NO310456B1 - Diaromatiske dienylforbindelser, farmasöytiske og kosmetiske preparater inneholdende slike forbindelser, samt anvendelse - Google Patents

Diaromatiske dienylforbindelser, farmasöytiske og kosmetiske preparater inneholdende slike forbindelser, samt anvendelse Download PDF

Info

Publication number: NO310456B1
Authority: NO; Norway
Prior art keywords: tetrahydro; propynyl; naphthyl; tetramethyl; hydroxy
Prior art date: 1996-03-14

Application number

NO19975191A

Other languages

English (en)

Norwegian (no)

Other versions

NO975191D0 (no

NO975191L (no

Inventor

Jean Michel Bernardon

Original Assignee

Galderma Rech Dermatologique

Priority date (The priority date 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 date listed.)

1996-03-14

Filing date

1997-11-12

Publication date

2001-07-09

1997-11-12 Application filed by Galderma Rech Dermatologique filed Critical Galderma Rech Dermatologique

1997-11-12 Publication of NO975191D0 publication Critical patent/NO975191D0/no

1998-01-14 Publication of NO975191L publication Critical patent/NO975191L/no

2001-07-09 Publication of NO310456B1 publication Critical patent/NO310456B1/no

Links

150000001875 compounds Chemical class 0.000 title claims abstract description 64
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239000002253 acid Substances 0.000 claims description 21
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208000035475 disorder Diseases 0.000 claims description 18
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 17
229910052757 nitrogen Inorganic materials 0.000 claims description 14
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230000003287 optical effect Effects 0.000 claims description 7
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DJNFLMOYTJKZKV-UHFFFAOYSA-N 2-hydroxy-4-[3-(5,5,8,8-tetramethyl-6,7-dihydronaphthalen-2-yl)prop-1-ynyl]benzoic acid Chemical compound C=1C=C2C(C)(C)CCC(C)(C)C2=CC=1CC#CC1=CC=C(C(O)=O)C(O)=C1 DJNFLMOYTJKZKV-UHFFFAOYSA-N 0.000 claims description 5
CAONILRKRRLMTN-UHFFFAOYSA-N 4-[3-(5,5,8,8-tetramethyl-6,7-dihydronaphthalen-2-yl)prop-1-ynyl]benzoic acid Chemical compound C=1C=C2C(C)(C)CCC(C)(C)C2=CC=1CC#CC1=CC=C(C(O)=O)C=C1 CAONILRKRRLMTN-UHFFFAOYSA-N 0.000 claims description 5
KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 claims description 5
230000002500 effect on skin Effects 0.000 claims description 5
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PSRULIKUPYGMLW-UHFFFAOYSA-N 4-[3-(3,5-ditert-butyl-4-oxocyclohexa-2,5-dien-1-ylidene)prop-1-ynyl]-2-hydroxybenzoic acid Chemical compound C1=C(C(C)(C)C)C(=O)C(C(C)(C)C)=CC1=CC#CC1=CC=C(C(O)=O)C(O)=C1 PSRULIKUPYGMLW-UHFFFAOYSA-N 0.000 claims description 4
IAUNPOSUGPOYIS-UHFFFAOYSA-N 4-[3-(3,5-ditert-butyl-4-oxocyclohexa-2,5-dien-1-ylidene)prop-1-ynyl]benzoic acid Chemical compound C1=C(C(C)(C)C)C(=O)C(C(C)(C)C)=CC1=CC#CC1=CC=C(C(O)=O)C=C1 IAUNPOSUGPOYIS-UHFFFAOYSA-N 0.000 claims description 4
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PAXLYUGRMZGNOY-UHFFFAOYSA-N 1,1,4,4-tetramethyl-6-[3-(4-methylphenyl)prop-2-ynyl]-2,3-dihydronaphthalene Chemical compound C1=CC(C)=CC=C1C#CCC1=CC=C2C(C)(C)CCC(C)(C)C2=C1 PAXLYUGRMZGNOY-UHFFFAOYSA-N 0.000 claims description 3
MQTYXVOQSUQPPA-UHFFFAOYSA-N 3-methyl-4-[3-(5,5,8,8-tetramethyl-6,7-dihydronaphthalen-2-yl)prop-1-ynyl]benzoic acid Chemical compound CC1=CC(C(O)=O)=CC=C1C#CCC1=CC=C2C(C)(C)CCC(C)(C)C2=C1 MQTYXVOQSUQPPA-UHFFFAOYSA-N 0.000 claims description 3
VPGVGHNLHIFMRQ-UHFFFAOYSA-N 4-[3-(3,5-ditert-butyl-4-hydroxyphenyl)prop-1-ynyl]-2-hydroxybenzoic acid Chemical compound CC(C)(C)C1=C(O)C(C(C)(C)C)=CC(CC#CC=2C=C(O)C(C(O)=O)=CC=2)=C1 VPGVGHNLHIFMRQ-UHFFFAOYSA-N 0.000 claims description 3
RELMMGJCXHRZGV-UHFFFAOYSA-N 4-[3-(4,4-dimethyl-2,3-dihydrothiochromen-6-yl)prop-1-ynyl]-2-hydroxybenzoic acid Chemical compound C1=C2C(C)(C)CCSC2=CC=C1CC#CC1=CC=C(C(O)=O)C(O)=C1 RELMMGJCXHRZGV-UHFFFAOYSA-N 0.000 claims description 3
NJZNKCASUWILKP-UHFFFAOYSA-N 4-[3-(5,5,8,8-tetramethyl-6,7-dihydronaphthalen-2-yl)prop-1-ynyl]benzaldehyde Chemical compound C=1C=C2C(C)(C)CCC(C)(C)C2=CC=1CC#CC1=CC=C(C=O)C=C1 NJZNKCASUWILKP-UHFFFAOYSA-N 0.000 claims description 3
HXPSEDKGMHDEAQ-UHFFFAOYSA-N 4-[3-(5,5,8,8-tetramethyl-6,7-dihydronaphthalen-2-yl)prop-1-ynyl]benzamide Chemical compound C=1C=C2C(C)(C)CCC(C)(C)C2=CC=1CC#CC1=CC=C(C(N)=O)C=C1 HXPSEDKGMHDEAQ-UHFFFAOYSA-N 0.000 claims description 3
