CH617194A5 - - Google Patents
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- Publication number
- CH617194A5 CH617194A5 CH1534474A CH1534474A CH617194A5 CH 617194 A5 CH617194 A5 CH 617194A5 CH 1534474 A CH1534474 A CH 1534474A CH 1534474 A CH1534474 A CH 1534474A CH 617194 A5 CH617194 A5 CH 617194A5
- Authority
- CH
- Switzerland
- Prior art keywords
- group
- compounds
- formula
- light petroleum
- compound
- Prior art date
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- 150000001875 compounds Chemical class 0.000 claims description 28
- -1 (Ci-CO-alkyl Chemical group 0.000 claims description 13
- 238000000034 method Methods 0.000 claims description 9
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 9
- 125000004432 carbon atom Chemical group C* 0.000 claims description 6
- 125000000217 alkyl group Chemical group 0.000 claims description 5
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 5
- 229910052799 carbon Inorganic materials 0.000 claims description 4
- 125000000532 dioxanyl group Chemical group 0.000 claims description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 4
- 150000003839 salts Chemical class 0.000 claims description 4
- 239000002904 solvent Substances 0.000 claims description 4
- 125000003545 alkoxy group Chemical group 0.000 claims description 3
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 3
- 125000005843 halogen group Chemical group 0.000 claims description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
- 125000001424 substituent group Chemical group 0.000 claims description 3
- 239000003377 acid catalyst Substances 0.000 claims description 2
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 2
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims description 2
- 229910052987 metal hydride Inorganic materials 0.000 claims description 2
- 150000004681 metal hydrides Chemical class 0.000 claims description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
- 238000002360 preparation method Methods 0.000 claims description 2
- RZVAJINKPMORJF-UHFFFAOYSA-N Acetaminophen Chemical compound CC(=O)NC1=CC=C(O)C=C1 RZVAJINKPMORJF-UHFFFAOYSA-N 0.000 claims 3
- 208000002193 Pain Diseases 0.000 claims 2
- 230000000694 effects Effects 0.000 claims 2
- 229960005489 paracetamol Drugs 0.000 claims 2
- 230000035945 sensitivity Effects 0.000 claims 2
- RLQZIECDMISZHS-UHFFFAOYSA-N 2-phenylcyclohexa-2,5-diene-1,4-dione Chemical compound O=C1C=CC(=O)C(C=2C=CC=CC=2)=C1 RLQZIECDMISZHS-UHFFFAOYSA-N 0.000 claims 1
- 206010006811 Bursitis Diseases 0.000 claims 1
- 241000282693 Cercopithecidae Species 0.000 claims 1
- 206010010904 Convulsion Diseases 0.000 claims 1
- 206010019233 Headaches Diseases 0.000 claims 1
- 208000000112 Myalgia Diseases 0.000 claims 1
- 230000000202 analgesic effect Effects 0.000 claims 1
- 230000001754 anti-pyretic effect Effects 0.000 claims 1
- 238000009833 condensation Methods 0.000 claims 1
- 230000005494 condensation Effects 0.000 claims 1
- 230000036461 convulsion Effects 0.000 claims 1
- 230000002526 effect on cardiovascular system Effects 0.000 claims 1
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 claims 1
- 231100000869 headache Toxicity 0.000 claims 1
- 239000007928 intraperitoneal injection Substances 0.000 claims 1
- 208000013465 muscle pain Diseases 0.000 claims 1
- 239000004081 narcotic agent Substances 0.000 claims 1
- 231100000252 nontoxic Toxicity 0.000 claims 1
- 230000003000 nontoxic effect Effects 0.000 claims 1
- 230000000638 stimulation 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
- 208000004371 toothache Diseases 0.000 claims 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 71
- 239000003208 petroleum Substances 0.000 description 58
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 43
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 36
- 235000019439 ethyl acetate Nutrition 0.000 description 32
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 16
- 239000000243 solution Substances 0.000 description 16
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 15
- 239000000203 mixture Substances 0.000 description 11
