DE2166355C2 - Verwendung von d,1-Sobrerol bei der Balsamtherapie der Atemwege - Google Patents
Verwendung von d,1-Sobrerol bei der Balsamtherapie der AtemwegeInfo
- Publication number
- DE2166355C2 DE2166355C2 DE2166355A DE2166355A DE2166355C2 DE 2166355 C2 DE2166355 C2 DE 2166355C2 DE 2166355 A DE2166355 A DE 2166355A DE 2166355 A DE2166355 A DE 2166355A DE 2166355 C2 DE2166355 C2 DE 2166355C2
- Authority
- DE
- Germany
- Prior art keywords
- sobrerol
- therapy
- balm
- respiratory tract
- expectoration
- 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
- 229960000230 sobrerol Drugs 0.000 title claims description 45
- 238000002560 therapeutic procedure Methods 0.000 title claims description 7
- 235000010654 Melissa officinalis Nutrition 0.000 title claims description 6
- 239000000865 liniment Substances 0.000 title claims description 6
- 241000021559 Dicerandra Species 0.000 title claims 2
- 210000002345 respiratory system Anatomy 0.000 title description 5
- OMDMTHRBGUBUCO-IUCAKERBSA-N (1s,5s)-5-(2-hydroxypropan-2-yl)-2-methylcyclohex-2-en-1-ol Chemical compound CC1=CC[C@H](C(C)(C)O)C[C@@H]1O OMDMTHRBGUBUCO-IUCAKERBSA-N 0.000 claims description 31
- OMDMTHRBGUBUCO-UHFFFAOYSA-N trans-sobrerol Natural products CC1=CCC(C(C)(C)O)CC1O OMDMTHRBGUBUCO-UHFFFAOYSA-N 0.000 claims description 15
- 150000001875 compounds Chemical class 0.000 claims description 5
- 238000002844 melting Methods 0.000 claims description 5
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- NQFUSWIGRKFAHK-UHFFFAOYSA-N 2,3-epoxypinane Chemical compound CC12OC1CC1C(C)(C)C2C1 NQFUSWIGRKFAHK-UHFFFAOYSA-N 0.000 claims 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 15
- 230000000694 effects Effects 0.000 description 14
- 206010036790 Productive cough Diseases 0.000 description 11
- 238000002347 injection Methods 0.000 description 11
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- 206010006451 bronchitis Diseases 0.000 description 10
- ADVGKWPZRIDURE-UHFFFAOYSA-N 2'-Hydroxyacetanilide Chemical compound CC(=O)NC1=CC=CC=C1O ADVGKWPZRIDURE-UHFFFAOYSA-N 0.000 description 9
- 239000000047 product Substances 0.000 description 9
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- 208000007451 chronic bronchitis Diseases 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- 244000062730 Melissa officinalis Species 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
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- LBOPECYONBDFEM-LREBCSMRSA-N (2r,3r)-2,3-dihydroxybutanedioic acid;4-[1-hydroxy-2-(propan-2-ylamino)ethyl]benzene-1,2-diol Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O.CC(C)NCC(O)C1=CC=C(O)C(O)=C1 LBOPECYONBDFEM-LREBCSMRSA-N 0.000 description 3
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- XMEVHPAGJVLHIG-FMZCEJRJSA-N chembl454950 Chemical compound [Cl-].C1=CC=C2[C@](O)(C)[C@H]3C[C@H]4[C@H]([NH+](C)C)C(O)=C(C(N)=O)C(=O)[C@@]4(O)C(O)=C3C(=O)C2=C1O XMEVHPAGJVLHIG-FMZCEJRJSA-N 0.000 description 3
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- 229960004989 tetracycline hydrochloride Drugs 0.000 description 3