BNHOTZZGTUMSMC-UHFFFAOYSA-N 4-[3-(5,5,8,8-tetramethyl-6,7-dihydronaphthalen-2-yl)prop-1-ynyl]phenol Chemical compound C=1C=C2C(C)(C)CCC(C)(C)C2=CC=1CC#CC1=CC=C(O)C=C1 BNHOTZZGTUMSMC-UHFFFAOYSA-N 0.000 claims description 3
MOLTYSBHBHPNBM-UHFFFAOYSA-N 4-[3-(5,5,8,8-tetramethyl-6,7-dihydronaphthalen-2-yl)prop-2-ynyl]benzoic acid Chemical compound C=1C=C2C(C)(C)CCC(C)(C)C2=CC=1C#CCC1=CC=C(C(O)=O)C=C1 MOLTYSBHBHPNBM-UHFFFAOYSA-N 0.000 claims description 3
ASDAIPPBVOUDRJ-UHFFFAOYSA-N 4-[3-(5,5,8,8-tetramethyl-6,7-dihydronaphthalen-2-yl)propa-1,2-dienyl]benzoic acid Chemical compound C=1C=C2C(C)(C)CCC(C)(C)C2=CC=1C=C=CC1=CC=C(C(O)=O)C=C1 ASDAIPPBVOUDRJ-UHFFFAOYSA-N 0.000 claims description 3
CYMMIHHPSDDDAT-UHFFFAOYSA-N 4-[3-(8,8-dimethyl-6,7-dihydro-5h-naphthalen-2-yl)prop-1-ynyl]-2-hydroxybenzoic acid Chemical compound C1=C2C(C)(C)CCCC2=CC=C1CC#CC1=CC=C(C(O)=O)C(O)=C1 CYMMIHHPSDDDAT-UHFFFAOYSA-N 0.000 claims description 3
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XOIOHXLMOGZBTK-UHFFFAOYSA-N methyl 2-hydroxy-4-[3-(5,5,8,8-tetramethyl-6,7-dihydronaphthalen-2-yl)prop-1-ynyl]benzoate Chemical compound C1=C(O)C(C(=O)OC)=CC=C1C#CCC1=CC=C2C(C)(C)CCC(C)(C)C2=C1 XOIOHXLMOGZBTK-UHFFFAOYSA-N 0.000 claims description 3
AXTUWDSYBGALNY-UHFFFAOYSA-N morpholin-4-yl-[4-[3-(5,5,8,8-tetramethyl-6,7-dihydronaphthalen-2-yl)prop-1-ynyl]phenyl]methanone Chemical compound C=1C=C2C(C)(C)CCC(C)(C)C2=CC=1CC#CC(C=C1)=CC=C1C(=O)N1CCOCC1 AXTUWDSYBGALNY-UHFFFAOYSA-N 0.000 claims description 3
QPVIBEFVEZQTNA-UHFFFAOYSA-N n,2-dihydroxy-4-[3-(5,5,8,8-tetramethyl-6,7-dihydronaphthalen-2-yl)prop-1-ynyl]benzamide Chemical compound C=1C=C2C(C)(C)CCC(C)(C)C2=CC=1CC#CC1=CC=C(C(=O)NO)C(O)=C1 QPVIBEFVEZQTNA-UHFFFAOYSA-N 0.000 claims description 3
BHKGHKQUVDWCEW-UHFFFAOYSA-N n-(4-hydroxyphenyl)-4-[3-(5,5,8,8-tetramethyl-6,7-dihydronaphthalen-2-yl)prop-1-ynyl]benzamide Chemical compound C=1C=C2C(C)(C)CCC(C)(C)C2=CC=1CC#CC(C=C1)=CC=C1C(=O)NC1=CC=C(O)C=C1 BHKGHKQUVDWCEW-UHFFFAOYSA-N 0.000 claims description 3
208000008742 seborrheic dermatitis Diseases 0.000 claims description 3
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IWIZJAWWAKXRFO-UHFFFAOYSA-N 2-(2-hydroxyethylamino)ethanol;2-hydroxy-4-[3-(5,5,8,8-tetramethyl-6,7-dihydronaphthalen-2-yl)prop-1-ynyl]benzoic acid Chemical compound OCCNCCO.C=1C=C2C(C)(C)CCC(C)(C)C2=CC=1CC#CC1=CC=C(C(O)=O)C(O)=C1 IWIZJAWWAKXRFO-UHFFFAOYSA-N 0.000 claims description 2
KWJUTWGBVVTMGJ-UHFFFAOYSA-N 2-(hydroxymethyl)-5-[3-(5,5,8,8-tetramethyl-6,7-dihydronaphthalen-2-yl)prop-1-ynyl]phenol Chemical compound C=1C=C2C(C)(C)CCC(C)(C)C2=CC=1CC#CC1=CC=C(CO)C(O)=C1 KWJUTWGBVVTMGJ-UHFFFAOYSA-N 0.000 claims description 2
SOQDUJOCQBARMJ-UHFFFAOYSA-N 2-hydroxy-4-[3-(3-hydroxy-5,5,8,8-tetramethyl-6,7-dihydronaphthalen-2-yl)prop-1-ynyl]benzoic acid Chemical compound OC=1C=C2C(C)(C)CCC(C)(C)C2=CC=1CC#CC1=CC=C(C(O)=O)C(O)=C1 SOQDUJOCQBARMJ-UHFFFAOYSA-N 0.000 claims description 2
YXGFOGWKMBYZSI-UHFFFAOYSA-N 2-hydroxy-4-[3-(5,5,8,8-tetramethyl-6,7-dihydronaphthalen-2-yl)but-1-ynyl]benzoic acid Chemical compound C=1C=C(C(CCC2(C)C)(C)C)C2=CC=1C(C)C#CC1=CC=C(C(O)=O)C(O)=C1 YXGFOGWKMBYZSI-UHFFFAOYSA-N 0.000 claims description 2
ZIYQHTVGGPXOCM-UHFFFAOYSA-N 2-hydroxy-4-[3-(5,5,8,8-tetramethyl-6,7-dihydronaphthalen-2-yl)propa-1,2-dienyl]benzoic acid Chemical compound C=1C=C2C(C)(C)CCC(C)(C)C2=CC=1C=C=CC1=CC=C(C(O)=O)C(O)=C1 ZIYQHTVGGPXOCM-UHFFFAOYSA-N 0.000 claims description 2
XHHJYZIGLXQXMR-UHFFFAOYSA-N 2-methyl-4-[3-(5,5,8,8-tetramethyl-6,7-dihydronaphthalen-2-yl)prop-1-ynyl]benzoic acid Chemical compound C1=C(C(O)=O)C(C)=CC(C#CCC=2C=C3C(C(CCC3(C)C)(C)C)=CC=2)=C1 XHHJYZIGLXQXMR-UHFFFAOYSA-N 0.000 claims description 2
NGFMDJUZDRPHTR-UHFFFAOYSA-N 4-[3-(3,5,5,8,8-pentamethyl-6,7-dihydronaphthalen-2-yl)prop-1-ynyl]benzoic acid Chemical compound CC1=CC(C(CCC2(C)C)(C)C)=C2C=C1CC#CC1=CC=C(C(O)=O)C=C1 NGFMDJUZDRPHTR-UHFFFAOYSA-N 0.000 claims description 2
HKIFTPXSSYHQQW-UHFFFAOYSA-N 4-[3-(3,5-ditert-butyl-4-hydroxyphenyl)prop-1-ynyl]benzoic acid Chemical compound CC(C)(C)C1=C(O)C(C(C)(C)C)=CC(CC#CC=2C=CC(=CC=2)C(O)=O)=C1 HKIFTPXSSYHQQW-UHFFFAOYSA-N 0.000 claims description 2
CXEOFTLVNKPBFL-UHFFFAOYSA-N 4-[3-(3-tert-butyl-4-hydroxyphenyl)prop-1-ynyl]-2-hydroxybenzoic acid Chemical compound C1=C(O)C(C(C)(C)C)=CC(CC#CC=2C=C(O)C(C(O)=O)=CC=2)=C1 CXEOFTLVNKPBFL-UHFFFAOYSA-N 0.000 claims description 2
QPKPTGAJOCKFQQ-UHFFFAOYSA-N 4-[3-(3-tert-butyl-4-methoxyphenyl)prop-1-ynyl]-2-hydroxybenzoic acid Chemical compound C1=C(C(C)(C)C)C(OC)=CC=C1CC#CC1=CC=C(C(O)=O)C(O)=C1 QPKPTGAJOCKFQQ-UHFFFAOYSA-N 0.000 claims description 2
