NZ208900A - N-phenylmethylalkanamide (and thioamide) derivatives and pharmaceutical compositions - Google Patents
N-phenylmethylalkanamide (and thioamide) derivatives and pharmaceutical compositionsInfo
- Publication number
- NZ208900A NZ208900A NZ208900A NZ20890084A NZ208900A NZ 208900 A NZ208900 A NZ 208900A NZ 208900 A NZ208900 A NZ 208900A NZ 20890084 A NZ20890084 A NZ 20890084A NZ 208900 A NZ208900 A NZ 208900A
- Authority
- NZ
- New Zealand
- Prior art keywords
- methylenealkanamide
- composition
- methylene
- pharmaceutically
- compound
- Prior art date
Links
- 239000008194 pharmaceutical composition Substances 0.000 title 1
- 150000003556 thioamides Chemical class 0.000 title 1
- 239000000203 mixture Substances 0.000 claims description 73
- 230000036592 analgesia Effects 0.000 claims description 29
- 150000001875 compounds Chemical class 0.000 claims description 20
- 238000000034 method Methods 0.000 claims description 16
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 claims description 15
- 241000282414 Homo sapiens Species 0.000 claims description 11
- 150000003839 salts Chemical class 0.000 claims description 11
- 241001465754 Metazoa Species 0.000 claims description 9
- 125000004432 carbon atom Chemical group C* 0.000 claims description 9
- 239000003937 drug carrier Substances 0.000 claims description 8
- 150000002148 esters Chemical class 0.000 claims description 8
- 238000007911 parenteral administration Methods 0.000 claims description 8
- 241000282412 Homo Species 0.000 claims description 7
- 238000011200 topical administration Methods 0.000 claims description 4
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims description 3
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 3
- 239000011734 sodium Substances 0.000 claims description 3
- 229910052708 sodium Inorganic materials 0.000 claims description 3
- -1 (4-acetoxy-3-methoxy-phenyl)methyl Chemical group 0.000 claims description 2
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 claims description 2
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 claims description 2
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims description 2
- 239000011575 calcium Substances 0.000 claims description 2
- 229910052791 calcium Inorganic materials 0.000 claims description 2
- 239000011777 magnesium Substances 0.000 claims description 2
- 229910052749 magnesium Inorganic materials 0.000 claims description 2
- 239000011591 potassium Substances 0.000 claims description 2
- 229910052700 potassium Inorganic materials 0.000 claims description 2
- BXWNKGSJHAJOGX-UHFFFAOYSA-N hexadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCO BXWNKGSJHAJOGX-UHFFFAOYSA-N 0.000 claims 2
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- ALSTYHKOOCGGFT-KTKRTIGZSA-N (9Z)-octadecen-1-ol Chemical compound CCCCCCCC\C=C/CCCCCCCCO ALSTYHKOOCGGFT-KTKRTIGZSA-N 0.000 claims 1
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- YKPUWZUDDOIDPM-SOFGYWHQSA-N capsaicin Chemical compound COC1=CC(CNC(=O)CCCC\C=C\C(C)C)=CC=C1O YKPUWZUDDOIDPM-SOFGYWHQSA-N 0.000 description 22
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- 239000000047 product Substances 0.000 description 16
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- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 12
- 230000000202 analgesic effect Effects 0.000 description 10
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- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 8
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- VVWPSAPZUZXYCM-UHFFFAOYSA-N 9-methoxy-9-oxononanoic acid Chemical compound COC(=O)CCCCCCCC(O)=O VVWPSAPZUZXYCM-UHFFFAOYSA-N 0.000 description 6
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- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- 239000006186 oral dosage form Substances 0.000 description 6
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- VMKOFRJSULQZRM-UHFFFAOYSA-N 1-bromooctane Chemical compound CCCCCCCCBr VMKOFRJSULQZRM-UHFFFAOYSA-N 0.000 description 3
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- OPZKBPQVWDSATI-KHPPLWFESA-N N-Vanillyloleamide Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)NCC1=CC=C(O)C(OC)=C1 OPZKBPQVWDSATI-KHPPLWFESA-N 0.000 description 2