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- 206010014561 Emphysema Diseases 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 2
- TWRXJAOTZQYOKJ-UHFFFAOYSA-L Magnesium chloride Chemical compound [Mg+2].[Cl-].[Cl-] TWRXJAOTZQYOKJ-UHFFFAOYSA-L 0.000 description 2
- 241000699670 Mus sp. Species 0.000 description 2
- 241000700159 Rattus Species 0.000 description 2
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- 235000019359 magnesium stearate Nutrition 0.000 description 2
- 235000010270 methyl p-hydroxybenzoate Nutrition 0.000 description 2
- 239000004292 methyl p-hydroxybenzoate Substances 0.000 description 2
- LXCFILQKKLGQFO-UHFFFAOYSA-N methylparaben Chemical compound COC(=O)C1=CC=C(O)C=C1 LXCFILQKKLGQFO-UHFFFAOYSA-N 0.000 description 2
- 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 2
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- WXMKPNITSTVMEF-UHFFFAOYSA-M sodium benzoate Chemical compound [Na+].[O-]C(=O)C1=CC=CC=C1 WXMKPNITSTVMEF-UHFFFAOYSA-M 0.000 description 2
- 235000010234 sodium benzoate Nutrition 0.000 description 2
- 239000004299 sodium benzoate Substances 0.000 description 2
- HRZFUMHJMZEROT-UHFFFAOYSA-L sodium disulfite Chemical compound [Na+].[Na+].[O-]S(=O)S([O-])(=O)=O HRZFUMHJMZEROT-UHFFFAOYSA-L 0.000 description 2
- 235000010262 sodium metabisulphite Nutrition 0.000 description 2
- 230000004936 stimulating effect Effects 0.000 description 2
- UCSJYZPVAKXKNQ-HZYVHMACSA-N streptomycin Chemical compound CN[C@H]1[C@H](O)[C@@H](O)[C@H](CO)O[C@H]1O[C@@H]1[C@](C=O)(O)[C@H](C)O[C@H]1O[C@@H]1[C@@H](NC(N)=N)[C@H](O)[C@@H](NC(N)=N)[C@H](O)[C@H]1O UCSJYZPVAKXKNQ-HZYVHMACSA-N 0.000 description 2
- 239000004094 surface-active agent Substances 0.000 description 2
- 150000003505 terpenes Chemical class 0.000 description 2
- 235000007586 terpenes Nutrition 0.000 description 2
- 230000001225 therapeutic effect Effects 0.000 description 2
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- NQFUSWIGRKFAHK-KEMUHUQJSA-N α-pinene-oxide Chemical compound CC12OC1C[C@H]1C(C)(C)[C@@H]2C1 NQFUSWIGRKFAHK-KEMUHUQJSA-N 0.000 description 2
- NOOLISFMXDJSKH-UTLUCORTSA-N (+)-Neomenthol Chemical compound CC(C)[C@@H]1CC[C@@H](C)C[C@@H]1O NOOLISFMXDJSKH-UTLUCORTSA-N 0.000 description 1
- DTGKSKDOIYIVQL-WEDXCCLWSA-N (+)-borneol Chemical group C1C[C@@]2(C)[C@@H](O)C[C@@H]1C2(C)C DTGKSKDOIYIVQL-WEDXCCLWSA-N 0.000 description 1
- WTARULDDTDQWMU-RKDXNWHRSA-N (+)-β-pinene Chemical compound C1[C@H]2C(C)(C)[C@@H]1CCC2=C WTARULDDTDQWMU-RKDXNWHRSA-N 0.000 description 1
- JWZZKOKVBUJMES-UHFFFAOYSA-N (+-)-Isoprenaline Chemical compound CC(C)NCC(O)C1=CC=C(O)C(O)=C1 JWZZKOKVBUJMES-UHFFFAOYSA-N 0.000 description 1
- WTARULDDTDQWMU-IUCAKERBSA-N (-)-Nopinene Natural products C1[C@@H]2C(C)(C)[C@H]1CCC2=C WTARULDDTDQWMU-IUCAKERBSA-N 0.000 description 1
- GRWFGVWFFZKLTI-IUCAKERBSA-N (-)-α-pinene Chemical compound CC1=CC[C@@H]2C(C)(C)[C@H]1C2 GRWFGVWFFZKLTI-IUCAKERBSA-N 0.000 description 1
