NO115333B - - Google Patents
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- Publication number
- NO115333B NO115333B NO154170A NO15417064A NO115333B NO 115333 B NO115333 B NO 115333B NO 154170 A NO154170 A NO 154170A NO 15417064 A NO15417064 A NO 15417064A NO 115333 B NO115333 B NO 115333B
- Authority
- NO
- Norway
- Prior art keywords
- methyl
- chloro
- acid
- phenoxyacetate
- mixture
- Prior art date
Links
- -1 methyl-3-chloro-4-(1-chloromethylpropyl-sulfonyl)-phenoxyacetate Chemical compound 0.000 claims description 41
- 238000000034 method Methods 0.000 claims description 35
- 150000001875 compounds Chemical class 0.000 claims description 22
- 150000002148 esters Chemical class 0.000 claims description 11
- 238000002360 preparation method Methods 0.000 claims description 11
- 239000002253 acid Substances 0.000 claims description 7
- 125000000217 alkyl group Chemical group 0.000 claims description 6
- 150000003839 salts Chemical class 0.000 claims description 6
- 150000001408 amides Chemical class 0.000 claims description 5
- 229910052739 hydrogen Inorganic materials 0.000 claims description 5
- 239000001257 hydrogen Substances 0.000 claims description 5
- 239000007858 starting material Substances 0.000 claims description 5
- 125000000717 hydrazino group Chemical group [H]N([*])N([H])[H] 0.000 claims description 4
- 229910052736 halogen Inorganic materials 0.000 claims description 2
- 150000002367 halogens Chemical class 0.000 claims description 2
- 150000002431 hydrogen Chemical class 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 150000002429 hydrazines Chemical class 0.000 claims 1
- 239000000047 product Substances 0.000 description 23
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 20
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
- 239000000203 mixture Substances 0.000 description 16
- 239000000243 solution Substances 0.000 description 16
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 14
- 238000006243 chemical reaction Methods 0.000 description 14
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 13
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 12
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 12
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- 239000003153 chemical reaction reagent Substances 0.000 description 9
- 239000000376 reactant Substances 0.000 description 9
- 239000007787 solid Substances 0.000 description 9
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 8
- PSEULCJHKNCOIU-UHFFFAOYSA-N ethyl 2-(4-amino-3-chlorophenoxy)acetate Chemical compound CCOC(=O)COC1=CC=C(N)C(Cl)=C1 PSEULCJHKNCOIU-UHFFFAOYSA-N 0.000 description 8
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 6
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
- DKTRZBWXGOPYIX-UHFFFAOYSA-N 3-chloro-4-nitrophenol Chemical compound OC1=CC=C([N+]([O-])=O)C(Cl)=C1 DKTRZBWXGOPYIX-UHFFFAOYSA-N 0.000 description 5
- 229910052801 chlorine Inorganic materials 0.000 description 5
- 125000001309 chloro group Chemical group Cl* 0.000 description 5
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 5
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 5
- 229910052708 sodium Inorganic materials 0.000 description 5
- 239000011734 sodium Substances 0.000 description 5
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 5
- XOPGTDYRQYSAPC-UHFFFAOYSA-N 2-(3-chloro-4-sulfanylphenoxy)acetic acid Chemical compound ClC=1C=C(OCC(=O)O)C=CC1S XOPGTDYRQYSAPC-UHFFFAOYSA-N 0.000 description 4