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- 229940075614 colloidal silicon dioxide Drugs 0.000 description 1
- 238000004040 coloring Methods 0.000 description 1
- 239000007891 compressed tablet Substances 0.000 description 1
- 239000013256 coordination polymer Substances 0.000 description 1
- 235000012343 cottonseed oil Nutrition 0.000 description 1
- 239000002385 cottonseed oil Substances 0.000 description 1
- 239000006071 cream Substances 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 230000009429 distress Effects 0.000 description 1
- 239000003974 emollient agent Substances 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- DQYBDCGIPTYXML-UHFFFAOYSA-N ethoxyethane;hydrate Chemical compound O.CCOCC DQYBDCGIPTYXML-UHFFFAOYSA-N 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 238000011049 filling Methods 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 239000000499 gel Substances 0.000 description 1
- 235000011187 glycerol Nutrition 0.000 description 1
- 229960005150 glycerol Drugs 0.000 description 1
- 229940081141 hexadecanamide Drugs 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000003752 hydrotrope Substances 0.000 description 1
- 238000007654 immersion Methods 0.000 description 1
- 229960000905 indomethacin Drugs 0.000 description 1
- 230000001939 inductive effect Effects 0.000 description 1
- 208000014674 injury Diseases 0.000 description 1
- 238000007918 intramuscular administration Methods 0.000 description 1
- 238000007912 intraperitoneal administration Methods 0.000 description 1
- 238000007913 intrathecal administration Methods 0.000 description 1
- 238000001990 intravenous administration Methods 0.000 description 1
- 230000007794 irritation Effects 0.000 description 1
- 210000001503 joint Anatomy 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 231100001231 less toxic Toxicity 0.000 description 1
- 229960003406 levorphanol Drugs 0.000 description 1
- 239000006210 lotion Substances 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- MAGPZHKLEZXLNU-UHFFFAOYSA-N mandelamide Chemical class NC(=O)C(O)C1=CC=CC=C1 MAGPZHKLEZXLNU-UHFFFAOYSA-N 0.000 description 1
- 239000000594 mannitol Substances 0.000 description 1
- 235000010355 mannitol Nutrition 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- QLNWXBAGRTUKKI-UHFFFAOYSA-N metacetamol Chemical compound CC(=O)NC1=CC=CC(O)=C1 QLNWXBAGRTUKKI-UHFFFAOYSA-N 0.000 description 1
- 229960001797 methadone Drugs 0.000 description 1
- HZVOZRGWRWCICA-UHFFFAOYSA-N methanediyl Chemical group [CH2] HZVOZRGWRWCICA-UHFFFAOYSA-N 0.000 description 1
- 239000004292 methyl p-hydroxybenzoate Substances 0.000 description 1
- 235000010270 methyl p-hydroxybenzoate Nutrition 0.000 description 1
- LSEFCHWGJNHZNT-UHFFFAOYSA-M methyl(triphenyl)phosphanium;bromide Chemical compound [Br-].C=1C=CC=CC=1[P+](C=1C=CC=CC=1)(C)C1=CC=CC=C1 LSEFCHWGJNHZNT-UHFFFAOYSA-M 0.000 description 1
- 229960002216 methylparaben Drugs 0.000 description 1
- 229940016286 microcrystalline cellulose Drugs 0.000 description 1
- 235000019813 microcrystalline cellulose Nutrition 0.000 description 1
- 239000008108 microcrystalline cellulose Substances 0.000 description 1
- JDRMYOQETPMYQX-UHFFFAOYSA-N monomethyl succinate Chemical compound COC(=O)CCC(O)=O JDRMYOQETPMYQX-UHFFFAOYSA-N 0.000 description 1
- 230000036651 mood Effects 0.000 description 1
- 229960000938 nalorphine Drugs 0.000 description 1
- 229960004127 naloxone Drugs 0.000 description 1
- UZHSEJADLWPNLE-GRGSLBFTSA-N naloxone Chemical compound O=C([C@@H]1O2)CC[C@@]3(O)[C@H]4CC5=CC=C(O)C2=C5[C@@]13CCN4CC=C UZHSEJADLWPNLE-GRGSLBFTSA-N 0.000 description 1
- 239000004081 narcotic agent Substances 0.000 description 1
- 239000003887 narcotic antagonist Substances 0.000 description 1
- 210000001640 nerve ending Anatomy 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 235000019198 oils Nutrition 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 230000008058 pain sensation Effects 0.000 description 1
- 229960005489 paracetamol Drugs 0.000 description 1
