DE1793315C2 - - Google Patents
Info
- Publication number
- DE1793315C2 DE1793315C2 DE1793315A DE1793315A DE1793315C2 DE 1793315 C2 DE1793315 C2 DE 1793315C2 DE 1793315 A DE1793315 A DE 1793315A DE 1793315 A DE1793315 A DE 1793315A DE 1793315 C2 DE1793315 C2 DE 1793315C2
- Authority
- DE
- Germany
- Prior art keywords
- compound
- compounds
- anesthesia
- dose
- duration
- 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
- 150000001875 compounds Chemical class 0.000 description 31
- 206010002091 Anaesthesia Diseases 0.000 description 13
- 230000037005 anaesthesia Effects 0.000 description 13
- LVTJOONKWUXEFR-FZRMHRINSA-N protoneodioscin Natural products O(C[C@@H](CC[C@]1(O)[C@H](C)[C@@H]2[C@]3(C)[C@H]([C@H]4[C@@H]([C@]5(C)C(=CC4)C[C@@H](O[C@@H]4[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@@H](O)[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@H](CO)O4)CC5)CC3)C[C@@H]2O1)C)[C@H]1[C@H](O)[C@H](O)[C@H](O)[C@@H](CO)O1 LVTJOONKWUXEFR-FZRMHRINSA-N 0.000 description 9
- 229940126062 Compound A Drugs 0.000 description 8
- NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 description 8
- 241001465754 Metazoa Species 0.000 description 8
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 6
- 230000003444 anaesthetic effect Effects 0.000 description 6
- 239000002253 acid Substances 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 4
- 230000037396 body weight Effects 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- 206010010904 Convulsion Diseases 0.000 description 3
- 241000699670 Mus sp. Species 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 238000002474 experimental method Methods 0.000 description 3
- 230000000144 pharmacologic effect Effects 0.000 description 3
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 230000036461 convulsion Effects 0.000 description 2
- NNBZCPXTIHJBJL-UHFFFAOYSA-N decalin Chemical compound C1CCCC2CCCCC21 NNBZCPXTIHJBJL-UHFFFAOYSA-N 0.000 description 2
- 238000013213 extrapolation Methods 0.000 description 2
- 239000007924 injection Substances 0.000 description 2
- 238000002347 injection Methods 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 230000003533 narcotic effect Effects 0.000 description 2
- 231100000252 nontoxic Toxicity 0.000 description 2
- 230000003000 nontoxic effect Effects 0.000 description 2
- 239000002504 physiological saline solution Substances 0.000 description 2
- 230000008707 rearrangement Effects 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
- 231100000419 toxicity Toxicity 0.000 description 2
- 230000001988 toxicity Effects 0.000 description 2
- IXDGGSSUYSFGOK-UHFFFAOYSA-N 2-amino-2-phenylcyclohexan-1-one Chemical compound C=1C=CC=CC=1C1(N)CCCCC1=O IXDGGSSUYSFGOK-UHFFFAOYSA-N 0.000 description 1
- 125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 description 1
- KICREDOLXPKCLZ-UHFFFAOYSA-N 2-hydroxy-2-phenylcycloheptan-1-one Chemical compound C=1C=CC=CC=1C1(O)CCCCCC1=O KICREDOLXPKCLZ-UHFFFAOYSA-N 0.000 description 1
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
- RUHCRRZVUZYFAQ-UHFFFAOYSA-N CNC1(CCCC1)C1=CC=CC(C(C(C=CC=C2C3(CCCC3)NC)=C2Cl)=O)=C1Cl Chemical compound CNC1(CCCC1)C1=CC=CC(C(C(C=CC=C2C3(CCCC3)NC)=C2Cl)=O)=C1Cl RUHCRRZVUZYFAQ-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- 241000282693 Cercopithecidae Species 0.000 description 1
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
- 206010021118 Hypotonia Diseases 0.000 description 1
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 1
- 108010021119 Trichosanthin Proteins 0.000 description 1
- 208000003443 Unconsciousness Diseases 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 229940035674 anesthetics Drugs 0.000 description 1
- 230000002903 catalepsic effect Effects 0.000 description 1
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexyloxide Natural products O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 1
- 239000003193 general anesthetic agent Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- 150000002466 imines Chemical class 0.000 description 1
- 230000001939 inductive effect Effects 0.000 description 1
