DE1245937B - - Google Patents
Info
- Publication number
- DE1245937B DE1245937B DENDAT1245937D DE1245937DA DE1245937B DE 1245937 B DE1245937 B DE 1245937B DE NDAT1245937 D DENDAT1245937 D DE NDAT1245937D DE 1245937D A DE1245937D A DE 1245937DA DE 1245937 B DE1245937 B DE 1245937B
- Authority
- DE
- Germany
- Prior art keywords
- corneal
- compounds
- viii
- lidocaine hydrochloride
- values
- 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
- 150000001875 compounds Chemical class 0.000 claims description 16
- 238000000034 method Methods 0.000 claims description 11
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 8
- 150000003839 salts Chemical class 0.000 claims description 5
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- 230000003444 anaesthetic effect Effects 0.000 claims description 4
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 4
- 231100000419 toxicity Toxicity 0.000 claims description 4
- 230000001988 toxicity Effects 0.000 claims description 4
- 230000000694 effects Effects 0.000 claims description 3
- 239000003589 local anesthetic agent Substances 0.000 claims description 3
- 239000000243 solution Substances 0.000 claims description 3
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 2
- NNJVILVZKWQKPM-UHFFFAOYSA-N Lidocaine Chemical compound CCN(CC)CC(=O)NC1=C(C)C=CC=C1C NNJVILVZKWQKPM-UHFFFAOYSA-N 0.000 claims description 2
- 239000002253 acid Substances 0.000 claims description 2
- 150000007513 acids Chemical class 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims description 2
- 229960004194 lidocaine Drugs 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- 238000002360 preparation method Methods 0.000 claims description 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 2
- 229960004393 lidocaine hydrochloride Drugs 0.000 claims 6
- YECIFGHRMFEPJK-UHFFFAOYSA-N lidocaine hydrochloride monohydrate Chemical compound O.[Cl-].CC[NH+](CC)CC(=O)NC1=C(C)C=CC=C1C YECIFGHRMFEPJK-UHFFFAOYSA-N 0.000 claims 6
- FKLJPTJMIBLJAV-UHFFFAOYSA-N Compound IV Chemical compound O1N=C(C)C=C1CCCCCCCOC1=CC=C(C=2OCCN=2)C=C1 FKLJPTJMIBLJAV-UHFFFAOYSA-N 0.000 claims 1
- 241001465754 Metazoa Species 0.000 claims 1
- 239000000443 aerosol Substances 0.000 claims 1
- 238000001990 intravenous administration Methods 0.000 claims 1
- 231100001231 less toxic Toxicity 0.000 claims 1
- 239000002674 ointment Substances 0.000 claims 1
- 239000008177 pharmaceutical agent Substances 0.000 claims 1
- 231100000916 relative toxicity Toxicity 0.000 claims 1
- 239000007921 spray Substances 0.000 claims 1
- 231100000331 toxic Toxicity 0.000 claims 1
- 230000002588 toxic effect Effects 0.000 claims 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 30
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 13
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 13
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 11
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- 239000000203 mixture Substances 0.000 description 6
- FRXJYUFHAXXSAL-UHFFFAOYSA-N 3-chloro-n-phenylpropanamide Chemical compound ClCCC(=O)NC1=CC=CC=C1 FRXJYUFHAXXSAL-UHFFFAOYSA-N 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- 238000002844 melting Methods 0.000 description 4
- 230000008018 melting Effects 0.000 description 4
- LHHACTKLABTCQF-UHFFFAOYSA-N [amino(hydroxy)methylidene]-methylazanium;chloride Chemical compound Cl.CNC(O)=N LHHACTKLABTCQF-UHFFFAOYSA-N 0.000 description 3
- -1 o -Trifluoromethylphenylcarbamoyl Chemical group 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- 241000700199 Cavia porcellus Species 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- GMEGXJPUFRVCPX-UHFFFAOYSA-N butylthiourea Chemical compound CCCCNC(N)=S GMEGXJPUFRVCPX-UHFFFAOYSA-N 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- HIXDQWDOVZUNNA-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-hydroxy-7-methoxychromen-4-one Chemical compound C=1C(OC)=CC(O)=C(C(C=2)=O)C=1OC=2C1=CC=C(OC)C(OC)=C1 HIXDQWDOVZUNNA-UHFFFAOYSA-N 0.000 description 1
- GOWBOXSTKDXKSK-UHFFFAOYSA-N 3-chloro-n-(2-methylphenyl)propanamide Chemical compound CC1=CC=CC=C1NC(=O)CCCl GOWBOXSTKDXKSK-UHFFFAOYSA-N 0.000 description 1
- XTAFQSKBUBILAB-UHFFFAOYSA-N 3-chloro-n-[2-(trifluoromethyl)phenyl]propanamide Chemical compound FC(F)(F)C1=CC=CC=C1NC(=O)CCCl XTAFQSKBUBILAB-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- 241000699670 Mus sp. Species 0.000 description 1
- 241000906446 Theraps Species 0.000 description 1
- 208000024780 Urticaria Diseases 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 210000004087 cornea Anatomy 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- LEEHHPPLIOFGSC-UHFFFAOYSA-N cyclohexylthiourea Chemical compound NC(=S)NC1CCCCC1 LEEHHPPLIOFGSC-UHFFFAOYSA-N 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 239000012458 free base Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 238000010253 intravenous injection Methods 0.000 description 1
- 150000002541 isothioureas Chemical class 0.000 description 1
- 231100000518 lethal Toxicity 0.000 description 1
- 230000001665 lethal effect Effects 0.000 description 1
- 229960005015 local anesthetics Drugs 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 150000003585 thioureas Chemical class 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C335/00—Thioureas, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups
- C07C335/30—Isothioureas
- C07C335/32—Isothioureas having sulfur atoms of isothiourea groups bound to acyclic carbon atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US39528664A | 1964-09-09 | 1964-09-09 | |
| US639609A US3407229A (en) | 1964-09-09 | 1967-05-19 | Phenylcarbamoylethylthiopseudoureas |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1245937B true DE1245937B (enExample) | 1967-08-03 |
Family
ID=27015052
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DENDAT1245937D Pending DE1245937B (enExample) | 1964-09-09 |
Country Status (4)
| Country | Link |
|---|---|
| US (1) | US3407229A (enExample) |
| BE (1) | BE667452A (enExample) |
| DE (1) | DE1245937B (enExample) |
| GB (1) | GB1089284A (enExample) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RU2354647C2 (ru) * | 2007-06-28 | 2009-05-10 | Общество С Ограниченной Ответственностью "Бионика" | Новые соединения, обладающие функцией ингибиторов тромбина, и фармацевтические композиции на их основе |
| RU2353619C2 (ru) * | 2007-06-28 | 2009-04-27 | Общество С Ограниченной Ответственностью "Бионика" | Новые соединения, обладающие функцией антикоагулянтов, фармацевтические композиции на их основе для лечения тромботических состояний и плазмозамещающий раствор для коррекции гиперкоагуляционных нарушений при гемодилюции |
-
0
- DE DENDAT1245937D patent/DE1245937B/de active Pending
-
1965
- 1965-07-13 GB GB29574/65A patent/GB1089284A/en not_active Expired
- 1965-07-27 BE BE667452D patent/BE667452A/xx unknown
-
1967
- 1967-05-19 US US639609A patent/US3407229A/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| GB1089284A (en) | 1967-11-01 |
| BE667452A (enExample) | 1965-11-16 |
| US3407229A (en) | 1968-10-22 |
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