JPS6041655A - 尿素類およびチオ尿素類、それらの製造法並びに医薬用途 - Google Patents
尿素類およびチオ尿素類、それらの製造法並びに医薬用途Info
- Publication number
- JPS6041655A JPS6041655A JP59147751A JP14775184A JPS6041655A JP S6041655 A JPS6041655 A JP S6041655A JP 59147751 A JP59147751 A JP 59147751A JP 14775184 A JP14775184 A JP 14775184A JP S6041655 A JPS6041655 A JP S6041655A
- Authority
- JP
- Japan
- Prior art keywords
- chloro
- formula
- urea
- dimethylphenyl
- phenylcomethyl
- 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
- 238000004519 manufacturing process Methods 0.000 title claims description 5
- 235000013877 carbamide Nutrition 0.000 title description 17
- 150000003672 ureas Chemical class 0.000 title description 12
- 150000003585 thioureas Chemical class 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims description 38
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 12
- -1 4-chloro-2-methylphenyl Chemical group 0.000 claims description 11
- 241000124008 Mammalia Species 0.000 claims description 9
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 8
- 239000001257 hydrogen Substances 0.000 claims description 8
- 229910052739 hydrogen Inorganic materials 0.000 claims description 8
- 239000004202 carbamide Substances 0.000 claims description 7
- 239000008194 pharmaceutical composition Substances 0.000 claims description 7
- 125000000217 alkyl group Chemical group 0.000 claims description 6
- 201000001320 Atherosclerosis Diseases 0.000 claims description 4
- 239000003937 drug carrier Substances 0.000 claims description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 4
- 125000003545 alkoxy group Chemical group 0.000 claims description 3
- 230000003143 atherosclerotic effect Effects 0.000 claims description 3
- 230000003902 lesion Effects 0.000 claims description 3
- 208000031226 Hyperlipidaemia Diseases 0.000 claims description 2
- 125000004414 alkyl thio group Chemical group 0.000 claims description 2
- 230000001629 suppression Effects 0.000 claims description 2
- 231100000252 nontoxic Toxicity 0.000 claims 3
- 230000003000 nontoxic effect Effects 0.000 claims 3
- 150000001840 cholesterol esters Chemical class 0.000 claims 2
- 125000000467 secondary amino group Chemical class [H]N([*:1])[*:2] 0.000 claims 2
- 125000001475 halogen functional group Chemical group 0.000 claims 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 1
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 33
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 27
- 239000000243 solution Substances 0.000 description 19
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 18
- 239000000203 mixture Substances 0.000 description 17
- 239000007787 solid Substances 0.000 description 15
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 12
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 10
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
- 239000007788 liquid Substances 0.000 description 8
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- 238000000034 method Methods 0.000 description 7
- 239000003921 oil Substances 0.000 description 7
- 235000019198 oils Nutrition 0.000 description 7
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 6
- HVYWMOMLDIMFJA-DPAQBDIFSA-N cholesterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2 HVYWMOMLDIMFJA-DPAQBDIFSA-N 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 5
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 5
- 229910052753 mercury Inorganic materials 0.000 description 5
- 239000012044 organic layer Substances 0.000 description 5
- AHWALFGBDFAJAI-UHFFFAOYSA-N phenyl carbonochloridate Chemical compound ClC(=O)OC1=CC=CC=C1 AHWALFGBDFAJAI-UHFFFAOYSA-N 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 description 4
- 238000009835 boiling Methods 0.000 description 4
- 239000012267 brine Substances 0.000 description 4
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- 239000000047 product Substances 0.000 description 4
- 150000003335 secondary amines Chemical class 0.000 description 4
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- 239000000725 suspension Substances 0.000 description 4
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
- 238000000023 Kugelrohr distillation Methods 0.000 description 3
- 241000699670 Mus sp. Species 0.000 description 3
- 229930182558 Sterol Natural products 0.000 description 3
- 102000001494 Sterol O-Acyltransferase Human genes 0.000 description 3
- 108010054082 Sterol O-acyltransferase Proteins 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 239000004480 active ingredient Substances 0.000 description 3
- 239000000010 aprotic solvent Substances 0.000 description 3
- 235000012000 cholesterol Nutrition 0.000 description 3
- 239000000706 filtrate Substances 0.000 description 3
