NL7905893A - Werkwijze voor de bereiding van retinoiden en de toepassing daarvan ter voorkoming van carcinogenese. - Google Patents

Werkwijze voor de bereiding van retinoiden en de toepassing daarvan ter voorkoming van carcinogenese. Download PDF

Info

Publication number: NL7905893A
Authority: NL; Netherlands
Prior art keywords: retinamide; trans; total; retinoids; prevention
Prior art date: 1978-07-31

Application number

NL7905893A

Other languages

English (en)

Dutch (nl)

Original Assignee

Johnson & Johnson

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.)

1978-07-31

Filing date

1979-07-31

Publication date

1980-02-04

1979-07-31 Application filed by Johnson & Johnson filed Critical Johnson & Johnson

1980-02-04 Publication of NL7905893A publication Critical patent/NL7905893A/nl

Links

238000000034 method Methods 0.000 title claims description 11
208000005623 Carcinogenesis Diseases 0.000 title claims description 10
230000002265 prevention Effects 0.000 title claims description 10
230000008569 process Effects 0.000 title claims description 8
238000002360 preparation method Methods 0.000 title claims description 6
229940100552 retinamide Drugs 0.000 claims description 16
-1 4-butyryloxyphenyl Chemical group 0.000 claims description 9
230000036952 cancer formation Effects 0.000 claims description 9
231100000504 carcinogenesis Toxicity 0.000 claims description 9
210000000981 epithelium Anatomy 0.000 claims description 9
239000003795 chemical substances by application Substances 0.000 claims 1
239000008194 pharmaceutical composition Substances 0.000 claims 1
239000000825 pharmaceutical preparation Substances 0.000 claims 1
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 12
201000009030 Carcinoma Diseases 0.000 description 11
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 11
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
239000011541 reaction mixture Substances 0.000 description 8
206010054949 Metaplasia Diseases 0.000 description 7
230000015689 metaplastic ossification Effects 0.000 description 7
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
230000000694 effects Effects 0.000 description 6
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 6
QGNJRVVDBSJHIZ-QHLGVNSISA-N retinyl acetate Chemical compound CC(=O)OC\C=C(/C)\C=C\C=C(/C)\C=C\C1=C(C)CCCC1(C)C QGNJRVVDBSJHIZ-QHLGVNSISA-N 0.000 description 6
241000124008 Mammalia Species 0.000 description 5
206010028980 Neoplasm Diseases 0.000 description 5
SHGAZHPCJJPHSC-YCNIQYBTSA-N all-trans-retinoic acid Chemical compound OC(=O)\C=C(/C)\C=C\C=C(/C)\C=C\C1=C(C)CCCC1(C)C SHGAZHPCJJPHSC-YCNIQYBTSA-N 0.000 description 5
FPIPGXGPPPQFEQ-OVSJKPMPSA-N all-trans-retinol Chemical compound OC\C=C(/C)\C=C\C=C(/C)\C=C\C1=C(C)CCCC1(C)C FPIPGXGPPPQFEQ-OVSJKPMPSA-N 0.000 description 5
201000011510 cancer Diseases 0.000 description 5
239000012153 distilled water Substances 0.000 description 5
239000012071 phase Substances 0.000 description 5
229930002330 retinoic acid Natural products 0.000 description 5
210000003437 trachea Anatomy 0.000 description 5
229960001727 tretinoin Drugs 0.000 description 5
210000003932 urinary bladder Anatomy 0.000 description 5
FPIPGXGPPPQFEQ-UHFFFAOYSA-N 13-cis retinol Natural products OCC=C(C)C=CC=C(C)C=CC1=C(C)CCCC1(C)C FPIPGXGPPPQFEQ-UHFFFAOYSA-N 0.000 description 4
125000004203 4-hydroxyphenyl group Chemical group [H]OC1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 4
102000011782 Keratins Human genes 0.000 description 4
108010076876 Keratins Proteins 0.000 description 4
241000700159 Rattus Species 0.000 description 4
238000011161 development Methods 0.000 description 4
230000018109 developmental process Effects 0.000 description 4
201000010099 disease Diseases 0.000 description 4
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 4
229910052757 nitrogen Inorganic materials 0.000 description 4
239000012265 solid product Substances 0.000 description 4
238000012360 testing method Methods 0.000 description 4
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
101100334117 Caenorhabditis elegans fah-1 gene Proteins 0.000 description 3
SHGAZHPCJJPHSC-NUEINMDLSA-N Isotretinoin Chemical compound OC(=O)C=C(C)/C=C/C=C(C)C=CC1=C(C)CCCC1(C)C SHGAZHPCJJPHSC-NUEINMDLSA-N 0.000 description 3
239000002253 acid Substances 0.000 description 3