- 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 4
- 238000009835 boiling Methods 0.000 description 4
- 239000000460 chlorine Substances 0.000 description 4
- 238000007127 saponification reaction Methods 0.000 description 4
- JKDASQPWUZNCGM-UHFFFAOYSA-N 2-(4-ethenylsulfonylphenoxy)acetic acid Chemical class C(=C)S(=O)(=O)C1=CC=C(OCC(=O)O)C=C1 JKDASQPWUZNCGM-UHFFFAOYSA-N 0.000 description 3
- NOGZGUYAROLJQY-UHFFFAOYSA-N 2-(4-sulfanylphenoxy)acetic acid Chemical compound OC(=O)COC1=CC=C(S)C=C1 NOGZGUYAROLJQY-UHFFFAOYSA-N 0.000 description 3
- 238000002425 crystallisation Methods 0.000 description 3
- 230000008025 crystallization Effects 0.000 description 3
- 238000006704 dehydrohalogenation reaction Methods 0.000 description 3
- 239000002934 diuretic Substances 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 3
- 235000019341 magnesium sulphate Nutrition 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- 125000003396 thiol group Chemical group [H]S* 0.000 description 3
- IQUPABOKLQSFBK-UHFFFAOYSA-N 2-nitrophenol Chemical compound OC1=CC=CC=C1[N+]([O-])=O IQUPABOKLQSFBK-UHFFFAOYSA-N 0.000 description 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 230000001882 diuretic effect Effects 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 239000012259 ether extract Substances 0.000 description 2
- KKSWSRZTAHRZQI-UHFFFAOYSA-N ethyl 2-(3-chloro-4-nitrophenoxy)acetate Chemical compound CCOC(=O)COC1=CC=C([N+]([O-])=O)C(Cl)=C1 KKSWSRZTAHRZQI-UHFFFAOYSA-N 0.000 description 2
- 230000029142 excretion Effects 0.000 description 2
- 239000012530 fluid Substances 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- BRTBNOHXPCEHCO-UHFFFAOYSA-N methyl 2-(3-chloro-4-sulfanylphenoxy)acetate Chemical compound COC(=O)COC1=CC=C(S)C(Cl)=C1 BRTBNOHXPCEHCO-UHFFFAOYSA-N 0.000 description 2
- 230000001452 natriuretic effect Effects 0.000 description 2
- 230000020477 pH reduction Effects 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 229910052717 sulfur Inorganic materials 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- LMEOVPMTQBNCFK-UHFFFAOYSA-N 2-bromobutan-1-ol Chemical compound CCC(Br)CO LMEOVPMTQBNCFK-UHFFFAOYSA-N 0.000 description 1
- RSTZWFWKFSUMLH-UHFFFAOYSA-N 2-nitro-2-phenoxyacetic acid Chemical compound OC(=O)C([N+]([O-])=O)OC1=CC=CC=C1 RSTZWFWKFSUMLH-UHFFFAOYSA-N 0.000 description 1
- OQHWFUQNSLMSBG-UHFFFAOYSA-N 4-amino-2,3-dichlorophenol Chemical compound NC1=CC=C(O)C(Cl)=C1Cl OQHWFUQNSLMSBG-UHFFFAOYSA-N 0.000 description 1
- UBKPLLYABUUFCE-UHFFFAOYSA-N 4-amino-2,3-dimethylphenol Chemical compound CC1=C(C)C(O)=CC=C1N UBKPLLYABUUFCE-UHFFFAOYSA-N 0.000 description 1
- JIRZAMLWKLMYLD-UHFFFAOYSA-N 4-amino-3-bromophenol Chemical compound NC1=CC=C(O)C=C1Br JIRZAMLWKLMYLD-UHFFFAOYSA-N 0.000 description 1
- QGNGOGOOPUYKMC-UHFFFAOYSA-N 4-hydroxy-6-methylaniline Chemical compound CC1=CC(O)=CC=C1N QGNGOGOOPUYKMC-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- FKLJPTJMIBLJAV-UHFFFAOYSA-N Compound IV Chemical compound O1N=C(C)C=C1CCCCCCCOC1=CC=C(C=2OCCN=2)C=C1 FKLJPTJMIBLJAV-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 description 1
- 206010041277 Sodium retention Diseases 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- 230000002159 abnormal effect Effects 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 230000006978 adaptation Effects 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 229910000272 alkali metal oxide Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 125000005907 alkyl ester group Chemical group 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 239000012320 chlorinating reagent Substances 0.000 description 1
