances 0.000 claims description 2
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 239000002775 capsule Substances 0.000 claims description 2
- 125000000392 cycloalkenyl group Chemical group 0.000 claims description 2
- 201000004101 esophageal cancer Diseases 0.000 claims description 2
- 239000002674 ointment Substances 0.000 claims description 2
- 206010038038 rectal cancer Diseases 0.000 claims description 2
- 201000001275 rectum cancer Diseases 0.000 claims description 2
- 239000003826 tablet Substances 0.000 claims description 2
- 208000002699 Digestive System Neoplasms Diseases 0.000 claims 2
- 125000000596 cyclohexenyl group Chemical group C1(=CCCCC1)* 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 description 35
- 206010028980 Neoplasm Diseases 0.000 description 13
- 241000700159 Rattus Species 0.000 description 12
- 239000000203 mixture Substances 0.000 description 11
- VZUNGTLZRAYYDE-UHFFFAOYSA-N N-methyl-N'-nitro-N-nitrosoguanidine Chemical compound O=NN(C)C(=N)N[N+]([O-])=O VZUNGTLZRAYYDE-UHFFFAOYSA-N 0.000 description 10
- 230000000694 effects Effects 0.000 description 10
- 210000004027 cell Anatomy 0.000 description 9
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 6
- GHASVSINZRGABV-UHFFFAOYSA-N Fluorouracil Chemical compound FC1=CNC(=O)NC1=O GHASVSINZRGABV-UHFFFAOYSA-N 0.000 description 6
- 230000000052 comparative effect Effects 0.000 description 6
- 229960002949 fluorouracil Drugs 0.000 description 6
- 241001465754 Metazoa Species 0.000 description 5
- 239000003814 drug Substances 0.000 description 5
- 238000009472 formulation Methods 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 4
- WZUVPPKBWHMQCE-UHFFFAOYSA-N Haematoxylin Chemical compound C12=CC(O)=C(O)C=C2CC2(O)C1C1=CC=C(O)C(O)=C1OC2 WZUVPPKBWHMQCE-UHFFFAOYSA-N 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- 231100000419 toxicity Toxicity 0.000 description 4
- 230000001988 toxicity Effects 0.000 description 4
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 3
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 3
- 229920002472 Starch Polymers 0.000 description 3
- 229940041181 antineoplastic drug Drugs 0.000 description 3
- 230000037396 body weight Effects 0.000 description 3
- 201000011510 cancer Diseases 0.000 description 3
- 229910002092 carbon dioxide Inorganic materials 0.000 description 3
- 239000001569 carbon dioxide Substances 0.000 description 3
- 238000012258 culturing Methods 0.000 description 3
- 239000003651 drinking water Substances 0.000 description 3
- 235000020188 drinking water Nutrition 0.000 description 3
- 229940079593 drug Drugs 0.000 description 3
- 235000021050 feed intake Nutrition 0.000 description 3
- 239000008101 lactose Substances 0.000 description 3
- 239000002609 medium Substances 0.000 description 3
- 238000000034 method Methods 0.000 description 3
- 238000012216 screening Methods 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 239000008107 starch Substances 0.000 description 3
- 235000019698 starch Nutrition 0.000 description 3
- 238000012360 testing method Methods 0.000 description 3
- 210000001519 tissue Anatomy 0.000 description 3
- 238000005303 weighing Methods 0.000 description 3
- UNPLRYRWJLTVAE-UHFFFAOYSA-N Cloperastine hydrochloride Chemical compound Cl.C1=CC(Cl)=CC=C1C(C=1C=CC=CC=1)OCCN1CCCCC1 UNPLRYRWJLTVAE-UHFFFAOYSA-N 0.000 description 2
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 2
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 2
- 241000699670 Mus sp. Species 0.000 description 2
- NWIBSHFKIJFRCO-WUDYKRTCSA-N Mytomycin Chemical compound C1N2C(C(C(C)=C(N)C3=O)=O)=C3[C@@H](COC(N)=O)[C@@]2(OC)[C@@H]2[C@H]1N2 NWIBSHFKIJFRCO-WUDYKRTCSA-N 0.000 description 2
- 150000001204 N-oxides Chemical class 0.000 description 2
- KFSLWBXXFJQRDL-UHFFFAOYSA-N Peracetic acid Chemical compound CC(=O)OO KFSLWBXXFJQRDL-UHFFFAOYSA-N 0.000 description 2
- 241000700157 Rattus norvegicus Species 0.000 description 2
- 229930006000 Sucrose Natural products 0.000 description 2
- 230000005856 abnormality Effects 0.000 description 2
- 239000008280 blood Substances 0.000 description 2
- 210000004369 blood Anatomy 0.000 description 2
- 238000009534 blood test Methods 0.000 description 2
- 238000009395 breeding Methods 0.000 description 2
- 230000001488 breeding effect Effects 0.000 description 2
- 235000014113 dietary fatty acids Nutrition 0.000 description 2
- 239000002270 dispersing agent Substances 0.000 description 2
