NO127149B - - Google Patents
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- Publication number
- NO127149B NO127149B NO02353/70A NO235370A NO127149B NO 127149 B NO127149 B NO 127149B NO 02353/70 A NO02353/70 A NO 02353/70A NO 235370 A NO235370 A NO 235370A NO 127149 B NO127149 B NO 127149B
- Authority
- NO
- Norway
- Prior art keywords
- acid
- formula
- salt
- lower alkyl
- reacted
- Prior art date
Links
- 239000002253 acid Substances 0.000 claims description 12
- 150000003839 salts Chemical class 0.000 claims description 10
- 238000000034 method Methods 0.000 claims description 8
- 238000002360 preparation method Methods 0.000 claims description 6
- -1 methylenebisphenol compound Chemical class 0.000 claims description 5
- 125000005907 alkyl ester group Chemical group 0.000 claims description 4
- 239000000460 chlorine Substances 0.000 claims description 4
- 229910052801 chlorine Inorganic materials 0.000 claims description 3
- 239000001257 hydrogen Substances 0.000 claims description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims description 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- 150000007529 inorganic bases Chemical class 0.000 claims description 2
- 150000004702 methyl esters Chemical class 0.000 claims description 2
- 150000007530 organic bases Chemical class 0.000 claims description 2
- 125000001309 chloro group Chemical group Cl* 0.000 claims 1
- 150000002431 hydrogen Chemical class 0.000 claims 1
- 230000020477 pH reduction Effects 0.000 claims 1
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims 1
- 230000001225 therapeutic effect Effects 0.000 claims 1
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 15
- 150000001875 compounds Chemical class 0.000 description 11
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- 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 8
- 239000002904 solvent Substances 0.000 description 7
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- 150000002148 esters Chemical class 0.000 description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- 239000003125 aqueous solvent Substances 0.000 description 4
- JXTHNDFMNIQAHM-UHFFFAOYSA-N dichloroacetic acid Chemical compound OC(=O)C(Cl)Cl JXTHNDFMNIQAHM-UHFFFAOYSA-N 0.000 description 4
- 235000005911 diet Nutrition 0.000 description 4
- 230000037213 diet Effects 0.000 description 4
- NIJGVVHCUXNSLL-UHFFFAOYSA-N ethyl 2,2-dibromoacetate Chemical compound CCOC(=O)C(Br)Br NIJGVVHCUXNSLL-UHFFFAOYSA-N 0.000 description 4
- 238000002844 melting Methods 0.000 description 4
- 230000008018 melting Effects 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 208000024172 Cardiovascular disease Diseases 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 239000002585 base Substances 0.000 description 3
- 239000008280 blood Substances 0.000 description 3
- 210000004369 blood Anatomy 0.000 description 3
- 238000009835 boiling Methods 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 230000003595 spectral effect Effects 0.000 description 3
- UFTFJSFQGQCHQW-UHFFFAOYSA-N triformin Chemical compound O=COCC(OC=O)COC=O UFTFJSFQGQCHQW-UHFFFAOYSA-N 0.000 description 3
- MQCPOLNSJCWPGT-UHFFFAOYSA-N 2,2'-Bisphenol F Chemical compound OC1=CC=CC=C1CC1=CC=CC=C1O MQCPOLNSJCWPGT-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- 229930185605 Bisphenol Natural products 0.000 description 2
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 2
- 241000700159 Rattus Species 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- 150000001408 amides Chemical class 0.000 description 2
- 208000011775 arteriosclerosis disease Diseases 0.000 description 2
- 235000012000 cholesterol Nutrition 0.000 description 2
- 208000029078 coronary artery disease Diseases 0.000 description 2
- 230000034994 death Effects 0.000 description 2
- 231100000517 death Toxicity 0.000 description 2
- 229960005215 dichloroacetic acid Drugs 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 150000002632 lipids Chemical class 0.000 description 2
- XGZVUEUWXADBQD-UHFFFAOYSA-L lithium carbonate Chemical compound [Li+].[Li+].[O-]C([O-])=O XGZVUEUWXADBQD-UHFFFAOYSA-L 0.000 description 2
- 229910052808 lithium carbonate Inorganic materials 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 229910000027 potassium carbonate Inorganic materials 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 230000035484 reaction time Effects 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 150000003626 triacylglycerols Chemical class 0.000 description 2
- WXNZTHHGJRFXKQ-UHFFFAOYSA-N 4-chlorophenol Chemical compound OC1=CC=C(Cl)C=C1 WXNZTHHGJRFXKQ-UHFFFAOYSA-N 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
- 102000004895 Lipoproteins Human genes 0.000 description 1
- 108090001030 Lipoproteins Proteins 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 241000700157 Rattus norvegicus Species 0.000 description 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 description 1
- 239000000920 calcium hydroxide Substances 0.000 description 1
