DE1518959B1 - Verfahren zur Herstellung von basisch substituierten Cyclohexenen - Google Patents
Verfahren zur Herstellung von basisch substituierten CyclohexenenInfo
- Publication number
- DE1518959B1 DE1518959B1 DE19651518959 DE1518959A DE1518959B1 DE 1518959 B1 DE1518959 B1 DE 1518959B1 DE 19651518959 DE19651518959 DE 19651518959 DE 1518959 A DE1518959 A DE 1518959A DE 1518959 B1 DE1518959 B1 DE 1518959B1
- Authority
- DE
- Germany
- Prior art keywords
- dolantin
- intragastric
- general formula
- phenyl
- animals
- 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.)
- Pending
Links
- 238000000034 method Methods 0.000 title claims description 7
- 150000001935 cyclohexenes Chemical class 0.000 title claims description 4
- 238000002360 preparation method Methods 0.000 title description 3
- -1 atropic acid ester Chemical class 0.000 claims description 6
- 239000002904 solvent Substances 0.000 claims description 5
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
- 125000000623 heterocyclic group Chemical group 0.000 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 2
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 2
- XADCESSVHJOZHK-UHFFFAOYSA-N Meperidine Chemical compound C=1C=CC=CC=1C1(C(=O)OCC)CCN(C)CC1 XADCESSVHJOZHK-UHFFFAOYSA-N 0.000 description 26
- 241001465754 Metazoa Species 0.000 description 15
- 239000000126 substance Substances 0.000 description 10
- 238000006243 chemical reaction Methods 0.000 description 9
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 8
- 150000001875 compounds Chemical class 0.000 description 8
- 230000000694 effects Effects 0.000 description 8
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 7
- 238000012360 testing method Methods 0.000 description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- 230000015572 biosynthetic process Effects 0.000 description 6
- 210000000936 intestine Anatomy 0.000 description 6
- 238000007920 subcutaneous administration Methods 0.000 description 6
- 241000699670 Mus sp. Species 0.000 description 5
- 150000001993 dienes Chemical class 0.000 description 5
- 231100000419 toxicity Toxicity 0.000 description 5
- 230000001988 toxicity Effects 0.000 description 5
- 238000005303 weighing Methods 0.000 description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- 230000000202 analgesic effect Effects 0.000 description 4
- 229940035676 analgesics Drugs 0.000 description 4
- 239000000730 antalgic agent Substances 0.000 description 4
- 238000009395 breeding Methods 0.000 description 4
- 230000001488 breeding effect Effects 0.000 description 4
- HGCIXCUEYOPUTN-UHFFFAOYSA-N cyclohexene Chemical compound C1CCC=CC1 HGCIXCUEYOPUTN-UHFFFAOYSA-N 0.000 description 4
- 238000005259 measurement Methods 0.000 description 4
- BQJCRHHNABKAKU-KBQPJGBKSA-N morphine Chemical compound O([C@H]1[C@H](C=C[C@H]23)O)C4=C5[C@@]12CCN(C)[C@@H]3CC5=CC=C4O BQJCRHHNABKAKU-KBQPJGBKSA-N 0.000 description 4
- 239000011780 sodium chloride Substances 0.000 description 4
- 238000003786 synthesis reaction Methods 0.000 description 4
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 3
- ONPJWQSDZCGSQM-UHFFFAOYSA-N 2-phenylprop-2-enoic acid Chemical class OC(=O)C(=C)C1=CC=CC=C1 ONPJWQSDZCGSQM-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 238000010171 animal model Methods 0.000 description 3
- 229940125904 compound 1 Drugs 0.000 description 3
- APTSVSMRHNVGNE-UHFFFAOYSA-N cyclohexene;hydrochloride Chemical compound Cl.C1CCC=CC1 APTSVSMRHNVGNE-UHFFFAOYSA-N 0.000 description 3
- 238000002474 experimental method Methods 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 238000000926 separation method Methods 0.000 description 3
- 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 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- 238000011785 NMRI mouse Methods 0.000 description 2