- 239000012954 diazonium Substances 0.000 description 1
- 150000001989 diazonium salts Chemical class 0.000 description 1
- 238000006193 diazotization reaction Methods 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- NLFBCYMMUAKCPC-KQQUZDAGSA-N ethyl (e)-3-[3-amino-2-cyano-1-[(e)-3-ethoxy-3-oxoprop-1-enyl]sulfanyl-3-oxoprop-1-enyl]sulfanylprop-2-enoate Chemical compound CCOC(=O)\C=C\SC(=C(C#N)C(N)=O)S\C=C\C(=O)OCC NLFBCYMMUAKCPC-KQQUZDAGSA-N 0.000 description 1
- XZFJBOWDYUWTNY-UHFFFAOYSA-N ethyl 2-(4-amino-3-methylphenoxy)acetate Chemical compound CCOC(=O)COC1=CC=C(N)C(C)=C1 XZFJBOWDYUWTNY-UHFFFAOYSA-N 0.000 description 1
- IBGBOGKPIMZRRU-UHFFFAOYSA-N ethyl 2-(4-aminophenoxy)acetate Chemical compound CCOC(=O)COC1=CC=C(N)C=C1 IBGBOGKPIMZRRU-UHFFFAOYSA-N 0.000 description 1
- NJBWORPRIRNTLH-UHFFFAOYSA-N ethyl 2-(benzenesulfonyl)acetate Chemical compound CCOC(=O)CS(=O)(=O)C1=CC=CC=C1 NJBWORPRIRNTLH-UHFFFAOYSA-N 0.000 description 1
- PQJJJMRNHATNKG-UHFFFAOYSA-N ethyl bromoacetate Chemical compound CCOC(=O)CBr PQJJJMRNHATNKG-UHFFFAOYSA-N 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000011491 glass wool Substances 0.000 description 1
- 125000001475 halogen functional group Chemical group 0.000 description 1
- 230000002140 halogenating effect Effects 0.000 description 1
- 230000003301 hydrolyzing effect Effects 0.000 description 1
- 239000012280 lithium aluminium hydride Substances 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- UMMWLHKJGDUKMB-UHFFFAOYSA-N methyl 2-(3-methyl-4-sulfanylphenoxy)acetate Chemical compound COC(=O)COC1=CC=C(S)C(C)=C1 UMMWLHKJGDUKMB-UHFFFAOYSA-N 0.000 description 1
- OLWMUEMPOVOVLB-UHFFFAOYSA-N methyl 2-(4-sulfanylphenoxy)acetate Chemical compound COC(=O)COC1=CC=C(S)C=C1 OLWMUEMPOVOVLB-UHFFFAOYSA-N 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 239000007800 oxidant agent Substances 0.000 description 1
- 239000008188 pellet Substances 0.000 description 1
- 150000002978 peroxides Chemical class 0.000 description 1
- LCPDWSOZIOUXRV-UHFFFAOYSA-N phenoxyacetic acid Chemical group OC(=O)COC1=CC=CC=C1 LCPDWSOZIOUXRV-UHFFFAOYSA-N 0.000 description 1
- 239000006187 pill Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- JCBJVAJGLKENNC-UHFFFAOYSA-M potassium ethyl xanthate Chemical compound [K+].CCOC([S-])=S JCBJVAJGLKENNC-UHFFFAOYSA-M 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000010288 sodium nitrite Nutrition 0.000 description 1
- 239000011973 solid acid Substances 0.000 description 1
- 239000004071 soot Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 125000004434 sulfur atom Chemical group 0.000 description 1
- 125000004354 sulfur functional group Chemical group 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 231100000816 toxic dose Toxicity 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C317/00—Sulfones; Sulfoxides
- C07C317/16—Sulfones; Sulfoxides having sulfone or sulfoxide groups and singly-bound oxygen atoms bound to the same carbon skeleton
- C07C317/22—Sulfones; Sulfoxides having sulfone or sulfoxide groups and singly-bound oxygen atoms bound to the same carbon skeleton with sulfone or sulfoxide groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C317/00—Sulfones; Sulfoxides