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 8
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 8
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 238000010992 reflux Methods 0.000 description 6
- CITZTYCVNHPCQL-UHFFFAOYSA-N 4-hydroxy-3-(hydroxymethyl)-3-methylbutan-2-one Chemical compound CC(=O)C(C)(CO)CO CITZTYCVNHPCQL-UHFFFAOYSA-N 0.000 description 5
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 5
- 239000013078 crystal Substances 0.000 description 5
- 239000012280 lithium aluminium hydride Substances 0.000 description 5
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
- 150000001299 aldehydes Chemical class 0.000 description 4
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 4
- 239000000706 filtrate Substances 0.000 description 4
- 239000002002 slurry Substances 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 3
- 239000012043 crude product Substances 0.000 description 3
- 239000003921 oil Substances 0.000 description 3
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 description 2
- NDOSBRPFYGAOHP-UHFFFAOYSA-N 1-(2-methyl-5-pentyl-1,3-dioxan-5-yl)ethanone Chemical compound C(CCCC)C1(COC(OC1)C)C(=O)C NDOSBRPFYGAOHP-UHFFFAOYSA-N 0.000 description 2
- KBZLWCPDLSPRFW-UHFFFAOYSA-N 1-[2-(4-methoxyphenyl)-5-methyl-1,3-dioxan-5-yl]ethanone Chemical compound C1=CC(OC)=CC=C1C1OCC(C)(C(C)=O)CO1 KBZLWCPDLSPRFW-UHFFFAOYSA-N 0.000 description 2
- DTNCEVHDMVPBRX-UHFFFAOYSA-N 2,2-bis(hydroxymethyl)cycloheptan-1-one Chemical compound OCC1(CO)CCCCCC1=O DTNCEVHDMVPBRX-UHFFFAOYSA-N 0.000 description 2
- ZPVFWPFBNIEHGJ-UHFFFAOYSA-N 2-octanone Chemical compound CCCCCCC(C)=O ZPVFWPFBNIEHGJ-UHFFFAOYSA-N 0.000 description 2
- BIECKCJPCYPAMM-UHFFFAOYSA-N 3,3-bis(hydroxymethyl)octan-2-one Chemical compound CCCCCC(CO)(CO)C(C)=O BIECKCJPCYPAMM-UHFFFAOYSA-N 0.000 description 2
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 description 2
- IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 description 2
- RGSFGYAAUTVSQA-UHFFFAOYSA-N Cyclopentane Chemical compound C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 description 2
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 2
- 239000012230 colorless oil Substances 0.000 description 2
- 238000002425 crystallisation Methods 0.000 description 2
- 230000008025 crystallization Effects 0.000 description 2
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 2
- BGTOWKSIORTVQH-UHFFFAOYSA-N cyclopentanone Chemical compound O=C1CCCC1 BGTOWKSIORTVQH-UHFFFAOYSA-N 0.000 description 2
- 239000000284 extract Substances 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 150000002576 ketones Chemical class 0.000 description 2
- ZRSNZINYAWTAHE-UHFFFAOYSA-N p-methoxybenzaldehyde Chemical compound COC1=CC=C(C=O)C=C1 ZRSNZINYAWTAHE-UHFFFAOYSA-N 0.000 description 2
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 2
- 235000017557 sodium bicarbonate Nutrition 0.000 description 2
- 229910000029 sodium carbonate Inorganic materials 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- DYLIWHYUXAJDOJ-OWOJBTEDSA-N (e)-4-(6-aminopurin-9-yl)but-2-en-1-ol Chemical compound NC1=NC=NC2=C1N=CN2C\C=C\CO DYLIWHYUXAJDOJ-OWOJBTEDSA-N 0.000 description 1
- ZUZMJTZSKXJVPQ-UHFFFAOYSA-N 1-[2-(4-fluorophenyl)-5-methyl-1,3-dioxan-5-yl]ethanone Chemical compound FC1=CC=C(C=C1)C1OCC(CO1)(C)C(=O)C ZUZMJTZSKXJVPQ-UHFFFAOYSA-N 0.000 description 1
- SFABUIKDOPBFFM-UHFFFAOYSA-N 1-[2-[4-(dimethylamino)phenyl]-5-methyl-1,3-dioxan-5-yl]ethanone Chemical compound CN(C1=CC=C(C=C1)C1OCC(CO1)(C)C(=O)C)C SFABUIKDOPBFFM-UHFFFAOYSA-N 0.000 description 1
- MDSWTWGXRGHUIO-UHFFFAOYSA-N 1-[5-methyl-2-(3-nitrophenyl)-1,3-dioxan-5-yl]ethanone Chemical compound O1CC(C(=O)C)(C)COC1C1=CC=CC([N+]([O-])=O)=C1 MDSWTWGXRGHUIO-UHFFFAOYSA-N 0.000 description 1
- WFOONLYADDEHOQ-UHFFFAOYSA-N 1-[5-methyl-2-(4-methylphenyl)-1,3-dioxan-5-yl]ethanone Chemical compound CC1=CC=C(C=C1)C1OCC(CO1)(C)C(=O)C WFOONLYADDEHOQ-UHFFFAOYSA-N 0.000 description 1
- FXWFZIRWWNPPOV-UHFFFAOYSA-N 2-aminobenzaldehyde Chemical compound NC1=CC=CC=C1C=O FXWFZIRWWNPPOV-UHFFFAOYSA-N 0.000 description 1
