DE2306118C3 - S-Methyl-lO-methylen^-dioxatricyclo [43,1,037I decane und 3,10-Dimethyl2,9-dioxatricyclo [43,1, 03·7! decane sowie Verfahren zu deren Herstellung - Google Patents
S-Methyl-lO-methylen^-dioxatricyclo [43,1,037I decane und 3,10-Dimethyl2,9-dioxatricyclo [43,1, 03·7! decane sowie Verfahren zu deren HerstellungInfo
- Publication number
- DE2306118C3 DE2306118C3 DE2306118A DE2306118A DE2306118C3 DE 2306118 C3 DE2306118 C3 DE 2306118C3 DE 2306118 A DE2306118 A DE 2306118A DE 2306118 A DE2306118 A DE 2306118A DE 2306118 C3 DE2306118 C3 DE 2306118C3
- Authority
- DE
- Germany
- Prior art keywords
- decane
- dioxatricyclo
- methyl
- methoxy
- hydroxy
- 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
Links
- DIOQZVSQGTUSAI-UHFFFAOYSA-N decane Chemical compound CCCCCCCCCC DIOQZVSQGTUSAI-UHFFFAOYSA-N 0.000 title description 55
- 238000000034 method Methods 0.000 title description 9
- 230000008569 process Effects 0.000 title description 5
- 238000004519 manufacturing process Methods 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 description 29
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 24
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 13
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 12
- 206010002091 Anaesthesia Diseases 0.000 description 10
- 230000037005 anaesthesia Effects 0.000 description 10
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 8
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 8
- 125000000217 alkyl group Chemical group 0.000 description 6
- 125000004432 carbon atom Chemical group C* 0.000 description 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 6
- JOYRKODLDBILNP-UHFFFAOYSA-N urethane group Chemical group NC(=O)OCC JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 6
- 206010003591 Ataxia Diseases 0.000 description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
- -1 alkyl isocyanate Chemical class 0.000 description 5
- 239000007858 starting material Substances 0.000 description 5
- UYXAWHWODHRRMR-UHFFFAOYSA-N hexobarbital Chemical compound O=C1N(C)C(=O)NC(=O)C1(C)C1=CCCCC1 UYXAWHWODHRRMR-UHFFFAOYSA-N 0.000 description 4
- 229960002456 hexobarbital Drugs 0.000 description 4
- 239000012948 isocyanate Substances 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- 238000002360 preparation method Methods 0.000 description 4
- 239000000932 sedative agent Substances 0.000 description 4
- GSLTVFIVJMCNBH-UHFFFAOYSA-N 2-isocyanatopropane Chemical compound CC(C)N=C=O GSLTVFIVJMCNBH-UHFFFAOYSA-N 0.000 description 3
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 3
- 229960000583 acetic acid Drugs 0.000 description 3
- MKJDUHZPLQYUCB-UHFFFAOYSA-N decan-4-one Chemical compound CCCCCCC(=O)CCC MKJDUHZPLQYUCB-UHFFFAOYSA-N 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- WUDNUHPRLBTKOJ-UHFFFAOYSA-N ethyl isocyanate Chemical compound CCN=C=O WUDNUHPRLBTKOJ-UHFFFAOYSA-N 0.000 description 3
- 230000000147 hypnotic effect Effects 0.000 description 3
- 230000003533 narcotic effect Effects 0.000 description 3
- 230000001624 sedative effect Effects 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 241000282472 Canis lupus familiaris Species 0.000 description 2
- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 description 2
- 241000282326 Felis catus Species 0.000 description 2