- YQGOJNYOYNNSMM-UHFFFAOYSA-N eosin Chemical compound [Na+].OC(=O)C1=CC=CC=C1C1=C2C=C(Br)C(=O)C(Br)=C2OC2=C(Br)C(O)=C(Br)C=C21 YQGOJNYOYNNSMM-UHFFFAOYSA-N 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 229930195729 fatty acid Natural products 0.000 description 2
- 239000000194 fatty acid Substances 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 210000000056 organ Anatomy 0.000 description 2
- 239000012188 paraffin wax Substances 0.000 description 2
- 230000000144 pharmacologic effect Effects 0.000 description 2
- 230000035755 proliferation Effects 0.000 description 2
- 210000002235 sarcomere Anatomy 0.000 description 2
- 231100000456 subacute toxicity Toxicity 0.000 description 2
- 239000005720 sucrose Substances 0.000 description 2
- 229940124597 therapeutic agent Drugs 0.000 description 2
- 230000005748 tumor development Effects 0.000 description 2
- 210000002700 urine Anatomy 0.000 description 2
- IAVKWAIWFRXEGL-UHFFFAOYSA-N 2-[2-(5-nitrofuran-2-yl)ethenyl]-1,3-thiazole Chemical compound O1C([N+](=O)[O-])=CC=C1C=CC1=NC=CS1 IAVKWAIWFRXEGL-UHFFFAOYSA-N 0.000 description 1
- SXINBFXPADXIEY-UHFFFAOYSA-N 5-Nitrofurfural Chemical compound [O-][N+](=O)C1=CC=C(C=O)O1 SXINBFXPADXIEY-UHFFFAOYSA-N 0.000 description 1
- 206010005003 Bladder cancer Diseases 0.000 description 1
- 206010017993 Gastrointestinal neoplasms Diseases 0.000 description 1
- 241000282412 Homo Species 0.000 description 1
- 239000004166 Lanolin Substances 0.000 description 1
- 206010058467 Lung neoplasm malignant Diseases 0.000 description 1
- 241000699666 Mus <mouse, genus> Species 0.000 description 1
- 239000012980 RPMI-1640 medium Substances 0.000 description 1
- 208000006268 Sarcoma 180 Diseases 0.000 description 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 description 1
- 102000004142 Trypsin Human genes 0.000 description 1
- 108090000631 Trypsin Proteins 0.000 description 1
- 208000007097 Urinary Bladder Neoplasms Diseases 0.000 description 1
- 231100000215 acute (single dose) toxicity testing Toxicity 0.000 description 1
- 231100000403 acute toxicity Toxicity 0.000 description 1
- 230000007059 acute toxicity Effects 0.000 description 1
- 238000011047 acute toxicity test Methods 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 210000003484 anatomy Anatomy 0.000 description 1
- 230000000259 anti-tumor effect Effects 0.000 description 1
- 238000011888 autopsy Methods 0.000 description 1
- 235000014590 basal diet Nutrition 0.000 description 1
- 244000309466 calf Species 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000009535 clinical urine test Methods 0.000 description 1
- 230000002354 daily effect Effects 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 239000007884 disintegrant Substances 0.000 description 1
- 208000035475 disorder Diseases 0.000 description 1
- 230000009982 effect on human Effects 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 230000003203 everyday effect Effects 0.000 description 1
- 239000003925 fat Substances 0.000 description 1
- 239000010685 fatty oil Substances 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 235000011187 glycerol Nutrition 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 230000000571 inhibitory effect on melanoma Effects 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 229940039717 lanolin Drugs 0.000 description 1
- 235000019388 lanolin Nutrition 0.000 description 1
- 208000032839 leukemia Diseases 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 229940057995 liquid paraffin Drugs 0.000 description 1
- 230000007774 longterm Effects 0.000 description 1
- 231100000053 low toxicity Toxicity 0.000 description 1
- 201000005202 lung cancer Diseases 0.000 description 1
- 208000020816 lung neoplasm Diseases 0.000 description 1
- 230000014759 maintenance of location Effects 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 229960004857 mitomycin Drugs 0.000 description 1
- 231100000957 no side effect Toxicity 0.000 description 1
- 239000003883 ointment base Substances 0.000 description 1
- 230000007170 pathology Effects 0.000 description 1
- 230000035515 penetration Effects 0.000 description 1
- 235000019271 petrolatum Nutrition 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920000136 polysorbate Polymers 0.000 description 1
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 238000010298 pulverizing process Methods 0.000 description 1
- 238000001959 radiotherapy Methods 0.000 description 1
- 230000000384 rearing effect Effects 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 239000000523 sample Substances 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 210000002784 stomach Anatomy 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 238000001356 surgical procedure Methods 0.000 description 1