- UOQXIWFBQSVDPP-UHFFFAOYSA-N 4-fluorobenzaldehyde Chemical compound FC1=CC=C(C=O)C=C1 UOQXIWFBQSVDPP-UHFFFAOYSA-N 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- OPFTUNCRGUEPRZ-QLFBSQMISA-N Cyclohexane Natural products CC(=C)[C@@H]1CC[C@@](C)(C=C)[C@H](C(C)=C)C1 OPFTUNCRGUEPRZ-QLFBSQMISA-N 0.000 description 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 239000012267 brine Substances 0.000 description 1
- 238000006482 condensation reaction Methods 0.000 description 1
- 239000010779 crude oil Substances 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- RXKJFZQQPQGTFL-UHFFFAOYSA-N dihydroxyacetone Chemical class OCC(=O)CO RXKJFZQQPQGTFL-UHFFFAOYSA-N 0.000 description 1
- 125000002541 furyl group Chemical group 0.000 description 1
- 238000001030 gas--liquid chromatography Methods 0.000 description 1
- DMEGYFMYUHOHGS-UHFFFAOYSA-N heptamethylene Natural products C1CCCCCC1 DMEGYFMYUHOHGS-UHFFFAOYSA-N 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- JMMWKPVZQRWMSS-UHFFFAOYSA-N isopropanol acetate Natural products CC(C)OC(C)=O JMMWKPVZQRWMSS-UHFFFAOYSA-N 0.000 description 1
- 229940011051 isopropyl acetate Drugs 0.000 description 1
- GWYFCOCPABKNJV-UHFFFAOYSA-M isovalerate Chemical compound CC(C)CC([O-])=O GWYFCOCPABKNJV-UHFFFAOYSA-M 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 229910000033 sodium borohydride Inorganic materials 0.000 description 1
- 239000012279 sodium borohydride Substances 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D319/00—Heterocyclic compounds containing six-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D319/04—1,3-Dioxanes; Hydrogenated 1,3-dioxanes
- C07D319/08—1,3-Dioxanes; Hydrogenated 1,3-dioxanes condensed with carbocyclic rings or ring systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
- C07C45/67—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton
- C07C45/68—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms
- C07C45/72—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms by reaction of compounds containing >C = O groups with the same or other compounds containing >C = O groups
- C07C45/75—Reactions with formaldehyde
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/04—Saturated compounds containing keto groups bound to acyclic carbon atoms
- C07C49/17—Saturated compounds containing keto groups bound to acyclic carbon atoms containing hydroxy groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D319/00—Heterocyclic compounds containing six-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D319/04—1,3-Dioxanes; Hydrogenated 1,3-dioxanes
- C07D319/06—1,3-Dioxanes; Hydrogenated 1,3-dioxanes not condensed with other rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Heterocyclic Compounds That Contain Two Or More Ring Oxygen Atoms (AREA)
- Plural Heterocyclic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB5392473A GB1448458A (en) | 1973-11-21 | 1973-11-21 | 1,3-dioxan derivatives and pharmaceutical compositions thereof |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH617194A5 true CH617194A5 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1980-05-14 |
Family
ID=10469419
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH1534474A CH617194A5 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1973-11-21 | 1974-11-18 |
Country Status (12)
Families Citing this family (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4322354A (en) * | 1979-03-05 | 1982-03-30 | Timex Corporation | 5-Substituted-2-(4-cyanophenyl)-1,3,-dioxanes |
| US4298528A (en) * | 1980-03-28 | 1981-11-03 | Timex Corporation | Cyclohexyl-dioxane liquid crystalline compounds |
| US4313878A (en) * | 1980-12-03 | 1982-02-02 | Timex Corporation | 4-Substituted phenyl 4'-(5-n-alkyl-1,3-dioxan-2-yl)benzoates |
| US4325830A (en) * | 1980-12-24 | 1982-04-20 | Timex Corporation | Three ring dioxane liquid crystalline compounds |
| DE3119201A1 (de) * | 1981-05-14 | 1982-12-09 | Basf Ag, 6700 Ludwigshafen | Substituierte 1,3-dioxane, verfahren zu ihrer herstellung, diese enthaltende herbizide und ihre anwendung als herbizide |