239000008346 aqueous phase Substances 0.000 description 3
230000015572 biosynthetic process Effects 0.000 description 3
210000000481 breast Anatomy 0.000 description 3
230000004069 differentiation Effects 0.000 description 3
229960005280 isotretinoin Drugs 0.000 description 3
238000002844 melting Methods 0.000 description 3
230000008018 melting Effects 0.000 description 3
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
210000000056 organ Anatomy 0.000 description 3
239000000047 product Substances 0.000 description 3
238000011160 research Methods 0.000 description 3
150000004492 retinoid derivatives Chemical class 0.000 description 3
229960000342 retinol acetate Drugs 0.000 description 3
235000019173 retinyl acetate Nutrition 0.000 description 3
239000011770 retinyl acetate Substances 0.000 description 3
238000001228 spectrum Methods 0.000 description 3
239000000126 substance Substances 0.000 description 3
206010006187 Breast cancer Diseases 0.000 description 2
208000026310 Breast neoplasm Diseases 0.000 description 2
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
VYGQUTWHTHXGQB-FFHKNEKCSA-N Retinol Palmitate Chemical compound CCCCCCCCCCCCCCCC(=O)OC\C=C(/C)\C=C\C=C(/C)\C=C\C1=C(C)CCCC1(C)C VYGQUTWHTHXGQB-FFHKNEKCSA-N 0.000 description 2
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
FPIPGXGPPPQFEQ-BOOMUCAASA-N Vitamin A Natural products OC/C=C(/C)\C=C\C=C(\C)/C=C/C1=C(C)CCCC1(C)C FPIPGXGPPPQFEQ-BOOMUCAASA-N 0.000 description 2
230000002159 abnormal effect Effects 0.000 description 2
150000001408 amides Chemical class 0.000 description 2
230000033228 biological regulation Effects 0.000 description 2
239000003183 carcinogenic agent Substances 0.000 description 2
230000024245 cell differentiation Effects 0.000 description 2
238000006243 chemical reaction Methods 0.000 description 2
210000001072 colon Anatomy 0.000 description 2
150000001875 compounds Chemical class 0.000 description 2
238000002474 experimental method Methods 0.000 description 2
230000003902 lesion Effects 0.000 description 2
231100001231 less toxic Toxicity 0.000 description 2
210000004072 lung Anatomy 0.000 description 2
238000004519 manufacturing process Methods 0.000 description 2
210000000496 pancreas Anatomy 0.000 description 2
239000002244 precipitate Substances 0.000 description 2
230000008439 repair process Effects 0.000 description 2
229960003471 retinol Drugs 0.000 description 2
235000020944 retinol Nutrition 0.000 description 2
239000011607 retinol Substances 0.000 description 2
125000000946 retinyl group Chemical group [H]C([*])([H])/C([H])=C(C([H])([H])[H])/C([H])=C([H])/C([H])=C(C([H])([H])[H])/C([H])=C([H])/C1=C(C([H])([H])[H])C([H])([H])C([H])([H])C([H])([H])C1(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
229910052938 sodium sulfate Inorganic materials 0.000 description 2
235000011152 sodium sulphate Nutrition 0.000 description 2
239000007787 solid Substances 0.000 description 2
238000003756 stirring Methods 0.000 description 2
CMJCEVKJYRZMIA-UHFFFAOYSA-M thallium(i) iodide Chemical compound [Tl]I CMJCEVKJYRZMIA-UHFFFAOYSA-M 0.000 description 2
231100000419 toxicity Toxicity 0.000 description 2
230000001988 toxicity Effects 0.000 description 2
235000019155 vitamin A Nutrition 0.000 description 2
239000011719 vitamin A Substances 0.000 description 2
229940045997 vitamin a Drugs 0.000 description 2
SXIFAEWFOJETOA-UHFFFAOYSA-N 4-hydroxy-butyl Chemical group [CH2]CCCO SXIFAEWFOJETOA-UHFFFAOYSA-N 0.000 description 1
102100022108 Aspartyl/asparaginyl beta-hydroxylase Human genes 0.000 description 1
239000004215 Carbon black (E152) Substances 0.000 description 1
101000901030 Homo sapiens Aspartyl/asparaginyl beta-hydroxylase Proteins 0.000 description 1
238000012404 In vitro experiment Methods 0.000 description 1
206010058467 Lung neoplasm malignant Diseases 0.000 description 1
241001465754 Metazoa Species 0.000 description 1
230000002378 acidificating effect Effects 0.000 description 1
230000009471 action Effects 0.000 description 1
238000013459 approach Methods 0.000 description 1
230000004071 biological effect Effects 0.000 description 1
210000000621 bronchi Anatomy 0.000 description 1
YHASWHZGWUONAO-UHFFFAOYSA-N butanoyl butanoate Chemical compound CCCC(=O)OC(=O)CCC YHASWHZGWUONAO-UHFFFAOYSA-N 0.000 description 1
