NO116803B - - Google Patents
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- Publication number
- NO116803B NO116803B NO166993A NO16699367A NO116803B NO 116803 B NO116803 B NO 116803B NO 166993 A NO166993 A NO 166993A NO 16699367 A NO16699367 A NO 16699367A NO 116803 B NO116803 B NO 116803B
- Authority
- NO
- Norway
- Prior art keywords
- acid
- pantothenol
- compounds
- formula
- acyl group
- Prior art date
Links
- 239000002253 acid Substances 0.000 claims description 26
- SNPLKNRPJHDVJA-ZETCQYMHSA-N D-panthenol Chemical compound OCC(C)(C)[C@@H](O)C(=O)NCCCO SNPLKNRPJHDVJA-ZETCQYMHSA-N 0.000 claims description 14
- 238000000034 method Methods 0.000 claims description 8
- QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Substances CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 5
- 125000002252 acyl group Chemical group 0.000 claims description 4
- 150000002148 esters Chemical class 0.000 claims description 4
- 238000002360 preparation method Methods 0.000 claims description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
- 125000002015 acyclic group Chemical group 0.000 claims description 2
- 125000004122 cyclic group Chemical group 0.000 claims description 2
- 230000032050 esterification Effects 0.000 claims description 2
- 238000005886 esterification reaction Methods 0.000 claims description 2
- 150000001875 compounds Chemical class 0.000 description 22
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 19
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 14
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 12
- 239000000203 mixture Substances 0.000 description 8
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 7
- 239000002904 solvent Substances 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
- 239000003208 petroleum Substances 0.000 description 6
- -1 terpenyl acetic acid Chemical compound 0.000 description 6
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- 239000011230 binding agent Substances 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 238000010828 elution Methods 0.000 description 4
- 150000004820 halides Chemical class 0.000 description 4
- 230000035876 healing Effects 0.000 description 4
- 150000007530 organic bases Chemical group 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- 208000027418 Wounds and injury Diseases 0.000 description 3
- 235000011054 acetic acid Nutrition 0.000 description 3
- 150000008064 anhydrides Chemical class 0.000 description 3
- 238000004587 chromatography analysis Methods 0.000 description 3
- 150000005690 diesters Chemical class 0.000 description 3
- 238000001704 evaporation Methods 0.000 description 3
- 230000008020 evaporation Effects 0.000 description 3
- 229940007703 farnesyl acetate Drugs 0.000 description 3
- 230000000622 irritating effect Effects 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 239000003921 oil Substances 0.000 description 3
- 235000019198 oils Nutrition 0.000 description 3
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- 239000002562 thickening agent Substances 0.000 description 3
- 230000000699 topical effect Effects 0.000 description 3
- GHOKWGTUZJEAQD-ZETCQYMHSA-N (D)-(+)-Pantothenic acid Chemical compound OCC(C)(C)[C@@H](O)C(=O)NCCC(O)=O GHOKWGTUZJEAQD-ZETCQYMHSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- WFDIJRYMOXRFFG-UHFFFAOYSA-N acetic acid anhydride Natural products CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 239000004480 active ingredient Substances 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- GJWSUKYXUMVMGX-UHFFFAOYSA-N citronellic acid Chemical compound OC(=O)CC(C)CCC=C(C)C GJWSUKYXUMVMGX-UHFFFAOYSA-N 0.000 description 2
- 239000006071 cream Substances 0.000 description 2
- 230000006378 damage Effects 0.000 description 2
- 239000012442 inert solvent Substances 0.000 description 2
- 208000014674 injury Diseases 0.000 description 2
- 235000019388 lanolin Nutrition 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 239000002674 ointment Substances 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- 150000005691 triesters Chemical class 0.000 description 2
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 2
- FQTLCLSUCSAZDY-UHFFFAOYSA-N (+) E(S) nerolidol Natural products CC(C)=CCCC(C)=CCCC(C)(O)C=C FQTLCLSUCSAZDY-UHFFFAOYSA-N 0.000 description 1
- ZHYZQXUYZJNEHD-CLFYSBASSA-N (2z)-3,7-dimethylocta-2,6-dienoic acid Chemical compound CC(C)=CCC\C(C)=C/C(O)=O ZHYZQXUYZJNEHD-CLFYSBASSA-N 0.000 description 1