- 210000001428 peripheral nervous system Anatomy 0.000 description 1
- 229960000482 pethidine Drugs 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 229960003893 phenacetin Drugs 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 229960002895 phenylbutazone Drugs 0.000 description 1
- VYMDGNCVAMGZFE-UHFFFAOYSA-N phenylbutazonum Chemical compound O=C1C(CCCC)C(=O)N(C=2C=CC=CC=2)N1C1=CC=CC=C1 VYMDGNCVAMGZFE-UHFFFAOYSA-N 0.000 description 1
- 239000008363 phosphate buffer Substances 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 229920005862 polyol Polymers 0.000 description 1
- 150000003077 polyols Chemical class 0.000 description 1
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
- 229940069328 povidone Drugs 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000004405 propyl p-hydroxybenzoate Substances 0.000 description 1
- 235000010232 propyl p-hydroxybenzoate Nutrition 0.000 description 1
- 235000013772 propylene glycol Nutrition 0.000 description 1
- 229960003415 propylparaben Drugs 0.000 description 1
- 230000003236 psychic effect Effects 0.000 description 1
- 235000019633 pungent taste Nutrition 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- CVHZOJJKTDOEJC-UHFFFAOYSA-N saccharin Chemical compound C1=CC=C2C(=O)NS(=O)(=O)C2=C1 CVHZOJJKTDOEJC-UHFFFAOYSA-N 0.000 description 1
- 235000019204 saccharin Nutrition 0.000 description 1
- 229940081974 saccharin Drugs 0.000 description 1
- 239000000901 saccharin and its Na,K and Ca salt Substances 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- 238000010898 silica gel chromatography Methods 0.000 description 1
- WXMKPNITSTVMEF-UHFFFAOYSA-M sodium benzoate Chemical compound [Na+].[O-]C(=O)C1=CC=CC=C1 WXMKPNITSTVMEF-UHFFFAOYSA-M 0.000 description 1
- 239000004299 sodium benzoate Substances 0.000 description 1
- 235000010234 sodium benzoate Nutrition 0.000 description 1
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 230000000638 stimulation Effects 0.000 description 1
- 238000007920 subcutaneous administration Methods 0.000 description 1
- 239000007929 subcutaneous injection Substances 0.000 description 1
- 238000010254 subcutaneous injection Methods 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 150000008163 sugars Chemical class 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 239000000375 suspending agent Substances 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 238000007910 systemic administration Methods 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 235000012222 talc Nutrition 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- 230000008733 trauma Effects 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 239000003981 vehicle Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/09—Preparation of carboxylic acids or their salts, halides or anhydrides from carboxylic acid esters or lactones
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/02—Drugs for disorders of the nervous system for peripheral neuropathies
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/04—Centrally acting analgesics, e.g. opioids
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/58—Preparation of carboxylic acid halides
- C07C51/60—Preparation of carboxylic acid halides by conversion of carboxylic acids or their anhydrides or esters, lactones, salts into halides with the same carboxylic acid part
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Medicinal Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Neurology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Biomedical Technology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmacology & Pharmacy (AREA)
- Neurosurgery (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pain & Pain Management (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US06/514,205 US4544668A (en) | 1983-07-14 | 1983-07-14 | Compounds and compositions useful for producing analgesia |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NZ208900A true NZ208900A (en) | 1988-03-30 |
Family
ID=24046223
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NZ208900A NZ208900A (en) | 1983-07-14 | 1984-07-13 | N-phenylmethylalkanamide (and thioamide) derivatives and pharmaceutical compositions |