CKINFDLDYSEYOO-UHFFFAOYSA-N 4-[3-(5,5-dimethyl-7,8-dihydro-6h-naphthalen-2-yl)prop-1-ynyl]-2-hydroxybenzoic acid Chemical compound C=1C=C2C(C)(C)CCCC2=CC=1CC#CC1=CC=C(C(O)=O)C(O)=C1 CKINFDLDYSEYOO-UHFFFAOYSA-N 0.000 claims description 2
UDNAUBKRFVUBNO-UHFFFAOYSA-N 5-[3-(5,5,8,8-tetramethyl-6,7-dihydronaphthalen-2-yl)prop-1-ynyl]pyridine-2-carboxylic acid Chemical compound C=1C=C2C(C)(C)CCC(C)(C)C2=CC=1CC#CC1=CC=C(C(O)=O)N=C1 UDNAUBKRFVUBNO-UHFFFAOYSA-N 0.000 claims description 2
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229960002036 phenytoin Drugs 0.000 description 1
229920000642 polymer Polymers 0.000 description 1
LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
239000003755 preservative agent Substances 0.000 description 1
230000001737 promoting effect Effects 0.000 description 1
NCNISYUOWMIOPI-UHFFFAOYSA-N propane-1,1-dithiol Chemical compound CCC(S)S NCNISYUOWMIOPI-UHFFFAOYSA-N 0.000 description 1
125000006239 protecting group Chemical group 0.000 description 1
ZDYVRSLAEXCVBX-UHFFFAOYSA-N pyridinium p-toluenesulfonate Chemical compound C1=CC=[NH+]C=C1.CC1=CC=C(S([O-])(=O)=O)C=C1 ZDYVRSLAEXCVBX-UHFFFAOYSA-N 0.000 description 1
NPCOQXAVBJJZBQ-UHFFFAOYSA-N reduced coenzyme Q9 Natural products COC1=C(O)C(C)=C(CC=C(C)CCC=C(C)CCC=C(C)CCC=C(C)CCC=C(C)CCC=C(C)CCC=C(C)CCC=C(C)CCC=C(C)C)C(O)=C1OC NPCOQXAVBJJZBQ-UHFFFAOYSA-N 0.000 description 1
150000004492 retinoid derivatives Chemical class 0.000 description 1
201000004700 rosacea Diseases 0.000 description 1
SMQUZDBALVYZAC-UHFFFAOYSA-N salicylaldehyde Chemical class OC1=CC=CC=C1C=O SMQUZDBALVYZAC-UHFFFAOYSA-N 0.000 description 1
238000012216 screening Methods 0.000 description 1
239000002453 shampoo Substances 0.000 description 1
230000009759 skin aging Effects 0.000 description 1
230000036555 skin type Effects 0.000 description 1
239000000344 soap Substances 0.000 description 1
235000017557 sodium bicarbonate Nutrition 0.000 description 1
229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
239000012312 sodium hydride Substances 0.000 description 1
229910000104 sodium hydride Inorganic materials 0.000 description 1
239000007921 spray Substances 0.000 description 1
239000003381 stabilizer Substances 0.000 description 1
125000004079 stearyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
208000011580 syndromic disease Diseases 0.000 description 1
239000006188 syrup Substances 0.000 description 1
235000020357 syrup Nutrition 0.000 description 1
239000003826 tablet Substances 0.000 description 1
239000011975 tartaric acid Substances 0.000 description 1
235000002906 tartaric acid Nutrition 0.000 description 1
208000001608 teratocarcinoma Diseases 0.000 description 1
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
235000019364 tetracycline Nutrition 0.000 description 1
150000003522 tetracyclines Chemical class 0.000 description 1
229940040944 tetracyclines Drugs 0.000 description 1
230000001225 therapeutic effect Effects 0.000 description 1
229960000984 tocofersolan Drugs 0.000 description 1
239000011732 tocopherol Substances 0.000 description 1
229960001295 tocopherol Drugs 0.000 description 1
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
229940040064 ubiquinol Drugs 0.000 description 1
QNTNKSLOFHEFPK-UPTCCGCDSA-N ubiquinol-10 Chemical compound COC1=C(O)C(C)=C(C\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CCC=C(C)C)C(O)=C1OC QNTNKSLOFHEFPK-UPTCCGCDSA-N 0.000 description 1
235000013343 vitamin Nutrition 0.000 description 1
229930003231 vitamin Natural products 0.000 description 1
150000003703 vitamin D2 derivatives Chemical class 0.000 description 1
235000005282 vitamin D3 Nutrition 0.000 description 1
239000011647 vitamin D3 Substances 0.000 description 1
QYSXJUFSXHHAJI-YRZJJWOYSA-N vitamin D3 Chemical compound C1(/[C@@H]2CC[C@@H]([C@]2(CCC1)C)[C@H](C)CCCC(C)C)=C\C=C1\C[C@@H](O)CCC1=C QYSXJUFSXHHAJI-YRZJJWOYSA-N 0.000 description 1
229940021056 vitamin d3 Drugs 0.000 description 1
239000000080 wetting agent Substances 0.000 description 1
239000002076 α-tocopherol Substances 0.000 description 1
235000004835 α-tocopherol Nutrition 0.000 description 1
OENHQHLEOONYIE-JLTXGRSLSA-N β-Carotene Chemical compound CC=1CCCC(C)(C)C=1\C=C\C(\C)=C\C=C\C(\C)=C\C=C\C=C(/C)\C=C\C=C(/C)\C=C\C1=C(C)CCCC1(C)C OENHQHLEOONYIE-JLTXGRSLSA-N 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/76—Esters of carboxylic acids having a carboxyl group bound to a carbon atom of a six-membered aromatic ring