- 241001465754 Metazoa Species 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- 230000009471 action Effects 0.000 description 2
- 125000003545 alkoxy group Chemical group 0.000 description 2
- 230000003444 anaesthetic effect Effects 0.000 description 2
- 229940125717 barbiturate Drugs 0.000 description 2
- 230000008901 benefit Effects 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 239000005457 ice water Substances 0.000 description 2
- 229910052987 metal hydride Inorganic materials 0.000 description 2
- 150000004681 metal hydrides Chemical class 0.000 description 2
- 239000004081 narcotic agent Substances 0.000 description 2
- 230000003389 potentiating effect Effects 0.000 description 2
- 230000009467 reduction Effects 0.000 description 2
- 229910052938 sodium sulfate Inorganic materials 0.000 description 2
- 235000011152 sodium sulphate Nutrition 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- 230000001960 triggered effect Effects 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- 229910010082 LiAlH Inorganic materials 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- SMZOGRDCAXLAAR-UHFFFAOYSA-N aluminium isopropoxide Chemical compound [Al+3].CC(C)[O-].CC(C)[O-].CC(C)[O-] SMZOGRDCAXLAAR-UHFFFAOYSA-N 0.000 description 1
- BFNBIHQBYMNNAN-UHFFFAOYSA-N ammonium sulfate Chemical compound N.N.OS(O)(=O)=O BFNBIHQBYMNNAN-UHFFFAOYSA-N 0.000 description 1
- 229910052921 ammonium sulfate Inorganic materials 0.000 description 1
- 239000001166 ammonium sulphate Substances 0.000 description 1
- 235000011130 ammonium sulphate Nutrition 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 230000001773 anti-convulsant effect Effects 0.000 description 1
- 230000036983 biotransformation Effects 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 239000003874 central nervous system depressant Substances 0.000 description 1
- 239000003610 charcoal Substances 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- DTDMYWXTWWFLGJ-UHFFFAOYSA-N decan-4-ol Chemical class CCCCCCC(O)CCC DTDMYWXTWWFLGJ-UHFFFAOYSA-N 0.000 description 1
- 230000003001 depressive effect Effects 0.000 description 1
- 231100000673 dose–response relationship Toxicity 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 239000012259 ether extract Substances 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 239000003326 hypnotic agent Substances 0.000 description 1
- 238000007912 intraperitoneal administration Methods 0.000 description 1
- 238000001990 intravenous administration Methods 0.000 description 1
- 230000002045 lasting effect Effects 0.000 description 1
- 239000012280 lithium aluminium hydride Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 210000001034 respiratory center Anatomy 0.000 description 1
- 229940125723 sedative agent Drugs 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 238000001665 trituration Methods 0.000 description 1
- 229940124549 vasodilator Drugs 0.000 description 1
- 239000003071 vasodilator agent Substances 0.000 description 1
- 230000001457 vasomotor Effects 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D493/00—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system
- C07D493/02—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system in which the condensed system contains two hetero rings
- C07D493/08—Bridged systems