- 231100000636 lethal dose Toxicity 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 210000003205 muscle Anatomy 0.000 description 1
- 230000036640 muscle relaxation Effects 0.000 description 1
- 230000003040 nociceptive effect Effects 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000004904 shortening Methods 0.000 description 1
- CDBYLPFSWZWCQE-UHFFFAOYSA-L sodium carbonate Substances [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 230000002747 voluntary effect Effects 0.000 description 1
- 230000002618 waking effect Effects 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
- PICXIOQBANWBIZ-UHFFFAOYSA-N zinc;1-oxidopyridine-2-thione Chemical class [Zn+2].[O-]N1C=CC=CC1=S.[O-]N1C=CC=CC1=S PICXIOQBANWBIZ-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/13—Amines
- A61K31/135—Amines having aromatic rings, e.g. ketamine, nortriptyline
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/13—Amines
-
- 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
- C07C45/51—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by pyrolysis, rearrangement or decomposition
- C07C45/54—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by pyrolysis, rearrangement or decomposition of compounds containing doubly bound oxygen atoms, e.g. esters
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D303/00—Compounds containing three-membered rings having one oxygen atom as the only ring hetero atom
- C07D303/02—Compounds containing oxirane rings
- C07D303/48—Compounds containing oxirane rings with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms, e.g. ester or nitrile radicals
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (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)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US206188A US3254124A (en) | 1962-06-29 | 1962-06-29 | Aminoketones and methods for their production |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE1793315B1 DE1793315B1 (de) | 1972-05-25 |
| DE1793315C2 true DE1793315C2 (enExample) | 1973-01-04 |
Family
ID=22765332
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEST20790A Pending DE1293761B (de) | 1962-06-29 | 1963-06-28 | Verfahren zur Herstellung von Aminoketonen |
| DE19631793315 Granted DE1793315B1 (de) | 1962-06-29 | 1963-06-28 | 2-Methylamino-2-(o-chlorphenyl)-cyclohexanon und seine pharmakologisch vertraeglichen Saeureadditionsverbindungen |
Family Applications Before (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEST20790A Pending DE1293761B (de) | 1962-06-29 | 1963-06-28 | Verfahren zur Herstellung von Aminoketonen |
Country Status (4)
| Country | Link |
|---|---|
| US (1) | US3254124A (enExample) |
| BR (1) | BR6350196D0 (enExample) |
| DE (2) | DE1293761B (enExample) |
| FR (1) | FR2973M (enExample) |
Families Citing this family (30)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3394182A (en) * | 1962-06-29 | 1968-07-23 | Parke Davis & Co | Alpha-hydroxyimines and methods for their production |
| DE1242241B (de) * | 1964-04-08 | 1967-06-15 | Boehringer Sohn Ingelheim | Verfahren zur Herstellung von substituierten Phenyl-alpha-aminoketonen und deren Saeureadditionssalzen bzw. deren optischen Antipoden |
| US3522273A (en) * | 1965-03-19 | 1970-07-28 | Parke Davis & Co | 2-(ethylamino)-2-(2-thienyl)cyclohexanone and acid addition salts |
| US3361817A (en) * | 1965-07-30 | 1968-01-02 | Parke Davis & Co | 2-(alkoxyalkyl)amino-2-phenyl-cyclohexanones and salts thereof |
| US3542869A (en) * | 1967-10-25 | 1970-11-24 | Bristol Myers Co | 1-amino-1-(o-chlorophenyl)-2-butanone and the acid salts thereof |
| US3494964A (en) * | 1969-01-13 | 1970-02-10 | Lilly Co Eli | Alpha-halo-alpha-amino ketones |
| DE3541181A1 (de) * | 1985-11-21 | 1987-05-27 | Basf Ag | Propylamine, verfahren zu ihrer herstellung und ihre verwendung als fungizide |
| US5250732A (en) * | 1991-07-18 | 1993-10-05 | Genentech, Inc. | Ketamine analogues for treatment of thrombocytopenia |
| DE4409671C1 (de) * | 1994-03-15 | 1995-03-23 | Detlef Dr Preiss | Verwendung von 2-Methylamino-2-phenylcyclohexanon zur Behandlung von Bakterien-, Pilz-, Virus-, oder Protozoeninfektionen und zur Immunmodulation |