- 239000007789 gas Substances 0.000 description 3
- 239000013067 intermediate product Substances 0.000 description 3
- 210000004185 liver Anatomy 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 210000002966 serum Anatomy 0.000 description 3
- 235000003702 sterols Nutrition 0.000 description 3
- 150000003432 sterols Chemical class 0.000 description 3
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 2
- 102000004190 Enzymes Human genes 0.000 description 2
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- 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 2
- JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 description 2
- 241000700159 Rattus Species 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 238000010521 absorption reaction Methods 0.000 description 2
- 210000004100 adrenal gland Anatomy 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 230000000879 anti-atherosclerotic effect Effects 0.000 description 2
- 239000002775 capsule Substances 0.000 description 2
- 239000000969 carrier Substances 0.000 description 2
- 230000001906 cholesterol absorption Effects 0.000 description 2
- 235000005911 diet Nutrition 0.000 description 2
- 230000037213 diet Effects 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- 150000002185 fatty acyl-CoAs Chemical class 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 239000008187 granular material Substances 0.000 description 2
- 230000005484 gravity Effects 0.000 description 2
- 230000002401 inhibitory effect Effects 0.000 description 2
- 239000000543 intermediate Substances 0.000 description 2
- 239000010410 layer Substances 0.000 description 2
- 150000002632 lipids Chemical class 0.000 description 2
- RLMPWGAJKNLQIO-UHFFFAOYSA-N n-[[4-(2,2-dimethylpropyl)phenyl]methyl]heptan-1-amine Chemical compound CCCCCCCNCC1=CC=C(CC(C)(C)C)C=C1 RLMPWGAJKNLQIO-UHFFFAOYSA-N 0.000 description 2
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- UKTDAQDTJFLOMR-UHFFFAOYSA-N phenyl n-(4-chloro-2,6-dimethylphenyl)carbamate Chemical compound CC1=CC(Cl)=CC(C)=C1NC(=O)OC1=CC=CC=C1 UKTDAQDTJFLOMR-UHFFFAOYSA-N 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 239000003755 preservative agent Substances 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 239000003826 tablet Substances 0.000 description 2
- 238000004809 thin layer chromatography Methods 0.000 description 2
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 2
- MHTIYKGRFKCWAU-UHFFFAOYSA-N (4-chloro-2,6-dimethylphenyl)azanium;chloride Chemical compound Cl.CC1=CC(Cl)=CC(C)=C1N MHTIYKGRFKCWAU-UHFFFAOYSA-N 0.000 description 1
- HNENEALJPWJWJY-UHFFFAOYSA-N 2,4-difluoro-1-isocyanatobenzene Chemical compound FC1=CC=C(N=C=O)C(F)=C1 HNENEALJPWJWJY-UHFFFAOYSA-N 0.000 description 1
- UFFBMTHBGFGIHF-UHFFFAOYSA-N 2,6-dimethylaniline Chemical compound CC1=CC=CC(C)=C1N UFFBMTHBGFGIHF-UHFFFAOYSA-N 0.000 description 1
- RYJIUCWUVTUWGF-UHFFFAOYSA-N 4-(2,2-dimethylpropyl)-n-heptylbenzamide Chemical compound CCCCCCCNC(=O)C1=CC=C(CC(C)(C)C)C=C1 RYJIUCWUVTUWGF-UHFFFAOYSA-N 0.000 description 1
- XSNKOUWZXGZYPF-UHFFFAOYSA-N 4-(2,2-dimethylpropyl)benzoic acid Chemical compound CC(C)(C)CC1=CC=C(C(O)=O)C=C1 XSNKOUWZXGZYPF-UHFFFAOYSA-N 0.000 description 1
- XEGGPWMGBNKOQH-UHFFFAOYSA-N 4-(2,2-dimethylpropyl)benzoyl chloride Chemical compound CC(C)(C)CC1=CC=C(C(Cl)=O)C=C1 XEGGPWMGBNKOQH-UHFFFAOYSA-N 0.000 description 1
- JCLZLZKUISPXDC-UHFFFAOYSA-N 4-chloro-2,6-dimethylaniline Chemical compound CC1=CC(Cl)=CC(C)=C1N JCLZLZKUISPXDC-UHFFFAOYSA-N 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
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- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 description 1
- KXDHJXZQYSOELW-UHFFFAOYSA-N Carbamic acid Chemical class NC(O)=O KXDHJXZQYSOELW-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 235000019739 Dicalciumphosphate Nutrition 0.000 description 1
- 241000233866 Fungi Species 0.000 description 1
- 102100034472 H(+)/Cl(-) exchange transporter 4 Human genes 0.000 description 1
- WJYIASZWHGOTOU-UHFFFAOYSA-N Heptylamine Chemical compound CCCCCCCN WJYIASZWHGOTOU-UHFFFAOYSA-N 0.000 description 1
- 101000710229 Homo sapiens H(+)/Cl(-) exchange transporter 4 Proteins 0.000 description 1
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- 235000013343 vitamin Nutrition 0.000 description 1
- 150000003722 vitamin derivatives Chemical class 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C275/00—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups
- C07C275/28—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of urea groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
- C07C275/30—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of urea groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton being further substituted by halogen atoms, or by nitro or nitroso groups