- DYWNLSQWJMTVGJ-UHFFFAOYSA-N (1-hydroxy-1-phenylpropan-2-yl)azanium;chloride Chemical compound Cl.CC(N)C(O)C1=CC=CC=C1 DYWNLSQWJMTVGJ-UHFFFAOYSA-N 0.000 description 1
- YQSHYGCCYVPRDI-UHFFFAOYSA-N (4-propan-2-ylphenyl)methanamine Chemical compound CC(C)C1=CC=C(CN)C=C1 YQSHYGCCYVPRDI-UHFFFAOYSA-N 0.000 description 1
- PHXCSXYIPNHJHP-IZGCTLQUSA-N (4s,4as,5as,6r,12ar)-4-(dimethylamino)-1,6,10,11,12a-pentahydroxy-6-methyl-3,12-dioxo-4,4a,5,5a-tetrahydrotetracene-2-carboxamide;phosphoric acid Chemical compound OP(O)(O)=O.C1=CC=C2[C@@](O)(C)[C@H]3C[C@H]4[C@H](N(C)C)C(=O)C(C(N)=O)=C(O)[C@@]4(O)C(=O)C3=C(O)C2=C1O PHXCSXYIPNHJHP-IZGCTLQUSA-N 0.000 description 1
- MIDXCONKKJTLDX-UHFFFAOYSA-N 3,5-dimethylcyclopentane-1,2-dione Chemical compound CC1CC(C)C(=O)C1=O MIDXCONKKJTLDX-UHFFFAOYSA-N 0.000 description 1
- QFDSMZGWVHEDHT-UHFFFAOYSA-N 3-ethoxy-4-hydroxybenzoic acid Chemical compound CCOC1=CC(C(O)=O)=CC=C1O QFDSMZGWVHEDHT-UHFFFAOYSA-N 0.000 description 1
- CSGBRIWXMBIKEM-UHFFFAOYSA-N 3-ethoxy-n,n-diethyl-4-hydroxybenzamide Chemical compound CCOC1=CC(C(=O)N(CC)CC)=CC=C1O CSGBRIWXMBIKEM-UHFFFAOYSA-N 0.000 description 1
- BSYNRYMUTXBXSQ-FOQJRBATSA-N 59096-14-9 Chemical compound CC(=O)OC1=CC=CC=C1[14C](O)=O BSYNRYMUTXBXSQ-FOQJRBATSA-N 0.000 description 1
- 235000007173 Abies balsamea Nutrition 0.000 description 1
- 208000030090 Acute Disease Diseases 0.000 description 1
- RMMXTBMQSGEXHJ-UHFFFAOYSA-N Aminophenazone Chemical compound O=C1C(N(C)C)=C(C)N(C)N1C1=CC=CC=C1 RMMXTBMQSGEXHJ-UHFFFAOYSA-N 0.000 description 1
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Natural products OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 1
- 239000004857 Balsam Substances 0.000 description 1
- 206010006448 Bronchiolitis Diseases 0.000 description 1
- 229910014033 C-OH Inorganic materials 0.000 description 1
- 208000017667 Chronic Disease Diseases 0.000 description 1
- 229910014570 C—OH Inorganic materials 0.000 description 1
- NOOLISFMXDJSKH-UHFFFAOYSA-N DL-menthol Natural products CC(C)C1CCC(C)CC1O NOOLISFMXDJSKH-UHFFFAOYSA-N 0.000 description 1
- 244000166124 Eucalyptus globulus Species 0.000 description 1
- 239000001293 FEMA 3089 Substances 0.000 description 1
- 244000018716 Impatiens biflora Species 0.000 description 1
- WXFIGDLSSYIKKV-RCOVLWMOSA-N L-Metaraminol Chemical compound C[C@H](N)[C@H](O)C1=CC=CC(O)=C1 WXFIGDLSSYIKKV-RCOVLWMOSA-N 0.000 description 1
- LIMFPAAAIVQRRD-BCGVJQADSA-N N-[2-[(3S,4R)-3-fluoro-4-methoxypiperidin-1-yl]pyrimidin-4-yl]-8-[(2R,3S)-2-methyl-3-(methylsulfonylmethyl)azetidin-1-yl]-5-propan-2-ylisoquinolin-3-amine Chemical compound F[C@H]1CN(CC[C@H]1OC)C1=NC=CC(=N1)NC=1N=CC2=C(C=CC(=C2C=1)C(C)C)N1[C@@H]([C@H](C1)CS(=O)(=O)C)C LIMFPAAAIVQRRD-BCGVJQADSA-N 0.000 description 1
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- JGSARLDLIJGVTE-MBNYWOFBSA-N Penicillin G Chemical compound N([C@H]1[C@H]2SC([C@@H](N2C1=O)C(O)=O)(C)C)C(=O)CC1=CC=CC=C1 JGSARLDLIJGVTE-MBNYWOFBSA-N 0.000 description 1
- WTARULDDTDQWMU-UHFFFAOYSA-N Pseudopinene Natural products C1C2C(C)(C)C1CCC2=C WTARULDDTDQWMU-UHFFFAOYSA-N 0.000 description 1