Country Status (15)
Families Citing this family (26)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4493848A (en) * | 1983-07-14 | 1985-01-15 | The Procter & Gamble Company | Compositions and methods useful for producing analgesia |
| US4681897A (en) * | 1984-01-16 | 1987-07-21 | The Procter & Gamble Company | Pharmaceutical products providing enhanced analgesia |
| GB2178031B (en) | 1985-06-10 | 1989-07-26 | Procter & Gamble | Phenylacetic acid amides having anti-inflammatory and analgesic activity |
| US4990533A (en) * | 1985-12-20 | 1991-02-05 | Warner-Lambert Co. | Benzoic acid and benzoic acid ester derivatives having anti-inflammatory and analgesic activity |
| US4689182A (en) * | 1985-12-20 | 1987-08-25 | Warner-Lambert Company | Benzoic acid and benzoic acid ester derivatives having anti-inflammatory and analgesic activity |
| US4980366A (en) * | 1986-08-19 | 1990-12-25 | Warner-Lambert Co. | Amide, sulfonamide, urea, carbamate, thiocarbamate, and thiourea derivatives of 4'hydroxybenzylamine having anti-inflammatory and analgesic activity |
| US5045565A (en) * | 1987-03-09 | 1991-09-03 | The Procter & Gamble Company | Novel compounds, pharmaceutical compositions, and methods for treating inflammation and pain |
| US5099030A (en) * | 1987-03-09 | 1992-03-24 | The Procter & Gamble Company | Novel compounds, pharmaceutical compositions, and methods for treating inflammation and pain |
| US5461075A (en) * | 1988-06-17 | 1995-10-24 | The Procter & Gamble Company | Use of vanilloids for the prevention of lesions due to herpes simplex infections |
| US5762963A (en) * | 1995-06-07 | 1998-06-09 | Emory University | Method and compositions for controlling oral and pharyngeal pain using capsaicinoids |
| US6248788B1 (en) | 1996-11-06 | 2001-06-19 | The Regents Of The University Of California | Therapeutic method with capsaicin and capasicin analogs |
| US6239180B1 (en) | 1995-11-08 | 2001-05-29 | The Regents Of The University Of California | Transdermal therapeutic device and method with capsaicin and capsaicin analogs |
| AU7389098A (en) | 1997-05-16 | 1998-12-08 | Brigham And Women's Hospital | Local anesthetic formulations |
| US6689399B1 (en) | 2000-03-16 | 2004-02-10 | James R. Dickson | Transdermal delivery of an anti-inflammatory composition |
| US7192612B2 (en) * | 2001-02-22 | 2007-03-20 | Purdue Research Foundation | Compositions and methods based on synergies between capsicum extracts and tea catechins for prevention and treatment of cancer |
| AU2002254007B2 (en) | 2001-02-22 | 2006-09-21 | Purdue Research Foundation | Compositions based on vanilloid-catechin synergies for prevention and treatment of cancer |
| CA2522028C (en) | 2003-04-10 | 2011-11-01 | Neurogesx, Inc. | Methods and compositions for administration of trpv1 agonists |
| US20080268092A1 (en) * | 2004-12-01 | 2008-10-30 | Dacanay Rhodel G | Capsaicin Nutritional Supplement |
| CA2597651A1 (en) * | 2005-02-14 | 2006-08-24 | Neurogesx, Inc. | Device for delivery of trpv1 agonists |
| CA2602832A1 (en) * | 2005-03-30 | 2006-10-05 | Keith R. Bley | Low-concentration capsaicin patch and methods for treating neuropathic pain |
| BRPI0610333A2 (pt) * | 2005-04-25 | 2010-06-15 | Neurogesx Inc | compostos agonistas de trpv1 e métodos de fazer e usar os mesmos |
| US8952152B2 (en) | 2009-03-24 | 2015-02-10 | Proteus S.A. | Methods for purifying phycotoxins, pharmaceutical compositions containing purified phycotoxins, and methods of use thereof |
| US20120027693A1 (en) | 2010-07-27 | 2012-02-02 | Bean Bruce P | Methods and compositions for preventing and relieving muscle cramps and for recovery from neuromuscular irritability and fatigue following exercise |
| JP2014504184A (ja) | 2010-12-01 | 2014-02-20 | スパイナル・モデュレーション・インコーポレイテッド | 神経構造への薬剤の直接送達 |
| KR20210062693A (ko) | 2013-03-15 | 2021-05-31 | 더 칠드런스 메디칼 센터 코포레이션 | 지속성 국소 마취용 네오삭시톡신 조합 제형 |
| EP3570861A4 (en) | 2017-01-23 | 2020-11-18 | Flex Pharma, Inc. | COMPOSITIONS AND METHODS TO IMPROVE EXERCISE EFFICIENCY |