- UAXLWQGEEXDYOB-JXMROGBWSA-N (3e)-4,8-dimethylnona-3,7-dienoic acid Chemical compound CC(C)=CCC\C(C)=C\CC(O)=O UAXLWQGEEXDYOB-JXMROGBWSA-N 0.000 description 1
- HPOYZGTYWKRTPU-DHZHZOJOSA-N (4e)-5,9-dimethyldeca-4,8-dienoic acid Chemical compound CC(C)=CCC\C(C)=C\CCC(O)=O HPOYZGTYWKRTPU-DHZHZOJOSA-N 0.000 description 1
- VOKDWPMRYSKGTB-NCZFFCEISA-N (4e,8e)-5,9,13-trimethyltetradeca-4,8,12-trienoic acid Chemical compound CC(C)=CCC\C(C)=C\CC\C(C)=C\CCC(O)=O VOKDWPMRYSKGTB-NCZFFCEISA-N 0.000 description 1
- WOAFHTKZUQDUJD-UHFFFAOYSA-N 5,9,13-trimethyltetradeca-4,8,12-trienoyl chloride Chemical compound CC(C)=CCCC(C)=CCCC(C)=CCCC(Cl)=O WOAFHTKZUQDUJD-UHFFFAOYSA-N 0.000 description 1
- 241000700198 Cavia Species 0.000 description 1
- GHOKWGTUZJEAQD-UHFFFAOYSA-N Chick antidermatitis factor Natural products OCC(C)(C)C(O)C(=O)NCCC(O)=O GHOKWGTUZJEAQD-UHFFFAOYSA-N 0.000 description 1
- 229930008398 Citronellate Natural products 0.000 description 1
- 206010061245 Internal injury Diseases 0.000 description 1
- 239000004166 Lanolin Substances 0.000 description 1
- 241000699670 Mus sp. Species 0.000 description 1
- FQTLCLSUCSAZDY-ATGUSINASA-N Nerolidol Chemical compound CC(C)=CCC\C(C)=C\CC[C@](C)(O)C=C FQTLCLSUCSAZDY-ATGUSINASA-N 0.000 description 1
- 241000283973 Oryctolagus cuniculus Species 0.000 description 1
- 235000019483 Peanut oil Nutrition 0.000 description 1
- 241000700159 Rattus Species 0.000 description 1
- 208000028990 Skin injury Diseases 0.000 description 1
- 206010072170 Skin wound Diseases 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- 208000007107 Stomach Ulcer Diseases 0.000 description 1
- 206010052428 Wound Diseases 0.000 description 1
- CEGOLXSVJUTHNZ-UHFFFAOYSA-K aluminium tristearate Chemical compound [Al+3].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O CEGOLXSVJUTHNZ-UHFFFAOYSA-K 0.000 description 1
- 229940063655 aluminum stearate Drugs 0.000 description 1
- 239000003242 anti bacterial agent Substances 0.000 description 1
- 235000013871 bee wax Nutrition 0.000 description 1
- 239000012166 beeswax Substances 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 235000019438 castor oil Nutrition 0.000 description 1
- 239000004359 castor oil Substances 0.000 description 1
- 229940082500 cetostearyl alcohol Drugs 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 239000012230 colorless oil Substances 0.000 description 1
- 239000000356 contaminant Substances 0.000 description 1
- 210000004087 cornea Anatomy 0.000 description 1
- GGSUCNLOZRCGPQ-UHFFFAOYSA-N diethylaniline Chemical compound CCN(CC)C1=CC=CC=C1 GGSUCNLOZRCGPQ-UHFFFAOYSA-N 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 239000003937 drug carrier Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000003480 eluent Substances 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 239000003889 eye drop Substances 0.000 description 1
- 229940012356 eye drops Drugs 0.000 description 1
- 210000001035 gastrointestinal tract Anatomy 0.000 description 1
- 239000003349 gelling agent Substances 0.000 description 1
- 239000003862 glucocorticoid Substances 0.000 description 1
- ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Natural products CCCCCC[C@@H](O)CC=CCCCCCCCC(=O)OC[C@@H](COC(=O)CCCCCCCC=CC[C@@H](O)CCCCCC)OC(=O)CCCCCCCC=CC[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-XOQCFJPHSA-N 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 230000007794 irritation Effects 0.000 description 1
- 229940039717 lanolin Drugs 0.000 description 1
- 229940057995 liquid paraffin Drugs 0.000 description 1
- 231100000053 low toxicity Toxicity 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 230000002503 metabolic effect Effects 0.000 description 1
- 210000004877 mucosa Anatomy 0.000 description 1
- 229940100662 nasal drops Drugs 0.000 description 1
- WASNIKZYIWZQIP-AWEZNQCLSA-N nerolidol Natural products CC(=CCCC(=CCC[C@@H](O)C=C)C)C WASNIKZYIWZQIP-AWEZNQCLSA-N 0.000 description 1
- 230000037311 normal skin Effects 0.000 description 1
- GLDOVTGHNKAZLK-UHFFFAOYSA-N octadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCO GLDOVTGHNKAZLK-UHFFFAOYSA-N 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 235000019161 pantothenic acid Nutrition 0.000 description 1
- 239000011713 pantothenic acid Substances 0.000 description 1
- 229940055726 pantothenic acid Drugs 0.000 description 1
- 235000020957 pantothenol Nutrition 0.000 description 1
- 239000011619 pantothenol Substances 0.000 description 1