- 241000700159 Rattus Species 0.000 description 2
- 208000004756 Respiratory Insufficiency Diseases 0.000 description 2
- 206010038678 Respiratory depression Diseases 0.000 description 2
- BUNYBPVXEKRSGY-UHFFFAOYSA-N buta-1,3-dien-1-amine Chemical class NC=CC=C BUNYBPVXEKRSGY-UHFFFAOYSA-N 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 239000003651 drinking water Substances 0.000 description 2
- 235000020188 drinking water Nutrition 0.000 description 2
- BOIWYTYYWPXGAT-UHFFFAOYSA-N ethyl 2-phenylprop-2-enoate Chemical compound CCOC(=O)C(=C)C1=CC=CC=C1 BOIWYTYYWPXGAT-UHFFFAOYSA-N 0.000 description 2
- 238000001640 fractional crystallisation Methods 0.000 description 2
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 2
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 2
- 238000002955 isolation Methods 0.000 description 2
- 229960005181 morphine Drugs 0.000 description 2
- 230000036407 pain Effects 0.000 description 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
- 230000000241 respiratory effect Effects 0.000 description 2
- 230000029058 respiratory gaseous exchange Effects 0.000 description 2
- 235000000891 standard diet Nutrition 0.000 description 2
- 229910018072 Al 2 O 3 Inorganic materials 0.000 description 1
- 206010002091 Anaesthesia Diseases 0.000 description 1
- 241000700198 Cavia Species 0.000 description 1
- 241000700199 Cavia porcellus Species 0.000 description 1
- 238000005698 Diels-Alder reaction Methods 0.000 description 1
- 241000282326 Felis catus Species 0.000 description 1
- 239000004425 Makrolon Substances 0.000 description 1
- 241000906446 Theraps Species 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 230000003213 activating effect Effects 0.000 description 1
- 230000007059 acute toxicity Effects 0.000 description 1
- 231100000403 acute toxicity Toxicity 0.000 description 1
- 230000037005 anaesthesia Effects 0.000 description 1
- UORJNBVJVRLXMQ-UHFFFAOYSA-N aprobarbital Chemical compound C=CCC1(C(C)C)C(=O)NC(=O)NC1=O UORJNBVJVRLXMQ-UHFFFAOYSA-N 0.000 description 1
- 235000021028 berry Nutrition 0.000 description 1
- OBAMWENTFIOOIT-UHFFFAOYSA-N butan-2-one;ethyl acetate Chemical compound CCC(C)=O.CCOC(C)=O OBAMWENTFIOOIT-UHFFFAOYSA-N 0.000 description 1
- 150000001733 carboxylic acid esters Chemical class 0.000 description 1
- 229940126214 compound 3 Drugs 0.000 description 1
- 230000008602 contraction Effects 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 230000007123 defense Effects 0.000 description 1
- 230000003001 depressive effect Effects 0.000 description 1
- 230000000994 depressogenic effect Effects 0.000 description 1
- 239000003517 fume Substances 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 230000002496 gastric effect Effects 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 230000000968 intestinal effect Effects 0.000 description 1
- 238000001990 intravenous administration Methods 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- 231100001231 less toxic Toxicity 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 231100000053 low toxicity Toxicity 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- HUNXXGIRNGEBFU-UHFFFAOYSA-N n,n-diethylbuta-1,3-dien-1-amine Chemical compound CCN(CC)C=CC=C HUNXXGIRNGEBFU-UHFFFAOYSA-N 0.000 description 1
- 238000006053 organic reaction Methods 0.000 description 1
- AZQWKYJCGOJGHM-UHFFFAOYSA-N para-benzoquinone Natural products O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 description 1
- 230000008855 peristalsis Effects 0.000 description 1
- WCNLCIJMFAJCPX-UHFFFAOYSA-N pethidine hydrochloride Chemical compound Cl.C=1C=CC=CC=1C1(C(=O)OCC)CCN(C)CC1 WCNLCIJMFAJCPX-UHFFFAOYSA-N 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 229920000515 polycarbonate Polymers 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 230000002250 progressing effect Effects 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000012552 review Methods 0.000 description 1
