US3635985A - 3-phenyl-4-acyloxycarbostyrils - Google Patents
3-phenyl-4-acyloxycarbostyrils Download PDFInfo
- Publication number
- US3635985A US3635985A US6316A US3635985DA US3635985A US 3635985 A US3635985 A US 3635985A US 6316 A US6316 A US 6316A US 3635985D A US3635985D A US 3635985DA US 3635985 A US3635985 A US 3635985A
- Authority
- US
- United States
- Prior art keywords
- phenyl
- acyloxycarbostyrils
- acetoxycarbostyril
- sec
- ethoxycarbonyloxycarbostyril
- 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 - Lifetime
Links
- -1 ETHOXY Chemical group 0.000 abstract description 15
- 230000000694 effects Effects 0.000 abstract description 5
- 231100000053 low toxicity Toxicity 0.000 abstract description 3
- WCYWZMWISLQXQU-UHFFFAOYSA-N methyl Chemical group [CH3] WCYWZMWISLQXQU-UHFFFAOYSA-N 0.000 abstract 1
- NIGOPJZDYZLKCV-UHFFFAOYSA-N CC(=O)OC1=C(C(=O)NC2=CC=CC=C12)C1=CC=CC=C1 Chemical compound CC(=O)OC1=C(C(=O)NC2=CC=CC=C12)C1=CC=CC=C1 NIGOPJZDYZLKCV-UHFFFAOYSA-N 0.000 description 9
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 8
- 241000699670 Mus sp. Species 0.000 description 7
- WNISVGSZMGXKHE-UHFFFAOYSA-N 4-hydroxy-3-phenyl-1h-quinolin-2-one Chemical compound OC=1NC2=CC=CC=C2C(=O)C=1C1=CC=CC=C1 WNISVGSZMGXKHE-UHFFFAOYSA-N 0.000 description 6
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- ANTSCNMPPGJYLG-UHFFFAOYSA-N chlordiazepoxide Chemical compound O=N=1CC(NC)=NC2=CC=C(Cl)C=C2C=1C1=CC=CC=C1 ANTSCNMPPGJYLG-UHFFFAOYSA-N 0.000 description 5
- 229960004782 chlordiazepoxide Drugs 0.000 description 5
- 150000001875 compounds Chemical class 0.000 description 5
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 4
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 2
- 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 2
- 229920002472 Starch Polymers 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 230000010933 acylation Effects 0.000 description 2
- 238000005917 acylation reaction Methods 0.000 description 2
- 229910052783 alkali metal Inorganic materials 0.000 description 2
- 150000001340 alkali metals Chemical class 0.000 description 2
- 239000002249 anxiolytic agent Substances 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 239000008101 lactose Substances 0.000 description 2
- 235000019359 magnesium stearate Nutrition 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 159000000000 sodium salts Chemical class 0.000 description 2
- 239000008107 starch Substances 0.000 description 2
- 235000019698 starch Nutrition 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- 238000005303 weighing Methods 0.000 description 2
- WJTBBDCZLGUDCJ-UHFFFAOYSA-N (2-oxo-3-phenyl-1H-quinolin-4-yl) benzoate Chemical compound O=C(OC1=C(C(=O)NC2=CC=CC=C12)C1=CC=CC=C1)C1=CC=CC=C1 WJTBBDCZLGUDCJ-UHFFFAOYSA-N 0.000 description 1
- NXLNNXIXOYSCMB-UHFFFAOYSA-N (4-nitrophenyl) carbonochloridate Chemical compound [O-][N+](=O)C1=CC=C(OC(Cl)=O)C=C1 NXLNNXIXOYSCMB-UHFFFAOYSA-N 0.000 description 1
- UVMBIUGTNDGJPV-UHFFFAOYSA-N 1-ethyl-4-hydroxy-3-phenylquinolin-2-one Chemical compound O=C1N(CC)C2=CC=CC=C2C(O)=C1C1=CC=CC=C1 UVMBIUGTNDGJPV-UHFFFAOYSA-N 0.000 description 1
- CLKIYIWKKBDFBS-UHFFFAOYSA-N 4-hydroxy-1-methyl-3-phenylquinolin-2-one Chemical compound O=C1N(C)C2=CC=CC=C2C(O)=C1C1=CC=CC=C1 CLKIYIWKKBDFBS-UHFFFAOYSA-N 0.000 description 1
- 244000215068 Acacia senegal Species 0.000 description 1