- 229940056211 paraffin Drugs 0.000 description 1
- 239000012188 paraffin wax Substances 0.000 description 1
- 239000000312 peanut oil Substances 0.000 description 1
- 210000003899 penis Anatomy 0.000 description 1
- 239000000825 pharmaceutical preparation Substances 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 239000006187 pill Substances 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 229940068917 polyethylene glycols Drugs 0.000 description 1
- 230000001737 promoting effect Effects 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 239000000375 suspending agent Substances 0.000 description 1
- 229940037128 systemic glucocorticoids Drugs 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 150000003505 terpenes Chemical class 0.000 description 1
- 235000007586 terpenes Nutrition 0.000 description 1
- OULAJFUGPPVRBK-UHFFFAOYSA-N tetratriacontyl alcohol Natural products CCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCO OULAJFUGPPVRBK-UHFFFAOYSA-N 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 239000005526 vasoconstrictor agent Substances 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 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
- A61K31/21—Esters, e.g. nitroglycerine, selenocyanates
- A61K31/215—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB8243/66A GB1170132A (en) | 1966-02-24 | 1966-02-24 | Esters of d-Pantothenol |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NO116803B true NO116803B (de) | 1969-05-27 |
Family
ID=9848743
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO166993A NO116803B (de) | 1966-02-24 | 1967-02-23 |
Country Status (11)
| Country | Link |
|---|---|
| US (1) | US3584018A (de) |
| AT (1) | AT282836B (de) |
| BE (1) | BE694366A (de) |
| CH (1) | CH480298A (de) |
| DE (1) | DE1618536B1 (de) |
| ES (1) | ES337211A1 (de) |
| FR (2) | FR6351M (de) |
| GB (1) | GB1170132A (de) |
| GR (1) | GR33482B (de) |
| NL (2) | NL6702965A (de) |
| NO (1) | NO116803B (de) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4634729A (en) * | 1985-09-23 | 1987-01-06 | Union Camp Corporation | Terpene-based ester tackifiers |
| IT1201481B (it) * | 1985-10-08 | 1989-02-02 | Prodotti Antibiotici Spa | Pantotenil derivati |
| RU2045515C1 (ru) * | 1993-06-30 | 1995-10-10 | Научно-производственное объединение "Витамины" | Кетопантоиламинобутират кальция, обладающий седативным действием |
| RU2054415C1 (ru) * | 1994-03-02 | 1996-02-20 | Товарищество с ограниченной ответственностью "Пант" | Кетопантотенат кальция, обладающий ацетилирующей активностью d-пантотената кальция |
| RU2054000C1 (ru) * | 1994-03-02 | 1996-02-10 | Товарищество с ограниченной ответственностью "Пант" | Кетопантенол, обладающий ацетилирующей активностью d-пантотената кальция |
| FR2902659A1 (fr) | 2006-06-23 | 2007-12-28 | Pierre Fabre Medicament Sa | Ester de dha et son utilisation dans le traitement et la prevention des maladies cardiovasculaires |
| FR2963790B1 (fr) * | 2010-08-11 | 2012-09-28 | Pf Medicament | Docosahexaeneoate de panthenyle et son utilisation dans le traitement et la prevention des maladies cardiovasculaires |
-
0
- NL NL133049D patent/NL133049C/xx active
-
1966
- 1966-02-24 GB GB8243/66A patent/GB1170132A/en not_active Expired
-
1967
- 1967-02-11 GR GR670133482A patent/GR33482B/el unknown
- 1967-02-13 US US615372A patent/US3584018A/en not_active Expired - Lifetime
- 1967-02-20 AT AT166367A patent/AT282836B/de not_active IP Right Cessation
- 1967-02-21 BE BE694366D patent/BE694366A/xx unknown
- 1967-02-22 FR FR95951A patent/FR6351M/fr not_active Expired
- 1967-02-22 FR FR95958A patent/FR1512123A/fr not_active Expired
- 1967-02-23 NO NO166993A patent/NO116803B/no unknown
- 1967-02-23 CH CH267867A patent/CH480298A/de not_active IP Right Cessation
- 1967-02-23 ES ES337211A patent/ES337211A1/es not_active Expired
- 1967-02-24 DE DE1967J0033070 patent/DE1618536B1/de active Pending
- 1967-02-24 NL NL6702965A patent/NL6702965A/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| AT282836B (de) | 1970-07-10 |
| ES337211A1 (es) | 1968-06-01 |
| CH480298A (de) | 1969-10-31 |
| NL133049C (de) | |
| FR6351M (de) | 1968-10-07 |
| DE1618536B1 (de) | 1972-02-03 |
| GB1170132A (en) | 1969-11-12 |
| BE694366A (de) | 1967-08-21 |
| US3584018A (en) | 1971-06-08 |
| FR1512123A (fr) | 1968-02-02 |
| GR33482B (el) | 1967-12-08 |
| NL6702965A (de) | 1967-08-25 |
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