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)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Priority Applications (28)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2306118A DE2306118C3 (de) | 1973-02-08 | 1973-02-08 | S-Methyl-lO-methylen^-dioxatricyclo [43,1,037I decane und 3,10-Dimethyl2,9-dioxatricyclo [43,1, 03·7! decane sowie Verfahren zu deren Herstellung |
| DE2362396A DE2362396C2 (de) | 1973-02-08 | 1973-12-15 | 3-Methyl-10-methylen-2,9-dioxatricyclo[4,3,1,0↑3↑,↑7↑] decane |
| FI3983/73A FI56533C (fi) | 1973-02-08 | 1973-12-27 | Saett att framstaella nya 4alfa-karbamyloxi-8-alkoxi-10-metylen-3-metyl-2,9-dioxatricyklo(4,3,1,03,7)-dekaner |
| CH19374A CH603657A5 (enrdf_load_stackoverflow) | 1973-02-08 | 1974-01-08 | |
| NLAANVRAGE7400404,A NL183011C (nl) | 1973-02-08 | 1974-01-11 | Werkwijze voor het bereiden van een geneesmiddel met werking op het centrale zenuwstelsel; werkwijze voor het bereiden van een geneeskrachtige verbinding die geschikt is om daarbij te worden gebruikt; therapeutisch voorwerp. |
| GB254874A GB1436821A (en) | 1973-02-08 | 1974-01-18 | 4-hydroxy-2,9-dioxatricyclo 4,3,1,0-3,7- decane esters |
| BE140441A BE810475A (fr) | 1973-02-08 | 1974-01-31 | 4-hydroxy-2,9-dioxatricyclo (4,3,1,03,7) decanes et leurs esters |
| ES422841A ES422841A1 (es) | 1973-02-08 | 1974-02-01 | Procedimiento de preparacion de esteres de 4-hidroxi-2,9- dioxatriciclo (4, 3, 03,7)-decanos. |
| IE196/74A IE38815B1 (en) | 1973-02-08 | 1974-02-04 | 4-hydroxy-2,9-dioxatricyclo 4,3,1,03.7 - decane esters |
| JP49014830A JPS5750793B2 (enrdf_load_stackoverflow) | 1973-02-08 | 1974-02-05 | |
| HUKA1402A HU169556B (enrdf_load_stackoverflow) | 1973-02-08 | 1974-02-05 | |
| IL44145A IL44145A (en) | 1973-02-08 | 1974-02-05 | Dioxatricyclodecanes and their production |
| AU65221/74A AU487101B2 (en) | 1973-02-08 | 1974-02-05 | 4-hydroxy 2, 0-dioxatricyclo-4, 3,1,03, 7 decanes and esters thereof with aliphatic carboxylic and carbamic acids of the general formula i |
| DD176411A DD109872A5 (enrdf_load_stackoverflow) | 1973-02-08 | 1974-02-06 | |
| CS815A CS175472B2 (enrdf_load_stackoverflow) | 1973-02-08 | 1974-02-06 | |
| NO740403A NO140981C (no) | 1973-02-08 | 1974-02-07 | Fremgangsmaate ved fremstilling av 4-alfa-hydroxy-2,9-dioxatricyclo(4,3,1,0 3,7)-decan og estere derav |
| SU7401998126A SU576939A3 (ru) | 1973-02-08 | 1974-02-07 | Способ получени карбаматов 4 -окси-2,9-диоксатрицикло-(4,3,1,0,3,7)-деканов |
| FR7404118A FR2217008B1 (enrdf_load_stackoverflow) | 1973-02-08 | 1974-02-07 | |
| AT97574*#A AT332397B (de) | 1973-02-08 | 1974-02-07 | Verfahren zur herstellung von neuen estern der 4-hydroxy-2,9-dioxatricyclo (4,3,1,03,7)decane |
| SE7401645A SE403115B (sv) | 1973-02-08 | 1974-02-07 | Sett att framstella estrar av 4-hydroxi-2,9-dioxatricyklo(4,3,1,03,7)dekaner |
| CA192,121A CA1025873A (en) | 1973-02-08 | 1974-02-08 | Derivatives of 4-hydroxy-2,9-dioxatricyclo (4.3.1.03,7)-decane and esters thereof and processes for their production |
| ZA00740845A ZA74845B (en) | 1973-02-08 | 1974-02-08 | Hydroxy-2,9-dioxa-tricyclo<4,3,10,> decanes and esters thereof |
| PH15490A PH12696A (en) | 1973-02-08 | 1974-02-08 | Esters of 4-hydroxy-2-9-dioxatricyclo-(3,1,o3,7)decanes |
| SU752109640A SU659086A3 (ru) | 1973-02-08 | 1975-03-03 | Способ получени карбаматов 4 -окси-2,9-диоксатрицикло-/4,3,1,0,3,7,/ -деканов |