- 235000006491 Acacia senegal Nutrition 0.000 description 1
- 229920002134 Carboxymethyl cellulose Polymers 0.000 description 1
- 229920000084 Gum arabic Polymers 0.000 description 1
- 206010021118 Hypotonia Diseases 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
- 229920000168 Microcrystalline cellulose Polymers 0.000 description 1
- JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 description 1
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- ZMZDMBWJUHKJPS-UHFFFAOYSA-M Thiocyanate anion Chemical compound [S-]C#N ZMZDMBWJUHKJPS-UHFFFAOYSA-M 0.000 description 1
- 235000010489 acacia gum Nutrition 0.000 description 1
- 150000001242 acetic acid derivatives Chemical class 0.000 description 1
- WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 1
- 239000012346 acetyl chloride Substances 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000008065 acid anhydrides Chemical class 0.000 description 1
- 230000007059 acute toxicity Effects 0.000 description 1
- 231100000403 acute toxicity Toxicity 0.000 description 1
- 239000002671 adjuvant Substances 0.000 description 1
- 150000004703 alkoxides Chemical class 0.000 description 1
- 230000037396 body weight Effects 0.000 description 1
- 229910000019 calcium carbonate Inorganic materials 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- DKVNPHBNOWQYFE-UHFFFAOYSA-N carbamodithioic acid Chemical compound NC(S)=S DKVNPHBNOWQYFE-UHFFFAOYSA-N 0.000 description 1
- 239000001768 carboxy methyl cellulose Substances 0.000 description 1
- 235000010948 carboxy methyl cellulose Nutrition 0.000 description 1
- 239000008112 carboxymethyl-cellulose Substances 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 239000012990 dithiocarbamate Substances 0.000 description 1
- 239000002552 dosage form Substances 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- ZMZDMBWJUHKJPS-UHFFFAOYSA-N hydrogen thiocyanate Natural products SC#N ZMZDMBWJUHKJPS-UHFFFAOYSA-N 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 235000019813 microcrystalline cellulose Nutrition 0.000 description 1
- 239000008108 microcrystalline cellulose Substances 0.000 description 1
- 229940016286 microcrystalline cellulose Drugs 0.000 description 1
- CQDGTJPVBWZJAZ-UHFFFAOYSA-N monoethyl carbonate Chemical compound CCOC(O)=O CQDGTJPVBWZJAZ-UHFFFAOYSA-N 0.000 description 1
- 230000036640 muscle relaxation Effects 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
- 230000000638 stimulation Effects 0.000 description 1
- 208000011580 syndromic disease Diseases 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 235000012222 talc Nutrition 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 239000003204 tranquilizing agent Substances 0.000 description 1
- 230000002936 tranquilizing effect Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D215/20—Oxygen atoms
- C07D215/22—Oxygen atoms attached in position 2 or 4
Definitions
- R is methyl or ethoxy prepared by treating 3- phenyl-4-hydrocarbostyril with an acylating agent, which is useful as a minor tranquilizer with less side eifect and low toxicity.
- the present invention relates to 3-phenyl-4-acyloxycarbostyrils, and their production and use.
- the said 3-phenyl-4-acyloxycarbostyrils are representable by the formula:
- R is methyl or ethoxy and include specifically 3- phenyl-4-acetoxycarbostyril and 3 phenyl-4-ethoxycarbonyloxycarbostyril.