- C07C69/94—Esters of carboxylic acids having a carboxyl group bound to a carbon atom of a six-membered aromatic ring of polycyclic hydroxy carboxylic acids, the hydroxy groups and the carboxyl groups of which are bound to carbon atoms of six-membered aromatic rings
- 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
- A61K31/185—Acids; Anhydrides, halides or salts thereof, e.g. sulfur acids, imidic, hydrazonic or hydroximic acids
- A61K31/19—Carboxylic acids, e.g. valproic acid
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
- A61P17/16—Emollients or protectives, e.g. against radiation
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P19/00—Drugs for skeletal disorders
- A61P19/02—Drugs for skeletal disorders for joint disorders, e.g. arthritis, arthrosis
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/12—Antihypertensives
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C13/00—Cyclic hydrocarbons containing rings other than, or in addition to, six-membered aromatic rings
- C07C13/28—Polycyclic hydrocarbons or acyclic hydrocarbon derivatives thereof
- C07C13/32—Polycyclic hydrocarbons or acyclic hydrocarbon derivatives thereof with condensed rings
- C07C13/47—Polycyclic hydrocarbons or acyclic hydrocarbon derivatives thereof with condensed rings with a bicyclo ring system containing ten carbon atoms
- C07C13/48—Completely or partially hydrogenated naphthalenes
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C313/00—Sulfinic acids; Sulfenic acids; Halides, esters or anhydrides thereof; Amides of sulfinic or sulfenic acids, i.e. compounds having singly-bound oxygen atoms of sulfinic or sulfenic groups replaced by nitrogen atoms, not being part of nitro or nitroso groups
- C07C313/02—Sulfinic acids; Derivatives thereof
- C07C313/04—Sulfinic acids; Esters thereof
- 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
- 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
- C07C45/27—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation
- C07C45/29—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation of hydroxy groups
- C07C45/298—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation of hydroxy groups with manganese derivatives
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C63/00—Compounds having carboxyl groups bound to a carbon atoms of six-membered aromatic rings
- C07C63/66—Polycyclic acids with unsaturation outside the aromatic rings
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C65/00—Compounds having carboxyl groups bound to carbon atoms of six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
- C07C65/01—Compounds having carboxyl groups bound to carbon atoms of six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups containing hydroxy or O-metal groups
- C07C65/19—Compounds having carboxyl groups bound to carbon atoms of six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups containing hydroxy or O-metal groups having unsaturation outside the aromatic ring
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C65/00—Compounds having carboxyl groups bound to carbon atoms of six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
- C07C65/32—Compounds having carboxyl groups bound to carbon atoms of six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups containing keto groups
- C07C65/40—Compounds having carboxyl groups bound to carbon atoms of six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups containing keto groups containing singly bound oxygen-containing groups
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/76—Esters of carboxylic acids having a carboxyl group bound to a carbon atom of a six-membered aromatic ring
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D335/00—Heterocyclic compounds containing six-membered rings having one sulfur atom as the only ring hetero atom
- C07D335/04—Heterocyclic compounds containing six-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
- C07D335/06—Benzothiopyrans; Hydrogenated benzothiopyrans
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2602/00—Systems containing two condensed rings
- C07C2602/02—Systems containing two condensed rings the rings having only two atoms in common
- C07C2602/04—One of the condensed rings being a six-membered aromatic ring
- C07C2602/10—One of the condensed rings being a six-membered aromatic ring the other ring being six-membered, e.g. tetraline