| SU752121560A SU648562A1 (en) | 1973-02-08 | 1975-04-09 | 4-a-oxy-2,9-dioxatricyclo-(4,3,1,0 3,7)-decane derivatives possessing sedative hypethetic effect |
| US05/627,081 US4016176A (en) | 1973-02-08 | 1975-10-30 | Esters of 4-hydroxy-2,9-dioxatricyclo[4.3.1.03,7 ] decanes and processes for their production |
| SU762347297A SU643503A1 (ru) | 1973-02-08 | 1976-04-21 | Карбаматы 4- -гидрокси -2,9диоксатрицикло-(4,3,1,0 )деканов,про вл ющие седативно-гиппотическую активность |
| FI791977A FI58776C (fi) | 1973-02-08 | 1979-06-20 | Saett att framstaella nya 4alfa-karbamyloxi-8-alkoxi-3,10-dimetyl-2,9-dioxatricyklo-(4,3,1,03,7)-dekaner med lugnande och narkotisk verkan |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2306118A DE2306118C3 (de) | 1973-02-08 | 1973-02-08 | S-Methyl-lO-methylen^-dioxatricyclo [43,1,037I decane und 3,10-Dimethyl2,9-dioxatricyclo [43,1, 03·7! decane sowie Verfahren zu deren Herstellung |
| DE2362396A DE2362396C2 (de) | 1973-02-08 | 1973-12-15 | 3-Methyl-10-methylen-2,9-dioxatricyclo[4,3,1,0↑3↑,↑7↑] decane |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DE2306118A1 DE2306118A1 (de) | 1974-08-15 |
| DE2306118B2 DE2306118B2 (enrdf_load_stackoverflow) | 1980-02-07 |
| DE2306118C3 true DE2306118C3 (de) | 1980-10-16 |
Family
ID=32963212
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2306118A Expired DE2306118C3 (de) | 1973-02-08 | 1973-02-08 | S-Methyl-lO-methylen^-dioxatricyclo [43,1,037I decane und 3,10-Dimethyl2,9-dioxatricyclo [43,1, 03·7! decane sowie Verfahren zu deren Herstellung |
| DE2362396A Expired DE2362396C2 (de) | 1973-02-08 | 1973-12-15 | 3-Methyl-10-methylen-2,9-dioxatricyclo[4,3,1,0↑3↑,↑7↑] decane |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2362396A Expired DE2362396C2 (de) | 1973-02-08 | 1973-12-15 | 3-Methyl-10-methylen-2,9-dioxatricyclo[4,3,1,0↑3↑,↑7↑] decane |
Country Status (1)
| Country | Link |
|---|---|
| DE (2) | DE2306118C3 (enrdf_load_stackoverflow) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2607106C2 (de) | 1976-02-21 | 1986-01-16 | Kali-Chemie Pharma Gmbh, 3000 Hannover | 2,9-Dioxatricyclo[4,3,1,0↑3↑↑,↑↑7↑]decane und Verfahren zu deren Herstellung |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2730988A1 (de) | 1977-07-08 | 1979-01-25 | Kali Chemie Pharma Gmbh | 3-azidomethyl-2,9-dioxatricyclo eckige klammer auf 4,3,1,0 hoch 3,7 eckige klammer zu decane und verfahren zu deren herstellung |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1961433C3 (de) * | 1969-12-08 | 1974-06-06 | Kali Chemie Ag | S-Alkoxy^-hydroxy-S-methyl-lOmethylen-2,9-dioxatricyclo-(4,3,l,0 hoch 3,hoch 7)-decane und 8-Alkoxy-4-hydroxy-3,10-dimethyl-2,9dioxatricyclo-(4,3,1,0 hoch 3Jioch 7)-decane sowie Verfahren zu ihrer Herstellung |
-
1973
- 1973-02-08 DE DE2306118A patent/DE2306118C3/de not_active Expired
- 1973-12-15 DE DE2362396A patent/DE2362396C2/de not_active Expired
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2607106C2 (de) | 1976-02-21 | 1986-01-16 | Kali-Chemie Pharma Gmbh, 3000 Hannover | 2,9-Dioxatricyclo[4,3,1,0↑3↑↑,↑↑7↑]decane und Verfahren zu deren Herstellung |
Also Published As
| Publication number | Publication date |
|---|---|
| DE2362396C2 (de) | 1982-08-05 |
| DE2306118A1 (de) | 1974-08-15 |
| DE2362396A1 (de) | 1975-06-19 |
| DE2306118B2 (enrdf_load_stackoverflow) | 1980-02-07 |
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