- 3-phenyl-4-acyloxycarbostyrils [I] exert a taming effect in fighting mice.
- mice of dd strain weighing 18 to 20 g. each were used and divided into 5 groups each consisting of a pair. Two mice were put on an electrical stimulator and a 200 ml. beaker was placed upside down over the mice. Electric stimulation was given at the intervals of 7 sec. (540 v., 3 ma.). The time until two mice began to fight was measured with a timer at various times after administration of the test compound and calculated in terms of the score of 1 to 9 respectively for 0 to 5 sec., 6 to 10 sec., 11 to 15 sec., 16 to 20 sec., 21 to 25 sec., 26 to 30 sec., 31 to 35 sec., 36 to 40 sec. and more than 40 sec. The dosage showing an average mark of 5 was taken as ED Results ED (mg/kg,
- Test compound per os) 3phenyl-4-acetoxycarbostyril 11.5 3-phenyl-4-ethoxycarbonyloxycarbostyril 10.5 3-phenyl-4-hydroxycarbostyril 100 3-phenyl-4-propionyloxycarbostyril 96.0 3-phenyl-4-phenacetyloxycarbostyril 100 3-phenyl-4-benzoyloxycarbostyril 100 3-phenyl-4-propoxycarbonyloxycarbostyril 96.0 3-phenyl-4-phenyloxycarbonyloxycarbostyril 100 1-ethyl-3-phenyl-4-acetoxycarbostyril 100 1-ethyl-3-phenyl-4-ethoxycarbonyloxycarbostyril 100 1-methyl-3-phenyl-4-hydroxycarbostyril 100 1-ethyl-3-phenyl-4-hydroxycarbostyril 100 chlordiazepoxide 18.0
- the 3-phenyl-4- acyloxycarbostyrils [I] are less effective in muscle relaxation, which is considered as an unfavorable side action for the use of tanquilizers.
- the ED values of 3-phenyl-4-acetoxycarbostyril and 3-phenyl-4-ethoxycarbonyloxycarbostyril are respectively 113.0 and 117.0 mg./kg. whereas the ED value of chlordiazepoxide is 45.3 mg./kg.
- the toxicity of the 3-phenyl- 4-acyloxycarbostyrils [I] is extremely low.
- the LD values of 3-phenyl-4-acetoxycarbostyril and 3-phenyl-4-ethoxycarbonyloxycarbostyril are both more than 3,000 mg./kg.
- the LD value of chlordiazepoxide is 1,325 mg./kg.
- 3-phenyl-4-acyloxycarbostyrils [I] of the present invention are useful as minor tranquilizers with less side effect and low toxicity.
- a clinical dosage of the 3-phenyl-4-acyloxycarbostyrils [I] depends on disease syndrome, body weight, age and administration mode, but it is generally in the range of 0.05 to 500 mg./day, preferably of 0.5 to 200 mg./day. They can be used in a unit dosage form as tablets or capsules for oral administration or optionally in combination with suitable adjuvants such as calcium carbonate, starch, lactose, talc, magnesium stearate, carboxymethyl cellulose and gum acacia. Further, they can be formulated into aqueous alcohol, glycol, oil solutions or oil-water emulsions for oral administration in the same manner as conventional medical substances are formulated.
- the 3-phenyllacyloxycarbostyril [I] is prepared by subjecting 3-phenyl- 4-hydroxycarbostyril of the formula:
- the acylation may be accomplished in one or two steps.
- the 3-phenyl-4-hydroxycarbostyril [II] or its monoalkali metal salt is treated with the reactive derivative of acetic acid or of carbonic acid ethyl ester in the presence or absence of a basic catalyst such as organic tertiary amine (e.g. pyridine, triethylamine, dimethylaniline) at a temperature from to 200 C., preferably from to 120 C.
- a basic catalyst such as organic tertiary amine (e.g. pyridine, triethylamine, dimethylaniline)
- the reactive derivative may be acid halide, acid anhydride, nitrophenyl ester, thiocyanate, dithiocarbamate, trithiophosphonate or the like.