231100000357 carcinogen Toxicity 0.000 description 1
230000001413 cellular effect Effects 0.000 description 1
230000002113 chemopreventative effect Effects 0.000 description 1
238000001816 cooling Methods 0.000 description 1
238000011393 cytotoxic chemotherapy Methods 0.000 description 1
230000034994 death Effects 0.000 description 1
231100000517 death Toxicity 0.000 description 1
230000003247 decreasing effect Effects 0.000 description 1
235000005911 diet Nutrition 0.000 description 1
230000000378 dietary effect Effects 0.000 description 1
210000002919 epithelial cell Anatomy 0.000 description 1
239000001963 growth medium Substances 0.000 description 1
229930195733 hydrocarbon Natural products 0.000 description 1
206010020718 hyperplasia Diseases 0.000 description 1
230000002390 hyperplastic effect Effects 0.000 description 1
239000003112 inhibitor Substances 0.000 description 1
230000005764 inhibitory process Effects 0.000 description 1
210000000936 intestine Anatomy 0.000 description 1
210000003734 kidney Anatomy 0.000 description 1
231100000053 low toxicity Toxicity 0.000 description 1
201000005202 lung cancer Diseases 0.000 description 1
208000020816 lung neoplasm Diseases 0.000 description 1
230000036210 malignancy Effects 0.000 description 1
230000003211 malignant effect Effects 0.000 description 1
235000012054 meals Nutrition 0.000 description 1
230000007246 mechanism Effects 0.000 description 1
230000010534 mechanism of action Effects 0.000 description 1
239000002609 medium Substances 0.000 description 1
230000004060 metabolic process Effects 0.000 description 1
239000000203 mixture Substances 0.000 description 1
230000000051 modifying effect Effects 0.000 description 1
XKLJHFLUAHKGGU-UHFFFAOYSA-N nitrous amide Chemical compound ON=N XKLJHFLUAHKGGU-UHFFFAOYSA-N 0.000 description 1
239000012074 organic phase Substances 0.000 description 1
210000001672 ovary Anatomy 0.000 description 1
210000000277 pancreatic duct Anatomy 0.000 description 1
230000000144 pharmacologic effect Effects 0.000 description 1
230000001855 preneoplastic effect Effects 0.000 description 1
WYVAMUWZEOHJOQ-UHFFFAOYSA-N propionic anhydride Chemical compound CCC(=O)OC(=O)CC WYVAMUWZEOHJOQ-UHFFFAOYSA-N 0.000 description 1
210000002307 prostate Anatomy 0.000 description 1
108090000623 proteins and genes Proteins 0.000 description 1
102000004169 proteins and genes Human genes 0.000 description 1
230000005855 radiation Effects 0.000 description 1
210000001525 retina Anatomy 0.000 description 1
230000002207 retinal effect Effects 0.000 description 1
229940108325 retinyl palmitate Drugs 0.000 description 1
235000019172 retinyl palmitate Nutrition 0.000 description 1
239000011769 retinyl palmitate Substances 0.000 description 1
230000002441 reversible effect Effects 0.000 description 1
210000003491 skin Anatomy 0.000 description 1
210000002784 stomach Anatomy 0.000 description 1
238000001356 surgical procedure Methods 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
231100000057 systemic toxicity Toxicity 0.000 description 1
210000001550 testis Anatomy 0.000 description 1
231100000331 toxic Toxicity 0.000 description 1
230000002588 toxic effect Effects 0.000 description 1
210000004291 uterus Anatomy 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C403/00—Derivatives of cyclohexane or of a cyclohexene or of cyclohexadiene, having a side-chain containing an acyclic unsaturated part of at least four carbon atoms, this part being directly attached to the cyclohexane or cyclohexene or cyclohexadiene rings, e.g. vitamin A, beta-carotene, beta-ionone
- C07C403/20—Derivatives of cyclohexane or of a cyclohexene or of cyclohexadiene, having a side-chain containing an acyclic unsaturated part of at least four carbon atoms, this part being directly attached to the cyclohexane or cyclohexene or cyclohexadiene rings, e.g. vitamin A, beta-carotene, beta-ionone having side-chains substituted by carboxyl groups or halides, anhydrides, or (thio)esters thereof
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B2200/00—Indexing scheme relating to specific properties of organic compounds
- C07B2200/09—Geometrical isomers
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
- C07C2601/16—Systems containing only non-condensed rings with a six-membered ring the ring being unsaturated