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Medicinal Chemistry (AREA)
Pharmacology & Pharmacy (AREA)
Life Sciences & Earth Sciences (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Engineering & Computer Science (AREA)
Bioinformatics & Cheminformatics (AREA)
Dermatology (AREA)
Cardiology (AREA)
Diabetes (AREA)
Rheumatology (AREA)
Heart & Thoracic Surgery (AREA)
Toxicology (AREA)
Orthopedic Medicine & Surgery (AREA)
Urology & Nephrology (AREA)
Obesity (AREA)
Pain & Pain Management (AREA)
Hematology (AREA)
Emergency Medicine (AREA)
Endocrinology (AREA)
Immunology (AREA)
Vascular Medicine (AREA)
Physical Education & Sports Medicine (AREA)
Epidemiology (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)
Pyridine Compounds (AREA)
Cosmetics (AREA)
Heterocyclic Compounds Containing Sulfur Atoms (AREA)
Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)

NO19975191A 1996-03-14 1997-11-12 Diaromatiske dienylforbindelser, farmasöytiske og kosmetiske preparater inneholdende slike forbindelser, samt anvendelse NO310456B1 (no)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
FR9603234A FR2746098B1 (fr)	1996-03-14	1996-03-14	Composes propynyl biaromatiques
PCT/FR1997/000390 WO1997033856A1 (fr)	1996-03-14	1997-03-05	Composes propynyl ou dienyl biaromatiques