- 239000011877 solvent mixture Substances 0.000 description 1
- 239000004071 soot Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 230000001629 suppression Effects 0.000 description 1
- 231100000041 toxicology testing Toxicity 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/21—Cyclic compounds having at least one ring containing silicon, but no carbon in the ring
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Debarking, Splitting, And Disintegration Of Timber (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEG0045235 | 1965-11-19 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1518959B1 true DE1518959B1 (de) | 1970-03-26 |
Family
ID=7127679
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19651518959 Pending DE1518959B1 (de) | 1965-11-19 | 1965-11-19 | Verfahren zur Herstellung von basisch substituierten Cyclohexenen |
Country Status (9)
| Country | Link |
|---|---|
| BE (1) | BE689848A (enrdf_load_stackoverflow) |
| BR (1) | BR6684690D0 (enrdf_load_stackoverflow) |
| CH (1) | CH468351A (enrdf_load_stackoverflow) |
| DE (1) | DE1518959B1 (enrdf_load_stackoverflow) |
| DK (1) | DK129196B (enrdf_load_stackoverflow) |
| GB (1) | GB1120186A (enrdf_load_stackoverflow) |
| NL (1) | NL148876B (enrdf_load_stackoverflow) |
| NO (1) | NO119837B (enrdf_load_stackoverflow) |
| SE (1) | SE332632B (enrdf_load_stackoverflow) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1999003821A3 (en) * | 1997-07-14 | 1999-05-20 | Russinsky Ltd | Process for isomerisation of tilidine |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1216152A (en) * | 1968-05-08 | 1970-12-16 | Warner Lambert Pharmaceutical | Derivatives of cyclohexene |
| US4028398A (en) * | 1970-02-17 | 1977-06-07 | Warner-Lambert Company | Process for substituted cyclohexenes and its products |
| DE2107871B2 (de) * | 1971-02-18 | 1973-07-19 | 1-phenyl-4-amino-cyclohex-2-en-1 carbonsaeureester, verfahren zu deren herstellung und diese enthaltende analgetisch wirksame arzneimittel | |
| IE990300A1 (en) * | 1998-04-28 | 2000-05-17 | Russinsky Ltd | Tilidine Embonate |
| GB2339570B (en) * | 1998-07-14 | 2003-04-16 | Russinsky Ltd | Tilidine salts |
-
1965
- 1965-11-19 DE DE19651518959 patent/DE1518959B1/de active Pending
-
1966
- 1966-10-27 GB GB4832266A patent/GB1120186A/en not_active Expired
- 1966-11-16 NO NO16560266A patent/NO119837B/no unknown
- 1966-11-17 BE BE689848D patent/BE689848A/xx not_active IP Right Cessation
- 1966-11-17 NL NL6616226A patent/NL148876B/xx not_active IP Right Cessation
- 1966-11-18 SE SE1584266A patent/SE332632B/xx unknown
- 1966-11-18 DK DK598766A patent/DK129196B/da not_active IP Right Cessation
- 1966-11-18 CH CH1656466A patent/CH468351A/fr unknown
- 1966-11-18 BR BR18469066A patent/BR6684690D0/pt unknown
Non-Patent Citations (1)
| Title |
|---|
| None * |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1999003821A3 (en) * | 1997-07-14 | 1999-05-20 | Russinsky Ltd | Process for isomerisation of tilidine |
Also Published As
| Publication number | Publication date |
|---|---|
| NL6616226A (enrdf_load_stackoverflow) | 1967-05-22 |
| CH468351A (fr) | 1969-02-15 |
| DK129196B (da) | 1974-09-09 |
| DK129196C (enrdf_load_stackoverflow) | 1975-01-27 |
| BE689848A (enrdf_load_stackoverflow) | 1967-05-17 |
| NO119837B (enrdf_load_stackoverflow) | 1970-07-13 |
| NL148876B (nl) | 1976-03-15 |
| GB1120186A (en) | 1968-07-17 |
| BR6684690D0 (pt) | 1973-12-18 |
| SE332632B (enrdf_load_stackoverflow) | 1971-02-15 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| E77 | Valid patent as to the heymanns-index 1977 |