- an inert organic solvent e.g. benzene, toluene, dioxane, carbon tetrachloride.
- the 3-phenyl-4-hydroxycarbostyril [II] or its monoalkali metal salt e.g. sodium salt, potassium salt
- phosgene or nitro-substituted phenoxycarbonyl chloride e.g. p-nitrophenoxycarbonyl chloride
- an inert organic solvent e.g. dichloromethane, chloroform, dioxane, tetrahydrofuran
- the above materials are mixed together, granulated and tableted in accordance with a conventional method to give 2,000 tablets, each weighing 50 mg.
- R is methyl or ethoxy
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Quinoline Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP749869 | 1969-02-01 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US3635985A true US3635985A (en) | 1972-01-18 |
Family
ID=11667424
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US6316A Expired - Lifetime US3635985A (en) | 1969-02-01 | 1970-01-27 | 3-phenyl-4-acyloxycarbostyrils |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US3635985A (enrdf_load_stackoverflow) |
| BE (1) | BE745289A (enrdf_load_stackoverflow) |
| CH (1) | CH529760A (enrdf_load_stackoverflow) |
| DE (1) | DE2003840A1 (enrdf_load_stackoverflow) |
| DK (1) | DK122127B (enrdf_load_stackoverflow) |
| FR (1) | FR2030240B1 (enrdf_load_stackoverflow) |
| GB (1) | GB1252861A (enrdf_load_stackoverflow) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3994900A (en) * | 1976-01-23 | 1976-11-30 | E. R. Squibb & Sons, Inc. | 6-(Or 8)-[[(substituted amino)alkyl]oxy(or thio)]-3,4-dihydro-4-phenyl-2(1H)-quinolinones |
| US4168312A (en) * | 1976-11-12 | 1979-09-18 | Merck Patent Gesellschaft Mit Beschrankter Haftung | Quinolone derivatives |
| US7579356B2 (en) | 2005-05-04 | 2009-08-25 | Janssen Pharmaceutica Nv | Thia-tetraazaacenaphthylene kinase inhibitors |
-
1970
- 1970-01-27 US US6316A patent/US3635985A/en not_active Expired - Lifetime
- 1970-01-28 DE DE19702003840 patent/DE2003840A1/de active Granted
- 1970-01-29 GB GB1252861D patent/GB1252861A/en not_active Expired
- 1970-01-30 DK DK44270AA patent/DK122127B/da unknown
- 1970-01-30 BE BE745289D patent/BE745289A/xx unknown
- 1970-01-30 FR FR707003333A patent/FR2030240B1/fr not_active Expired
- 1970-02-02 CH CH145370A patent/CH529760A/de not_active IP Right Cessation
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3994900A (en) * | 1976-01-23 | 1976-11-30 | E. R. Squibb & Sons, Inc. | 6-(Or 8)-[[(substituted amino)alkyl]oxy(or thio)]-3,4-dihydro-4-phenyl-2(1H)-quinolinones |
| US4168312A (en) * | 1976-11-12 | 1979-09-18 | Merck Patent Gesellschaft Mit Beschrankter Haftung | Quinolone derivatives |
| US7579356B2 (en) | 2005-05-04 | 2009-08-25 | Janssen Pharmaceutica Nv | Thia-tetraazaacenaphthylene kinase inhibitors |
Also Published As
| Publication number | Publication date |
|---|---|
| BE745289A (fr) | 1970-07-01 |
| FR2030240A1 (enrdf_load_stackoverflow) | 1970-11-13 |
| DE2003840A1 (de) | 1970-07-30 |
| GB1252861A (enrdf_load_stackoverflow) | 1971-11-10 |
| CH529760A (de) | 1972-10-31 |
| DK122127B (da) | 1972-01-24 |
| FR2030240B1 (enrdf_load_stackoverflow) | 1974-06-14 |
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