| US6197830B1 (en) | 1995-09-22 | 2001-03-06 | Bruce M. Frome | Method for achieving relief from sympathetically mediated pain |
| DE10025946A1 (de) * | 2000-05-26 | 2001-11-29 | Gruenenthal Gmbh | Wirkstoffkombination |
| US20040082543A1 (en) * | 2002-10-29 | 2004-04-29 | Pharmacia Corporation | Compositions of cyclooxygenase-2 selective inhibitors and NMDA receptor antagonists for the treatment or prevention of neuropathic pain |
| US8268866B2 (en) * | 2004-03-29 | 2012-09-18 | Matthieu Guitton | Methods for the treatment of tinnitus induced by cochlear excitotoxicity |
| US9072662B2 (en) | 2004-03-29 | 2015-07-07 | Auris Medical Ag | Methods for the treatment of tinnitus induced by cochlear excitotoxicity |
| US20060063802A1 (en) * | 2004-03-29 | 2006-03-23 | Matthieu Guitton | Methods for the treatment of tinnitus induced by cochlear excitotoxicity |
| DE102005004343A1 (de) * | 2005-01-25 | 2006-08-10 | Eberhard-Karls-Universität Tübingen Universitätsklinikum | Behandlung von Phantomphänomenen |
| KR101271263B1 (ko) | 2005-09-28 | 2013-06-07 | 아우리스 메디칼 아게 | 내이 장애 치료용 약학 조성물 |
| JP5941159B2 (ja) | 2011-12-12 | 2016-06-29 | オトラーヌム アーゲー | 聴覚系における塩素イオン共輸送体ｎｋｃｃ１の調節による耳鳴の治療 |
| EP2903963A4 (en) | 2012-10-08 | 2016-05-25 | Auckland Uniservices Ltd | KETAMINE DERIVATIVES |
| EP3964203A1 (en) | 2013-09-13 | 2022-03-09 | National University Corporation Chiba University | Application of r-ketamine and salt thereof as pharmaceuticals |
| WO2017087691A1 (en) | 2015-11-17 | 2017-05-26 | The Trustees Of Columbia University In The City Of New York | Pharmacological prophylactics against stress-induced affective disorders and their associated symptoms |
| EP3383429B1 (en) | 2015-11-30 | 2020-10-14 | INSERM - Institut National de la Santé et de la Recherche Médicale | Nmdar antagonists for the treatment of tumor angiogenesis |
| AU2017250086A1 (en) | 2016-04-11 | 2018-09-20 | Clexio Biosciences Ltd. | Deuterated ketamine derivatives |
| WO2019094596A1 (en) | 2017-11-09 | 2019-05-16 | The Trustees Of Columbia University In The City Of New York | Biomarkers for efficacy of prophylactic treatments against stress-induced affective disorders |
| WO2019094757A1 (en) | 2017-11-09 | 2019-05-16 | The Trustees Of Columbia University In The City Of New York | Pharmacological prophylactics against stress-induced affective disorders in females |
| EP3505509A1 (en) | 2017-12-29 | 2019-07-03 | Université de Liège | Methods for the preparation of arylcycloalkylamine derivatives |
| CN118453559A (zh) | 2018-02-15 | 2024-08-09 | 国立大学法人千叶大学 | 炎症性疾病或骨病的预防或治疗剂及医药组合物 |
| CN112533595A (zh) | 2018-05-04 | 2021-03-19 | 感知神经科学公司 | 治疗物质滥用的方法 |
| CN110540510B (zh) * | 2019-05-24 | 2020-08-07 | 北京大学深圳研究生院 | 一种长效化合物的制备方法 |
| WO2022208144A1 (en) * | 2021-03-31 | 2022-10-06 | Supriya Lifescience Ltd | A crystalline form of 2-(2-chlorophenyl)-2-(methylamino) cyclohexanone hydrochloride and method thereof |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB853775A (en) * | 1957-09-19 | 1960-11-09 | Parke Davis & Co | Pharmaceutical compositions and methods for producing phenylcyclohexane compounds |
| US3068236A (en) * | 1960-10-17 | 1962-12-11 | Olin Mathieson | N-(2-imino-2-phenylethyl)amines and a process for their preparation |
| DE1159431B (de) * | 1961-08-18 | 1963-12-19 | Boehringer Sohn Ingelheim | Verfahren zur Herstellung von 1-Cyclohexyl-2-amino-propanon-(1) und dessen Salzen |
-
1962
- 1962-06-29 US US206188A patent/US3254124A/en not_active Expired - Lifetime
-
1963
- 1963-06-26 BR BR150196/63A patent/BR6350196D0/pt unknown
- 1963-06-28 DE DEST20790A patent/DE1293761B/de active Pending
- 1963-06-28 DE DE19631793315 patent/DE1793315B1/de active Granted
- 1963-08-13 FR FR944543A patent/FR2973M/fr not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| US3254124A (en) | 1966-05-31 |
| BR6350196D0 (pt) | 1973-04-26 |
| DE1793315B1 (de) | 1972-05-25 |
| FR2973M (fr) | 1964-11-30 |
| DE1293761B (de) | 1969-04-30 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| E77 | Valid patent as to the heymanns-index 1977 |