Family Cites Families (19)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE938014C (de) * | 1952-11-05 | 1956-01-19 | Beiersdorf & Co A G P | Verfahren zur Herstellung kristallisierter Vanillylamide |
| DE1166766B (de) * | 1961-08-04 | 1964-04-02 | Boehringer Sohn Ingelheim | Verfahren zur Herstellung von neuen Phenylalkylcarbonsaeureamiden |
| FR1336388A (fr) * | 1961-08-04 | 1963-08-30 | Boehringer Sohn Ingelheim | Procédé pour la préparation des amides d'acides phénylalcoylcarboxyliques |
| BE626897A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) * | 1962-01-17 | |||
| US3621043A (en) * | 1963-02-06 | 1971-11-16 | Sumitomo Chemical Co | N-substituted octadecadienoic acid amides as cholesterol lowering agents |
| GB1051286A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) * | 1964-04-28 | |||
| SE353319B (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) * | 1964-08-15 | 1973-01-29 | Sumitomo Chemical Co | |
| US3558500A (en) * | 1968-02-07 | 1971-01-26 | Buckman Labor Inc | Method for the control of scale using n,n-dimethylamides of 18 carbon unsaturated carboxylic acids |
| US3920523A (en) * | 1971-03-17 | 1975-11-18 | Akzona Inc | Thin film evaporation of a crude amide feed in mixture with an alkali metal hydroxide |
| US3888893A (en) * | 1971-06-14 | 1975-06-10 | John B Siddall | Unsaturated amides |
| US3816484A (en) * | 1971-10-08 | 1974-06-11 | Zoecon Corp | Aliphatic hydrocarbon 2,4-dienamides |
| US3803185A (en) * | 1971-11-22 | 1974-04-09 | Zoecon Corp | Novel 2,4-dienamides |
| JPS5619344B2 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) * | 1972-11-11 | 1981-05-07 | ||
| DE2752366A1 (de) * | 1977-11-24 | 1979-05-31 | Bayer Ag | 3,3-dimethyl-4-penten-thiosaeureamide und verfahren zu ihrer herstellung |
| US4238508A (en) * | 1979-08-17 | 1980-12-09 | The Research Foundation Of State University Of New York | Method for analgesia using 3-hydroxyacetanilide |
| US4313958A (en) * | 1980-10-24 | 1982-02-02 | The Procter & Gamble Company | Method of producing analgesia |
| US4401663A (en) * | 1981-06-30 | 1983-08-30 | The Procter & Gamble Company | Novel sulfonamide derivatives |
| JPS6139413A (ja) * | 1984-07-31 | 1986-02-25 | 日立電線株式会社 | 弛度抑制型電線の製造方法 |
| JPS6147752A (ja) * | 1984-08-14 | 1986-03-08 | Fujikura Ltd | 難燃性組成物 |
-
1983
- 1983-07-14 US US06/514,205 patent/US4544668A/en not_active Expired - Lifetime
-
1984
- 1984-07-11 EP EP84304730A patent/EP0132115B1/en not_active Expired
- 1984-07-11 DE DE8484304730T patent/DE3460821D1/de not_active Expired
- 1984-07-11 GB GB08417626A patent/GB2144416B/en not_active Expired
- 1984-07-11 ZA ZA845349A patent/ZA845349B/xx unknown
- 1984-07-12 CA CA000458763A patent/CA1244048A/en not_active Expired
- 1984-07-13 NZ NZ208900A patent/NZ208900A/en unknown
- 1984-07-13 AU AU30588/84A patent/AU560396B2/en not_active Ceased
- 1984-07-13 JP JP59145861A patent/JPS60136545A/ja active Granted
- 1984-07-13 DK DK345984A patent/DK164852C/da not_active IP Right Cessation
- 1984-07-13 PH PH30979A patent/PH20373A/en unknown
- 1984-07-13 IE IE1815/84A patent/IE57568B1/en not_active IP Right Cessation
-
1987
- 1987-09-30 MY MYPI87002521A patent/MY101483A/en unknown
-
1990
- 1990-06-06 SG SG403/90A patent/SG40390G/en unknown
- 1990-08-02 HK HK585/90A patent/HK58590A/xx not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| GB2144416B (en) | 1987-06-17 |
| IE841815L (en) | 1985-01-14 |
| PH20373A (en) | 1986-12-08 |
| DE3460821D1 (en) | 1986-10-30 |
| EP0132115A1 (en) | 1985-01-23 |
| IE57568B1 (en) | 1992-12-16 |
| DK345984A (da) | 1985-01-15 |
| GB2144416A (en) | 1985-03-06 |
| HK58590A (en) | 1990-08-10 |
| EP0132115B1 (en) | 1986-09-24 |
| AU560396B2 (en) | 1987-04-02 |
| AU3058884A (en) | 1985-01-17 |
| ZA845349B (en) | 1985-03-27 |
| SG40390G (en) | 1990-08-03 |
| DK164852C (da) | 1993-01-18 |
| CA1244048A (en) | 1988-11-01 |
| JPH0472821B2 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1992-11-19 |
| MY101483A (en) | 1991-11-18 |
| GB8417626D0 (en) | 1984-08-15 |
| JPS60136545A (ja) | 1985-07-20 |
| US4544668A (en) | 1985-10-01 |
| DK345984D0 (da) | 1984-07-13 |
| DK164852B (da) | 1992-08-31 |
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