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US29842663A | 1963-07-29 | 1963-07-29 | |
| US452020A US3275685A (en) | 1963-07-29 | 1965-04-29 | [(1-alkenylsulfonyl)phenoxy] alkanoic acids |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NO115333B true NO115333B (xx) | 1968-09-23 |
Family
ID=26970655
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO154170A NO115333B (xx) | 1963-07-29 | 1964-07-28 |
Country Status (11)
| Country | Link |
|---|---|
| US (1) | US3275685A (xx) |
| BE (1) | BE651070A (xx) |
| BR (2) | BR6461186D0 (xx) |
| CH (2) | CH471093A (xx) |
| DE (2) | DE1468340A1 (xx) |
| FR (4) | FR1568705A (xx) |
| GB (2) | GB1040555A (xx) |
| IL (1) | IL21692A (xx) |
| NL (2) | NL6408669A (xx) |
| NO (1) | NO115333B (xx) |
| SE (1) | SE316164B (xx) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3453323A (en) * | 1965-08-02 | 1969-07-01 | Smithkline Corp | 4-(2-haloalkyl)sulfonyl-1-aryloxy-acetic acids |
| US3452093A (en) * | 1966-01-03 | 1969-06-24 | Monsanto Res Corp | Amides |
| DE10222034A1 (de) * | 2002-05-17 | 2003-11-27 | Bayer Ag | Tetrahydroisochinolin-Derivate |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2163180A (en) * | 1934-05-19 | 1939-06-20 | Ig Farbenindustrie Ag | Oxidation of vinyl sulphides |
| US2543648A (en) * | 1943-03-22 | 1951-02-27 | Dow Chemical Co | Manufacture of chloro-olefins |
| US2470077A (en) * | 1948-02-12 | 1949-05-10 | Monsanto Chemicals | Phenylethyl sulfones |
| US3028439A (en) * | 1960-03-23 | 1962-04-03 | Union Carbide Corp | Process for the production of 1, 2, 3-trichloropropene |
-
1964
- 1964-07-12 IL IL21692A patent/IL21692A/xx unknown
- 1964-07-15 GB GB29094/64A patent/GB1040555A/en not_active Expired
- 1964-07-24 DE DE19641468340 patent/DE1468340A1/de active Pending
- 1964-07-28 BR BR161186/64A patent/BR6461186D0/pt unknown
- 1964-07-28 FR FR983326A patent/FR1568705A/fr not_active Expired
- 1964-07-28 BE BE651070D patent/BE651070A/xx unknown
- 1964-07-28 SE SE9162/64A patent/SE316164B/xx unknown
- 1964-07-28 NO NO154170A patent/NO115333B/no unknown
- 1964-07-29 NL NL6408669A patent/NL6408669A/xx unknown
- 1964-07-29 CH CH990664A patent/CH471093A/de not_active IP Right Cessation
- 1964-10-27 FR FR992876A patent/FR4033M/fr not_active Expired
-
1965
- 1965-04-29 US US452020A patent/US3275685A/en not_active Expired - Lifetime
-
1966
- 1966-04-18 FR FR57994A patent/FR1500803A/fr not_active Expired
- 1966-04-19 BR BR178841/66A patent/BR6678841D0/pt unknown
- 1966-04-22 GB GB17763/66A patent/GB1138873A/en not_active Expired
- 1966-04-25 CH CH598166A patent/CH474491A/de not_active IP Right Cessation
- 1966-04-28 DE DE19661593007 patent/DE1593007A1/de active Pending
- 1966-04-29 NL NL6605835A patent/NL6605835A/xx unknown
- 1966-07-15 FR FR69618A patent/FR5637M/fr not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| FR1568705A (xx) | 1969-05-30 |
| IL21692A (en) | 1968-04-25 |
| GB1138873A (en) | 1969-01-01 |
| FR5637M (xx) | 1967-12-18 |
| CH474491A (de) | 1969-06-30 |
| BE651070A (xx) | 1965-01-28 |
| SE316164B (xx) | 1969-10-20 |
| DE1593007A1 (de) | 1970-04-23 |
| BR6678841D0 (pt) | 1973-09-18 |
| FR4033M (xx) | 1966-03-28 |
| CH471093A (de) | 1969-04-15 |
| DE1468340A1 (de) | 1968-12-19 |
| NL6408669A (xx) | 1965-02-01 |
| FR1500803A (fr) | 1967-11-10 |
| GB1040555A (en) | 1966-09-01 |
| BR6461186D0 (pt) | 1973-08-02 |
| US3275685A (en) | 1966-09-27 |
| NL6605835A (xx) | 1966-10-31 |
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