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/06—Antihyperlipidemics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Obesity (AREA)
- Diabetes (AREA)
- Hematology (AREA)
- Urology & Nephrology (AREA)
- Vascular Medicine (AREA)
- Cardiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US51532183A | 1983-07-19 | 1983-07-19 | |
| US515321 | 1983-07-19 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS6041655A true JPS6041655A (ja) | 1985-03-05 |
| JPH0585543B2 JPH0585543B2 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1993-12-07 |
Family
ID=24050874
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP59147751A Granted JPS6041655A (ja) | 1983-07-19 | 1984-07-18 | 尿素類およびチオ尿素類、それらの製造法並びに医薬用途 |
Country Status (7)
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5646881A (en) * | 1979-09-13 | 1981-04-28 | Firmenich & Cie | Manufacture of muscone* novel pyran derivative* its manufacture and manufacture of unsaturated macrocyclic ketone |
| US5397781A (en) * | 1992-03-18 | 1995-03-14 | Mochida Pharmaceutical Company, Limited | Pyrimidine derivatives |
| US5416212A (en) * | 1991-12-25 | 1995-05-16 | Taisho Pharmaceutical Co., Ltd. | Anilide derivatives |
| US5475130A (en) * | 1990-11-26 | 1995-12-12 | Taisho Pharmaceutical Co., Ltd. | Anilide derivative |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5003106A (en) * | 1983-07-19 | 1991-03-26 | American Cyanamid Company | Antiatherosclerotic ureas and thioureas |
| US5032608A (en) * | 1986-09-10 | 1991-07-16 | Dudrick Stanley J | Method and substrate composition for treating atherosclerosis |
| US5248688A (en) * | 1986-09-10 | 1993-09-28 | Dudrick Medical Research Fund I, Ltd. | Method and substrate composition for treating atherosclerosis |
| US4994465A (en) * | 1989-02-17 | 1991-02-19 | Warner-Lambert Company | Antihyperlipidemic and antiatherosclerotic trisubstituted urea compounds |
| GB9020841D0 (en) * | 1990-09-25 | 1990-11-07 | Wellcome Found | Anti-atherosclerotic aryl compounds |
| US5420164A (en) * | 1991-04-04 | 1995-05-30 | Yoshitomi Pharmaceutical Industries, Ltd. | Cycloalkylurea compounds |
| US5378728A (en) * | 1992-11-03 | 1995-01-03 | Sandoz Ltd. | Benzoic acid derivatives as antidiabetic agents |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5224104B2 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) * | 1974-10-07 | 1977-06-29 | ||
| JPS5461149A (en) * | 1977-10-20 | 1979-05-17 | Kumiai Chem Ind Co Ltd | 3-chloro-4-fluorophenyl urea derivative, its preparation and herbicide containing the same |
| US4387106A (en) * | 1982-01-26 | 1983-06-07 | American Cyanamid Company | Method of treating atherosclerosis with di(aralkyl)ureas and di(aralkyl)thioureas |
| US4387105A (en) * | 1982-01-26 | 1983-06-07 | American Cyanamid Company | Methods of treating atherosclerosis with dialkylureas and dialkylthioureas |
| IL67417A (en) * | 1982-01-26 | 1989-10-31 | American Cyanamid Co | Antiatherosclerotic substituted ureas,process for their preparation and pharmaceutical compositions containing them |
-
1984
- 1984-07-05 GB GB08417126A patent/GB2149394B/en not_active Expired
- 1984-07-17 AT AT0231284A patent/AT394191B/de not_active IP Right Cessation
- 1984-07-17 CA CA000459032A patent/CA1239150A/en not_active Expired
- 1984-07-18 NL NL8402272A patent/NL8402272A/nl not_active Application Discontinuation
- 1984-07-18 BE BE0/213345A patent/BE900178A/fr not_active IP Right Cessation
- 1984-07-18 JP JP59147751A patent/JPS6041655A/ja active Granted
- 1984-07-19 FR FR8411471A patent/FR2549473B1/fr not_active Expired
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5646881A (en) * | 1979-09-13 | 1981-04-28 | Firmenich & Cie | Manufacture of muscone* novel pyran derivative* its manufacture and manufacture of unsaturated macrocyclic ketone |
| US5475130A (en) * | 1990-11-26 | 1995-12-12 | Taisho Pharmaceutical Co., Ltd. | Anilide derivative |
| US5416212A (en) * | 1991-12-25 | 1995-05-16 | Taisho Pharmaceutical Co., Ltd. | Anilide derivatives |
| US5397781A (en) * | 1992-03-18 | 1995-03-14 | Mochida Pharmaceutical Company, Limited | Pyrimidine derivatives |
Also Published As
| Publication number | Publication date |
|---|---|
| NL8402272A (nl) | 1985-02-18 |
| FR2549473A1 (fr) | 1985-01-25 |
| BE900178A (fr) | 1985-01-18 |
| GB8417126D0 (en) | 1984-08-08 |
| GB2149394B (en) | 1986-09-24 |
| CA1239150A (en) | 1988-07-12 |
| GB2149394A (en) | 1985-06-12 |
| JPH0585543B2 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1993-12-07 |
| AT394191B (de) | 1992-02-10 |
| FR2549473B1 (fr) | 1988-07-22 |
| ATA231284A (de) | 1991-08-15 |
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