Publications (3)

Publication Number	Publication Date
NO975191D0 NO975191D0 (no)	1997-11-12
NO975191L NO975191L (no)	1998-01-14
NO310456B1 true NO310456B1 (no)	2001-07-09

Family

ID=9490194

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NO19975191A NO310456B1 (no)	1996-03-14	1997-11-12	Diaromatiske dienylforbindelser, farmasöytiske og kosmetiske preparater inneholdende slike forbindelser, samt anvendelse

Country Status (21)

Country	Link
US (2)	US6046220A (pl)
EP (1)	EP0832057B1 (pl)
JP (1)	JP3181297B2 (pl)
KR (1)	KR100305340B1 (pl)
CN (3)	CN1079390C (pl)
AT (1)	ATE198467T1 (pl)
AU (1)	AU703505B2 (pl)
BR (1)	BR9702144A (pl)
DE (1)	DE69703820T2 (pl)
DK (1)	DK0832057T3 (pl)
EA (1)	EA001060B1 (pl)
ES (1)	ES2156366T3 (pl)
FR (1)	FR2746098B1 (pl)
GR (1)	GR3035576T3 (pl)
HU (1)	HUP9900624A3 (pl)
IL (1)	IL122195A0 (pl)
MX (1)	MX9708803A (pl)
NO (1)	NO310456B1 (pl)
NZ (1)	NZ329198A (pl)
PL (1)	PL187406B1 (pl)
WO (1)	WO1997033856A1 (pl)