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (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)

NL7905893A 1978-07-31 1979-07-31 Werkwijze voor de bereiding van retinoiden en de toepassing daarvan ter voorkoming van carcinogenese. NL7905893A (nl)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US05/929,093 US4310546A (en)	1978-07-31	1978-07-31	Novel retinoids and their use in preventing carcinogenesis
US92909378		1978-07-31

Publications (1)

Publication Number	Publication Date
NL7905893A true NL7905893A (nl)	1980-02-04

Family

ID=25457311

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NL7905893A NL7905893A (nl)	1978-07-31	1979-07-31	Werkwijze voor de bereiding van retinoiden en de toepassing daarvan ter voorkoming van carcinogenese.

Country Status (14)

Country	Link
US (1)	US4310546A (de)
AT (1)	AT367032B (de)
BE (1)	BE877976A (de)
CA (1)	CA1108170A (de)
CH (1)	CH644845A5 (de)
DE (1)	DE2930923A1 (de)
DK (1)	DK324279A (de)
FR (1)	FR2432509A1 (de)
GB (1)	GB2026493B (de)
IE (1)	IE48304B1 (de)
IT (1)	IT1162414B (de)
NL (1)	NL7905893A (de)
NO (1)	NO149999C (de)
SE (1)	SE442011B (de)

Families Citing this family (17)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US5456663A (en) *	1984-05-25	1995-10-10	Lemelson; Jerome H.	Drugs and methods for treating diseases
US4665098A (en) *	1985-03-28	1987-05-12	Mcneilab, Inc.	Pharmaceutical composition of N-(4-hydroxyphenyl) retinamide having increased bioavailability
EP0321362B1 (de) *	1987-12-16	1996-09-25	Institut Pasteur	Retinoesäurerezeptor und Derivate davon, beide Substanzen codierende DNS und die Verwendung der Proteine und der DNS
US5235076A (en) *	1991-05-28	1993-08-10	University Of Hawaii	Azulenic retinoid compounds, compositions and methods
US5849595A (en) *	1992-10-05	1998-12-15	Alfano; Robert R.	Method for monitoring the effects of chemotherapeutic agents on neoplasmic media
US5716982A (en) *	1995-06-07	1998-02-10	Institute Of Materia Medica, An Institute Of The Chinese Academy Of Medical Sciences	Retinoids and methods of use of same
US5703130A (en) *	1995-06-07	1997-12-30	Institute Of Materia Medica, An Institute Of The Chinese Academy Of Medical Sciences	Chalcone retinoids and methods of use of same
US5968940A (en) *	1995-06-08	1999-10-19	Institute Of Materia Medica	Retinoids and methods of use of same
KR100508627B1 (ko) *	2001-05-29	2005-08-17	(주)케비젠	신규한 레티노이드 유도체 및 이의 제조방법 및 그화합물을 함유한 항암제 조성물
JP2004526807A (ja) *	2001-05-29	2004-09-02	ケビジェンカンパニーリミテッド	新規のレチノイド誘導体及びその製造方法並びにその化合物を含有する抗癌剤組成物
US20070258970A1 (en) *	2003-12-09	2007-11-08	Robert Blumenthal	Methods for Inhibiting Hiv and Other Viral Infections by Modulating Ceramide Metabolism
EP1722766A2 (de) *	2004-02-17	2006-11-22	President And Fellows Of Harvard College	Behandlung von augenerkrankungen einschliesslich makulardegeneration
US7566808B2 (en)	2004-02-17	2009-07-28	President And Fellows Of Harvard College	Management of ophthalmologic disorders, including macular degeneration
CA2638753A1 (en)	2004-12-08	2006-06-15	Sirion Therapeutics, Inc.	Methods, assays and compositions for treating retinol-related diseases
KR20060094745A (ko) *	2005-02-25	2006-08-30	(주)나노하이브리드	층상형 금속 수산화물과 레티노익산의 혼성체를 함유하는암치료용 약학적 조성물
TW200829269A (en) *	2007-01-12	2008-07-16	Koyo Internat Holding Corp	Methods for the cultivation of DC/D-CIK cells and applications
CN101591280B (zh) *	2008-05-30	2012-08-22	安徽医科大学	具有肿瘤诱导分化作用的类维甲酸衍生物及其药物组合物与用途