- 230000004083 survival effect Effects 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 238000002054 transplantation Methods 0.000 description 1
- 239000012588 trypsin Substances 0.000 description 1
- 210000004881 tumor cell Anatomy 0.000 description 1
- 238000002562 urinalysis Methods 0.000 description 1
- 201000005112 urinary bladder cancer Diseases 0.000 description 1
- 229940099259 vaseline Drugs 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 230000004584 weight gain Effects 0.000 description 1
- 235000019786 weight gain Nutrition 0.000 description 1
- 239000003871 white petrolatum Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Priority Applications (6)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP5975978A JPS54151134A (en) | 1978-05-19 | 1978-05-19 | Antitumorigenic agent |
| IT22723/79A IT1114243B (it) | 1978-05-19 | 1979-05-16 | Agente antitumorale a base di derivati tiazolici |
| CH454979A CH640850A5 (de) | 1978-05-19 | 1979-05-16 | Nitrofurylvinylthiazol-n-oxid-verbindungen als antitumormittel. |
| FR7912549A FR2426052A1 (fr) | 1978-05-19 | 1979-05-17 | Composes nitrofuryl-vinyleniques, nouveaux medicaments antitumoraux |
| DE2920247A DE2920247C2 (de) | 1978-05-19 | 1979-05-18 | Verwendung einer Nitrofuryl-vinylen-thiazol-N-oxid-Verbindung zur Herstellung von Antitumormitteln |
| GB7917473A GB2021111B (en) | 1978-05-19 | 1979-05-18 | Nitro - furyl - vinylene - thiazole n-oxides as antitumour agents |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP5975978A JPS54151134A (en) | 1978-05-19 | 1978-05-19 | Antitumorigenic agent |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS54151134A JPS54151134A (en) | 1979-11-28 |
| JPS6136493B2 true JPS6136493B2 (el) | 1986-08-19 |
Family
ID=13122504
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP5975978A Granted JPS54151134A (en) | 1978-05-19 | 1978-05-19 | Antitumorigenic agent |
Country Status (6)
| Country | Link |
|---|---|
| JP (1) | JPS54151134A (el) |
| CH (1) | CH640850A5 (el) |
| DE (1) | DE2920247C2 (el) |
| FR (1) | FR2426052A1 (el) |
| GB (1) | GB2021111B (el) |
| IT (1) | IT1114243B (el) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH0413498U (el) * | 1990-05-24 | 1992-02-03 | ||
| JPH0441034Y2 (el) * | 1986-04-23 | 1992-09-25 |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US8563592B2 (en) | 2001-11-01 | 2013-10-22 | Spectrum Pharmaceuticals, Inc. | Bladder cancer treatment and methods |
| DK1864660T3 (da) | 2001-11-01 | 2011-02-21 | Spectrum Pharmaceuticals Inc | Medicinske sammensætninger til intravesikal behandling af blærecancer |
| AU2007227692B2 (en) * | 2006-03-16 | 2012-09-13 | Women And Infants Hospital Of Rhode Island, Inc. | Nitrofuran compounds for the treatment of cancer and angiogenesis |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1545606A1 (de) * | 1965-07-29 | 1969-08-07 | Boehringer Mannheim Gmbh | Verfahren zur Herstellung neuer 5-Nitrofuran-Derivate |
| JPS5239033B1 (el) * | 1971-05-04 | 1977-10-03 | ||
| JPS5239033A (en) * | 1975-09-22 | 1977-03-26 | Meidensha Electric Mfg Co Ltd | An engine controlling device |
| GB2079568A (en) * | 1980-07-02 | 1982-01-20 | Hewlett Packard Co | Data compression apparatus and method |
| JPS5742662A (en) * | 1980-08-29 | 1982-03-10 | Chugai Pharmaceut Co Ltd | Benzoic acid amide derivative |
-
1978
- 1978-05-19 JP JP5975978A patent/JPS54151134A/ja active Granted
-
1979
- 1979-05-16 CH CH454979A patent/CH640850A5/de not_active IP Right Cessation
- 1979-05-16 IT IT22723/79A patent/IT1114243B/it active
- 1979-05-17 FR FR7912549A patent/FR2426052A1/fr active Granted
- 1979-05-18 DE DE2920247A patent/DE2920247C2/de not_active Expired
- 1979-05-18 GB GB7917473A patent/GB2021111B/en not_active Expired
Non-Patent Citations (1)
| Title |
|---|
| ARZNEIM.FORSCH=1967 * |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH0441034Y2 (el) * | 1986-04-23 | 1992-09-25 | ||
| JPH0413498U (el) * | 1990-05-24 | 1992-02-03 |
Also Published As
| Publication number | Publication date |
|---|---|
| FR2426052A1 (fr) | 1979-12-14 |
| GB2021111B (en) | 1982-11-03 |
| DE2920247C2 (de) | 1985-09-19 |
| IT1114243B (it) | 1986-01-27 |
| JPS54151134A (en) | 1979-11-28 |
| IT7922723A0 (it) | 1979-05-16 |
| GB2021111A (en) | 1979-11-28 |
| DE2920247A1 (de) | 1979-11-22 |
| CH640850A5 (de) | 1984-01-31 |
| FR2426052B1 (el) | 1983-04-08 |
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