Families Citing this family (17)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
EP0974584B1 (en)	1997-02-21	2003-01-15	Takeda Chemical Industries, Ltd.	Fused ring compounds, process for producing the same and use thereof
FR2764604B1 (fr) *	1997-06-13	1999-09-10	Cird Galderma	Composes bi-aromatiques relies par un radical propynylene ou allenylene et compositions pharmaceutiques et cosmetiques les contenant
FR2801307B1 (fr) *	1999-11-24	2002-12-06	Galderma Res & Dev	Analogues de la vitamine d
CA2407189A1 (en)	2000-05-02	2001-11-08	F. Hoffmann-La Roche Ag	New gamma selective retinoids
JP4118675B2 (ja)	2000-10-02	2008-07-16	エフ．ホフマン−ラロシュアーゲー	気腫治療用新規レチノイド
ATE360010T1 (de) *	2001-10-31	2007-05-15	Hoffmann La Roche	Heterocyclische retioidverbindungen
AU2003240633A1 (en) *	2002-04-25	2003-11-10	Galderma Research And Development, S.N.C.	Process for the enantioselective synthesis of propargyl alcohol derivatives of r configuration from the racemic mixtures thereof
TW200418825A (en) *	2002-12-16	2004-10-01	Hoffmann La Roche	Novel (R)-and (S) enantiomers of thiophene hydroxamic acid derivatives
DE602004021288D1 (de)	2003-12-08	2009-07-09	Galderma Res & Dev	Neue liganden, bei denen es sich um aktivatoren des rar-rezeptors handelt, verwendung in der humanmedizin und in kosmetika
EP1541549A1 (en) *	2003-12-12	2005-06-15	Exonhit Therapeutics S.A.	Tricyclic hydroxamate and benzaminde derivatives, compositions and methods
FR2910320B1 (fr)	2006-12-21	2009-02-13	Galderma Res & Dev S N C Snc	Emulsion comprenant au moins un retinoide et du peroxyde de benzole
FR2910321B1 (fr)	2006-12-21	2009-07-10	Galderma Res & Dev S N C Snc	Gel creme comprenant au moins un retinoide et du peroxyde de benzole
FR2931661B1 (fr)	2008-05-30	2010-07-30	Galderma Res & Dev	Nouvelles compositions depigmentantes sous forme d'une composition anhydre sans vaseline et sans elastomere comprenant un derive phenolique solubilise et un retinoide.
JP5155244B2 (ja) *	2009-04-21	2013-03-06	株式会社Ａｄｅｋａ	細胞培養基板
US8884038B2 (en) *	2011-06-13	2014-11-11	Nalco Company	Synthesis of 7-acetyleno quinone methide derivatives and their application as vinylic polymerization retarders
RU2753863C2 (ru)	2016-02-03	2021-08-24	Галдерма Ресерч Энд Девелопмент	Новые биароматические соединения пропинила, фармацевтические и косметические композиции, их содержащие, и их применение
EP3923435B1 (de)	2020-06-10	2025-03-19	HSP Hochspannungsgeräte GmbH	Verfahren und eine vorrichtung zur überwachung eines kompensiert betriebenen drehstromnetzes auf eine abstimmungsänderung der erdschlusslöschspule

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Publication number	Priority date	Publication date	Assignee	Title
US5264578A (en) *	1987-03-20	1993-11-23	Allergan, Inc.	Disubstituted acetylenes bearing heterobicyclic groups and heteroaromatic or phenyl groups having retinoid like activity
CA2093577C (en) *	1992-05-07	2006-01-03	Michael Klaus	Alkyl or alkoxy substituted s-heterocyclic retinoids
US5466861A (en) *	1992-11-25	1995-11-14	Sri International	Bridged bicyclic aromatic compounds and their use in modulating gene expression of retinoid receptors
US5455265A (en) *	1993-02-11	1995-10-03	Allergan, Inc.	Method of treatment with compounds having selective agonist-like activity on RXR retinoid receptors
FR2713635B1 (fr) *	1993-12-15	1996-01-05	Cird Galderma	Nouveaux composés propynyl bi-aromatiques, compositions pharmaceutiques et cosmétiques les contenant et utilisations.
DE4402915A1 (de)	1994-02-01	1995-08-03	Bayer Ag	Verfahren zur Herstellung von 3-Aryl-propinen