| JPS6036479A (ja) * | 1983-08-08 | 1985-02-25 | Kotobuki Seiyaku Kk | １，３−ジオキサン誘導体、本化合物を有効成分とする抗潰瘍剤及びその製造方法 |
| GB8531892D0 (en) * | 1985-12-30 | 1986-02-05 | Ici Plc | Carboxylic acids |
| US4861764A (en) * | 1986-11-17 | 1989-08-29 | Macro Chem. Corp. | Percutaneous absorption enhancers, compositions containing same and method of use |
| US5175143A (en) * | 1987-01-29 | 1992-12-29 | Unilever Patent Holdings B.V. | Perfumery materials |
| US5292763A (en) * | 1989-11-03 | 1994-03-08 | Rohm And Haas Company | Synergistic microbicidal combinations containing 4,5-dichloro-2-octyl-3-isothiazolone and certain commercial biocides |
| US5468759A (en) * | 1991-12-19 | 1995-11-21 | Rohm And Haas Company | Synergistic microbicidal combinations containing 4,5-dichloro-2-octyl-3-isothiazolone and certain commercial biocides |
| US5620980A (en) * | 1995-02-22 | 1997-04-15 | Macrochem Corporation | Method for treating hair loss |
| US5728848A (en) * | 1996-03-11 | 1998-03-17 | Council Of Scientific & Industrial Research | 9-hydroxymethyl-7,12 dioxaspiro 5,6!dodecane, novel 9-(2-hydroxyethyl-7,11-dioxaspiro 5,5!undecane and a process for preparing said 9-(2-hydroxyethyl-7,11 dioxaspiro 5,5!undecane |
| US8324407B2 (en) | 2009-01-30 | 2012-12-04 | Mitsubishi Gas Chemical Company, Inc. | Alcohol compound having dioxane structure and process for producing same |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA475546A (en) * | 1951-07-24 | Standard Oil Development Company | Metadioxanes produced from aldehydes and olefinic compounds | |
| US3000905A (en) * | 1959-01-02 | 1961-09-19 | Atlantic Refining Co | Production of hydroxymethyl-dimethyl-meta-dioxanes |
| US3454596A (en) * | 1964-06-03 | 1969-07-08 | Mobil Oil Corp | Addition reactions to carbonyl compounds |
| JPS4320012Y1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) * | 1965-05-26 | 1968-08-22 | ||
| SE323391B (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) * | 1967-01-25 | 1970-05-04 | Perstorp Ab | |
| DE1905258A1 (de) * | 1969-02-04 | 1970-08-06 | Dynamit Nobel Ag | Ketonitrile und Verfahren zu deren Herstellung |
| IT988012B (it) * | 1970-03-25 | 1975-04-10 | Dynamit Nobel Ag | Procedimento per la produzione di acetali ciclici di benzofenone |
| FR2121459B1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) * | 1971-01-08 | 1973-11-30 | Pepro | |
| GB1401978A (en) * | 1971-11-29 | 1975-08-06 | Shell Int Research | Substituted cyclic 1,3-diethers and their use as herbicides |
-
1973
- 1973-11-21 GB GB5392473A patent/GB1448458A/en not_active Expired
-
1974
- 1974-11-07 IE IE2289/74A patent/IE40539B1/xx unknown
- 1974-11-11 ZA ZA00747219A patent/ZA747219B/xx unknown
- 1974-11-12 US US05/523,238 patent/US4085222A/en not_active Expired - Lifetime
- 1974-11-15 DE DE19742454281 patent/DE2454281A1/de not_active Withdrawn
- 1974-11-18 CH CH1534474A patent/CH617194A5/de not_active IP Right Cessation
- 1974-11-19 BE BE150636A patent/BE822345A/xx unknown
- 1974-11-20 FR FR7438124A patent/FR2251324B1/fr not_active Expired
- 1974-11-20 DK DK604574A patent/DK604574A/da unknown
- 1974-11-20 SE SE7414595A patent/SE407575B/xx unknown
- 1974-11-21 NL NL7415163A patent/NL7415163A/xx not_active Application Discontinuation
- 1974-11-21 JP JP49135057A patent/JPS5083377A/ja active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| ZA747219B (en) | 1975-11-26 |
| GB1448458A (en) | 1976-09-08 |
| SE407575B (sv) | 1979-04-02 |
| BE822345A (fr) | 1975-05-20 |
| FR2251324B1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1978-06-30 |
| DE2454281A1 (de) | 1975-05-22 |
| SE7414595L (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1975-05-22 |
| IE40539L (en) | 1975-05-21 |
| US4085222A (en) | 1978-04-18 |
| AU7536474A (en) | 1976-05-20 |
| JPS5083377A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1975-07-05 |
| NL7415163A (nl) | 1975-05-23 |
| FR2251324A1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1975-06-13 |
| IE40539B1 (en) | 1979-06-20 |
| DK604574A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1975-07-21 |
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