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- 241000779819 Syncarpia glomulifera Species 0.000 description 1
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- XCPQUQHBVVXMRQ-UHFFFAOYSA-N alpha-Fenchene Natural products C1CC2C(=C)CC1C2(C)C XCPQUQHBVVXMRQ-UHFFFAOYSA-N 0.000 description 1
- 229960000212 aminophenazone Drugs 0.000 description 1
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- 235000010323 ascorbic acid Nutrition 0.000 description 1
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- 239000003205 fragrance Substances 0.000 description 1
- LCWMKIHBLJLORW-UHFFFAOYSA-N gamma-carene Natural products C1CC(=C)CC2C(C)(C)C21 LCWMKIHBLJLORW-UHFFFAOYSA-N 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 125000005456 glyceride group Chemical group 0.000 description 1
- 238000005469 granulation Methods 0.000 description 1
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- 238000001990 intravenous administration Methods 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
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- 229940039009 isoproterenol Drugs 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- TYQCGQRIZGCHNB-JLAZNSOCSA-N l-ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(O)=C(O)C1=O TYQCGQRIZGCHNB-JLAZNSOCSA-N 0.000 description 1
- 201000009837 laryngotracheitis Diseases 0.000 description 1
- 229960004393 lidocaine hydrochloride Drugs 0.000 description 1
- 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 description 1
- 229910001629 magnesium chloride Inorganic materials 0.000 description 1
- 229940041616 menthol Drugs 0.000 description 1
- 229960003663 metaraminol Drugs 0.000 description 1
- 229960005181 morphine Drugs 0.000 description 1
- 201000009240 nasopharyngitis Diseases 0.000 description 1
- NCYVXEGFNDZQCU-UHFFFAOYSA-N nikethamide Chemical compound CCN(CC)C(=O)C1=CC=CN=C1 NCYVXEGFNDZQCU-UHFFFAOYSA-N 0.000 description 1
- 229960003226 nikethamide Drugs 0.000 description 1
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- 238000007911 parenteral administration Methods 0.000 description 1
- 229940049954 penicillin Drugs 0.000 description 1
- 239000010665 pine oil Substances 0.000 description 1
- 239000001739 pinus spp. Substances 0.000 description 1
- 230000002980 postoperative effect Effects 0.000 description 1
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- 230000035935 pregnancy Effects 0.000 description 1
- 208000008128 pulmonary tuberculosis Diseases 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 230000036387 respiratory rate Effects 0.000 description 1
- 235000003441 saturated fatty acids Nutrition 0.000 description 1
- 150000004671 saturated fatty acids Chemical class 0.000 description 1
- 229940001584 sodium metabisulfite Drugs 0.000 description 1
- 239000004296 sodium metabisulphite Substances 0.000 description 1
- QORXBAUTUJKXSW-UHFFFAOYSA-M sodium;2,7-ditert-butylnaphthalene-1-sulfonate Chemical compound [Na+].C1=CC(C(C)(C)C)=C(S([O-])(=O)=O)C2=CC(C(C)(C)C)=CC=C21 QORXBAUTUJKXSW-UHFFFAOYSA-M 0.000 description 1