- 229910001861 calcium hydroxide Inorganic materials 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 238000012754 cardiac puncture Methods 0.000 description 1
- 230000002490 cerebral effect Effects 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- NPOMSUOUAZCMBL-UHFFFAOYSA-N dichloromethane;ethoxyethane Chemical compound ClCCl.CCOCC NPOMSUOUAZCMBL-UHFFFAOYSA-N 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- ZKQFHRVKCYFVCN-UHFFFAOYSA-N ethoxyethane;hexane Chemical compound CCOCC.CCCCCC ZKQFHRVKCYFVCN-UHFFFAOYSA-N 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 244000144993 groups of animals Species 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- ACGUYXCXAPNIKK-UHFFFAOYSA-N hexachlorophene Chemical compound OC1=C(Cl)C=C(Cl)C(Cl)=C1CC1=C(O)C(Cl)=CC(Cl)=C1Cl ACGUYXCXAPNIKK-UHFFFAOYSA-N 0.000 description 1
- 150000004678 hydrides Chemical class 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- HKMLRUAPIDAGIE-UHFFFAOYSA-N methyl 2,2-dichloroacetate Chemical compound COC(=O)C(Cl)Cl HKMLRUAPIDAGIE-UHFFFAOYSA-N 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 150000003751 zinc Chemical class 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D321/00—Heterocyclic compounds containing rings having two oxygen atoms as the only ring hetero atoms, not provided for by groups C07D317/00 - C07D319/00
- C07D321/12—Eight-membered rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US83455469A | 1969-06-18 | 1969-06-18 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NO127149B true NO127149B (de) | 1973-05-14 |
Family
ID=25267192
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO02353/70A NO127149B (de) | 1969-06-18 | 1970-06-17 |
Country Status (14)
| Country | Link |
|---|---|
| US (1) | US3553234A (de) |
| BE (1) | BE752209A (de) |
| CH (1) | CH518926A (de) |
| DE (1) | DE2029796A1 (de) |
| ES (1) | ES380859A1 (de) |
| FR (1) | FR2052986B1 (de) |
| GB (1) | GB1265279A (de) |
| IE (1) | IE34314B1 (de) |
| IL (1) | IL34685A (de) |
| LU (1) | LU61155A1 (de) |
| NL (1) | NL7008743A (de) |
| NO (1) | NO127149B (de) |
| SE (1) | SE367821B (de) |
| ZA (1) | ZA703904B (de) |
Families Citing this family (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3931173A (en) * | 1971-07-22 | 1976-01-06 | Richardson-Merrell Inc. | Dioxocin carboxamide derivatives |
| FR2146895B1 (de) * | 1971-07-23 | 1974-09-06 | Crt | |
| BE788770A (fr) * | 1971-09-13 | 1973-01-02 | Richardson Merrell Inc | Nouveaux acides dioxathiocinecarboxyliques et leurs derives utiles notamment comme hypolipemiants et agents antiinfectieux |
| US3872105A (en) * | 1973-06-11 | 1975-03-18 | Merrell Inc Richard | Derivatives of 1,3-benzodioxole-2-carboxylic acid |
| US4938790A (en) * | 1989-06-15 | 1990-07-03 | The Dow Chemical Company | Herbicidal 12-substituted 12H-dibenzo(D,G)(1,3)dioxocin-6-carboxylic acids |
| US5158597A (en) * | 1989-06-15 | 1992-10-27 | The Dow Chemical Company | Herbicidal 12-substituted 12H-dibenzo[d,g]dioxocin-6-carboxylic acids |
| US4979978A (en) * | 1989-06-15 | 1990-12-25 | The Dow Chemical Company | Herbicidal 12H-dibenzo[d,g][1,3]dioxocin-6-carboxylic acids |
| US4976770A (en) * | 1989-06-29 | 1990-12-11 | Fermenta Asc Corporation | Herbicidal and plant growth regulant activity of glyoxylates |
| JPH04501859A (ja) * | 1989-06-29 | 1992-04-02 | アイエスケー・バイオテック・コーポレーション | 新規なグリオキシレートおよびグリオキシレート活性化植物成長調整活性剤 |
| US4999448A (en) * | 1990-04-12 | 1991-03-12 | The Dow Chemical Company | Method of preparing bis-phenol ethers |
-
1969
- 1969-06-18 US US834554A patent/US3553234A/en not_active Expired - Lifetime
-
1970
- 1970-06-08 ZA ZA703904A patent/ZA703904B/xx unknown
- 1970-06-09 IL IL34685A patent/IL34685A/xx unknown
- 1970-06-15 NL NL7008743A patent/NL7008743A/xx unknown
- 1970-06-16 GB GB1265279D patent/GB1265279A/en not_active Expired
- 1970-06-16 DE DE19702029796 patent/DE2029796A1/de active Pending
- 1970-06-17 ES ES380859A patent/ES380859A1/es not_active Expired
- 1970-06-17 IE IE791/70A patent/IE34314B1/xx unknown
- 1970-06-17 SE SE08425/70A patent/SE367821B/xx unknown
- 1970-06-17 NO NO02353/70A patent/NO127149B/no unknown
- 1970-06-18 FR FR7022533A patent/FR2052986B1/fr not_active Expired
- 1970-06-18 LU LU61155D patent/LU61155A1/xx unknown
- 1970-06-18 CH CH926970A patent/CH518926A/fr not_active IP Right Cessation
- 1970-06-18 BE BE752209D patent/BE752209A/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| US3553234A (en) | 1971-01-05 |
| FR2052986B1 (de) | 1974-08-30 |
| CH518926A (fr) | 1972-02-15 |
| BE752209A (fr) | 1970-12-01 |
| IL34685A0 (en) | 1970-08-19 |
| NL7008743A (de) | 1970-12-22 |
| IL34685A (en) | 1973-04-30 |
| IE34314B1 (en) | 1975-04-02 |
| DE2029796A1 (de) | 1971-01-07 |
| ZA703904B (en) | 1971-03-31 |
| LU61155A1 (de) | 1971-07-02 |
| GB1265279A (de) | 1972-03-01 |
| ES380859A1 (es) | 1973-04-01 |
| FR2052986A1 (de) | 1971-04-16 |
| IE34314L (en) | 1970-12-18 |
| SE367821B (de) | 1974-06-10 |
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