1996
- 1996-03-14 FR FR9603234A patent/FR2746098B1/fr not_active Expired - Fee Related
1997
- 1997-03-05 CN CN97190539A patent/CN1079390C/zh not_active Expired - Fee Related
- 1997-03-05 NZ NZ329198A patent/NZ329198A/xx unknown
- 1997-03-05 IL IL12219597A patent/IL122195A0/xx unknown
- 1997-03-05 ES ES97908307T patent/ES2156366T3/es not_active Expired - Lifetime
- 1997-03-05 BR BR9702144A patent/BR9702144A/pt active Search and Examination
- 1997-03-05 PL PL97323363A patent/PL187406B1/pl not_active IP Right Cessation
- 1997-03-05 AU AU20304/97A patent/AU703505B2/en not_active Ceased
- 1997-03-05 CN CNA2004100119214A patent/CN1670009A/zh active Pending
- 1997-03-05 EA EA199700381A patent/EA001060B1/ru not_active IP Right Cessation
- 1997-03-05 US US08/952,302 patent/US6046220A/en not_active Expired - Fee Related
- 1997-03-05 KR KR1019970708147A patent/KR100305340B1/ko not_active Expired - Fee Related
- 1997-03-05 WO PCT/FR1997/000390 patent/WO1997033856A1/fr not_active Ceased
- 1997-03-05 DE DE69703820T patent/DE69703820T2/de not_active Expired - Fee Related
- 1997-03-05 JP JP53231797A patent/JP3181297B2/ja not_active Expired - Fee Related
- 1997-03-05 EP EP97908307A patent/EP0832057B1/fr not_active Expired - Lifetime
- 1997-03-05 DK DK97908307T patent/DK0832057T3/da active
- 1997-03-05 MX MX9708803A patent/MX9708803A/es not_active IP Right Cessation
- 1997-03-05 AT AT97908307T patent/ATE198467T1/de not_active IP Right Cessation
- 1997-03-05 HU HU9900624A patent/HUP9900624A3/hu unknown
- 1997-11-12 NO NO19975191A patent/NO310456B1/no not_active IP Right Cessation
1999
- 1999-12-17 US US09/466,230 patent/US6313162B1/en not_active Expired - Fee Related
2001
- 2001-03-14 GR GR20010400423T patent/GR3035576T3/el not_active IP Right Cessation
- 2001-10-26 CN CNB01135853XA patent/CN1213017C/zh not_active Expired - Fee Related

Also Published As

Publication number	Publication date
JP3181297B2 (ja)	2001-07-03
HUP9900624A2 (hu)	1999-07-28
ES2156366T3 (es)	2001-06-16
FR2746098A1 (fr)	1997-09-19
DK0832057T3 (da)	2001-02-26
NO975191D0 (no)	1997-11-12
KR19990014803A (ko)	1999-02-25
EA001060B1 (ru)	2000-10-30
IL122195A0 (en)	1998-04-05
DE69703820T2 (de)	2001-04-26
DE69703820D1 (de)	2001-02-08
AU2030497A (en)	1997-10-01
EP0832057A1 (fr)	1998-04-01
FR2746098B1 (fr)	1998-04-30
ATE198467T1 (de)	2001-01-15
PL323363A1 (en)	1998-03-30
WO1997033856A1 (fr)	1997-09-18
EA199700381A1 (ru)	1998-06-25
CN1213017C (zh)	2005-08-03
CN1376664A (zh)	2002-10-30
CN1079390C (zh)	2002-02-20
PL187406B1 (pl)	2004-07-30
US6046220A (en)	2000-04-04
GR3035576T3 (en)	2001-06-29
CN1193313A (zh)	1998-09-16
NO975191L (no)	1998-01-14
US6313162B1 (en)	2001-11-06
BR9702144A (pt)	1999-01-05
EP0832057B1 (fr)	2001-01-03
JPH10510849A (ja)	1998-10-20
CN1670009A (zh)	2005-09-21
HUP9900624A3 (en)	2000-09-28
AU703505B2 (en)	1999-03-25
MX9708803A (es)	1998-02-28
KR100305340B1 (ko)	2001-10-19
NZ329198A (en)	1999-08-30

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Publication	Publication Date	Title
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US20030135053A1 (en)	2003-07-17	Bicyclic aromatic compounds
US5574036A (en)	1996-11-12	Adamantyl-substituted polycyclic acetylene compounds and pharmaceutical/cosmetic compositions comprised thereof
US5981776A (en)	1999-11-09	Heterocyclic biaryl compounds, pharmaceutical and cosmetic compositions containing them and uses thereof
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US6326510B1 (en)	2001-12-04	Bi-aromatic compounds, compositions containing them and uses
AU717195B2 (en)	2000-03-23	Novel biaromatic dibenzofuran derivatives and their use in human or veterinary medicine and in cosmetics
KR100300380B1 (ko)	2001-09-22	이 방향족 프로피닐 화합물
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MXPA00012229A (en)	2002-05-09	Diarylselenide compounds and their use in human or veterinary medicine and in cosmetics
NZ331458A (en)	2001-05-25	Use of 7-Adamantyl-naphth-2-yl(hetero)aryl carboxylic acids, derivatives thereof (retinoid analogues) in preparing medicaments; compounds having a polyether radical bound to a moiety of at least two carbon atoms in position-beta