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- 230000003068 static effect Effects 0.000 description 1
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- 229960005322 streptomycin Drugs 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 229960002180 tetracycline Drugs 0.000 description 1
- OFVLGDICTFRJMM-WESIUVDSSA-N tetracycline Chemical compound C1=CC=C2[C@](O)(C)[C@H]3C[C@H]4[C@H](N(C)C)C(O)=C(C(N)=O)C(=O)[C@@]4(O)C(O)=C3C(=O)C2=C1O OFVLGDICTFRJMM-WESIUVDSSA-N 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
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- 231100000041 toxicology testing Toxicity 0.000 description 1
- 201000008827 tuberculosis Diseases 0.000 description 1
- 229940036248 turpentine Drugs 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
Classifications
-
- 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
- C07D303/04—Compounds containing oxirane rings containing only hydrogen and carbon atoms in addition to the ring oxygen atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Epoxy Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IT2349070 | 1970-04-17 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE2166355A1 DE2166355A1 (de) | 1973-10-18 |
| DE2166355C2 true DE2166355C2 (de) | 1983-12-08 |
Family
ID=11207557
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2166355A Expired DE2166355C2 (de) | 1970-04-17 | 1971-03-24 | Verwendung von d,1-Sobrerol bei der Balsamtherapie der Atemwege |
| DE2114138A Expired DE2114138C3 (de) | 1970-04-17 | 1971-03-24 | Verfahren zur Herstellung von Sobrerol |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2114138A Expired DE2114138C3 (de) | 1970-04-17 | 1971-03-24 | Verfahren zur Herstellung von Sobrerol |
Country Status (12)
Families Citing this family (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IT1167772B (it) * | 1981-05-28 | 1987-05-13 | Poli Ind Chimica Spa | Associazione di farmaci ad azione fluidificante nelle secrezioni mucose e mucopurulente |
| IT1173551B (it) * | 1984-04-02 | 1987-06-24 | Corvi Camillo Spa | Derivato del p-aminofenolo con attivita' mucosecretolitica-fluidificante e antipiretica,procedimento per la sua preparazione e sue composizioni farmaceutiche |
| IT1196214B (it) * | 1984-08-08 | 1988-11-16 | Corvi Camillo Spa | Derivato del(-)-6,6-dimetilbiciclo(3.3.1)ept-2-ene-2-metanolo ad attivita' mucosecretolitica,procedimento per la sua preparazione e sue composizioni farmaceutiche |
| IT1180220B (it) * | 1984-08-08 | 1987-09-23 | Corvi Camillo Spa | Miscela di composti diastereoisomeri, ottenuti da (-)-5-(1-idrossi-1-metiletil)-2-metil-2-cicloesen-1-one, avente attivita' mucosecretolitica, procedimento per la sua preparazione e composizioni farmaceutiche che la contengono |
| IT1196215B (it) * | 1984-08-08 | 1988-11-16 | Corvi Camillo Spa | Derivato del (-)-6,6-dimetilbiciclo (3.1.1)ept-2-ene-2-etanolo,ad attivita' mucosecretolitica,procedimento per la sua preparazione e composizioni farmaceutiche che lo contengono |
| CH681060A5 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) * | 1990-08-22 | 1993-01-15 | Riace Ets | |
| KR20030047503A (ko) * | 2001-12-11 | 2003-06-18 | 진양제약주식회사 | 소브레롤·아세트아미노펜 복합 건조시럽제 및 액제 |
| WO2017043935A1 (ko) * | 2015-09-09 | 2017-03-16 | 한국생명공학연구원 | 소브레롤을 포함하는 근력 약화 관련 질환의 예방 또는 치료용 조성물 |
| WO2019002889A1 (en) * | 2017-06-30 | 2019-01-03 | Industrial Technology Research Institute | METHOD FOR TREATING AUTOIMMUNE NEUROLOGICAL DISEASE AND / OR NEURODEGENERATIVE DISEASE AND PHARMACEUTICAL FORMULAS FOR LIQUID GALENIC FORM AND CONTROLLED RELEASE GALENIC FORM |
| KR102804780B1 (ko) * | 2024-01-17 | 2025-05-15 | 주식회사 뉴롤메드 | 인지기능 장애의 치료용 조성물 |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2815378A (en) * | 1953-06-12 | 1957-12-03 | Glidden Co | Hydration of alpha-pinene oxide |
| US2949489A (en) * | 1958-06-23 | 1960-08-16 | Fmc Corp | Preparation of sobrerol |
| FR1248647A (fr) * | 1959-11-04 | 1960-12-23 | Fmc Corp | Procédé de préparation du sobrérol |
| NL6617286A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) * | 1966-12-09 | 1968-06-10 |
-
1970
- 1970-12-10 CH CH1833670A patent/CH568951A5/xx not_active IP Right Cessation
- 1970-12-18 YU YU3110/70A patent/YU35564B/xx unknown
-
1971
- 1971-01-04 CA CA101,886A patent/CA991657A/en not_active Expired
- 1971-02-04 FR FR7103723A patent/FR2086134B1/fr not_active Expired
- 1971-02-26 NL NLAANVRAGE7102639,A patent/NL179109C/xx not_active IP Right Cessation
- 1971-03-16 BE BE764323A patent/BE764323A/xx not_active IP Right Cessation
- 1971-03-24 DE DE2166355A patent/DE2166355C2/de not_active Expired
- 1971-03-24 DE DE2114138A patent/DE2114138C3/de not_active Expired
- 1971-04-14 AT AT313171A patent/AT317169B/de not_active IP Right Cessation
- 1971-04-17 ES ES390305A patent/ES390305A1/es not_active Expired
- 1971-04-19 GB GB1295580D patent/GB1295580A/en not_active Expired
-
1973
- 1973-08-14 IN IN1878/CAL/73A patent/IN138738B/en unknown
-
1982
- 1982-09-30 US US06/429,445 patent/US4639469A/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| DE2114138C3 (de) | 1981-06-19 |
| AT317169B (de) | 1974-08-12 |
| BE764323A (fr) | 1971-08-16 |
| DE2114138A1 (de) | 1971-11-04 |
| YU311070A (en) | 1980-09-25 |
| NL179109C (nl) | 1986-07-16 |
| CH568951A5 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1975-11-14 |
| IN138738B (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1976-03-27 |
| NL179109B (nl) | 1986-02-17 |
| NL7102639A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1971-10-19 |
| FR2086134A1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1971-12-31 |
| ES390305A1 (es) | 1974-06-16 |
| FR2086134B1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1974-09-27 |
| US4639469A (en) | 1987-01-27 |
| YU35564B (en) | 1981-04-30 |
| CA991657A (en) | 1976-06-22 |
| DE2166355A1 (de) | 1973-10-18 |
| DE2114138B2 (de) | 1973-10-25 |
| GB1295580A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1972-11-08 |
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