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
CH529742A (de) *	1970-02-02	1972-10-31	Hoffmann La Roche	Verfahren zur Herstellung von Vitamin-A-Säureamiden
DE2300107C2 (de) *	1973-01-03	1982-03-11	Basf Ag, 6700 Ludwigshafen	Vitamin A-Säureanilid-4-carbonsäureäthylester, Verfahren zu seiner Herstellung und diesen enthaltende Zubereitungen
US4108880A (en) *	1975-11-03	1978-08-22	Johnson & Johnson	Esters of retinoic acid

1978
- 1978-07-31 US US05/929,093 patent/US4310546A/en not_active Expired - Lifetime
1979
- 1979-05-15 GB GB7916839A patent/GB2026493B/en not_active Expired
- 1979-06-14 CA CA329,779A patent/CA1108170A/en not_active Expired
- 1979-07-25 SE SE7906365A patent/SE442011B/sv not_active IP Right Cessation
- 1979-07-27 IT IT49884/79A patent/IT1162414B/it active
- 1979-07-30 BE BE0/196526A patent/BE877976A/fr not_active IP Right Cessation
- 1979-07-30 AT AT0522979A patent/AT367032B/de not_active IP Right Cessation
- 1979-07-30 NO NO792507A patent/NO149999C/no unknown
- 1979-07-30 FR FR7919566A patent/FR2432509A1/fr active Granted
- 1979-07-30 DE DE19792930923 patent/DE2930923A1/de not_active Ceased
- 1979-07-31 NL NL7905893A patent/NL7905893A/nl not_active Application Discontinuation
- 1979-07-31 DK DK324279A patent/DK324279A/da not_active Application Discontinuation
- 1979-07-31 CH CH705479A patent/CH644845A5/de not_active IP Right Cessation
- 1979-08-08 IE IE1441/79A patent/IE48304B1/en not_active IP Right Cessation

Also Published As

Publication number	Publication date
IE791441L (en)	1980-01-31
SE442011B (sv)	1985-11-25
NO149999B (no)	1984-04-24
GB2026493B (en)	1982-09-29
NO149999C (no)	1984-08-01
IE48304B1 (en)	1984-11-28
US4310546A (en)	1982-01-12
GB2026493A (en)	1980-02-06
FR2432509B1 (de)	1984-03-30
CA1108170A (en)	1981-09-01
DK324279A (da)	1980-02-01
NO792507L (no)	1980-02-01
CH644845A5 (de)	1984-08-31
SE7906365L (sv)	1980-02-01
DE2930923A1 (de)	1980-02-21
BE877976A (fr)	1980-01-30
ATA522979A (de)	1981-10-15
AT367032B (de)	1982-05-25
IT1162414B (it)	1987-04-01
FR2432509A1 (fr)	1980-02-29
IT7949884A0 (it)	1979-07-27

Legal Events

Date	Code	Title	Description
1980-04-25	BT	A notification was added to the application dossier and made available to the public
1984-03-01	BV	The patent application has lapsed

Publication	Publication Date	Title
NL7905893A (nl)	1980-02-04	Werkwijze voor de bereiding van retinoiden en de toepassing daarvan ter voorkoming van carcinogenese.
US4323581A (en)	1982-04-06	Method of treating carcinogenesis
AU667864B2 (en)	1996-04-18	Pharmaceutical compositions
AU2011285724B2 (en)	2015-01-22	Combination therapy for the treatment of prostate carcinoma
JP5785546B2 (ja)	2015-09-30	脳虚血を予防または処置する方法
US5736576A (en)	1998-04-07	Method of treating malignant tumors with thyroxine analogues having no significant hormonal activity
US20090036534A1 (en)	2009-02-05	Method Of Synthesizing S-Allyl-Cysteine Analogues And Their Therapeutic Application In Treating Myocardial Infarction
EP1508561A1 (de)	2005-02-23	BENZOATESÄURE-2-(a-HYDROXYPENTYL)ESTER UND DESSEN HERSTELLUNG UND VERWENDUNG
CA2398923A1 (en)	2001-08-16	A group of anti-cancer compounds with specific structure and their production method
EP2521707A1 (de)	2012-11-14	Bisphenolderivate und ihre verwendung als androgenrezeptoraktivitätsmodulatoren
BRPI0807023A2 (pt)	2014-04-22	Composto de tiazol como ligante de ppard e produto farmacêutico, cosmético e alimento saudável dele composto
US20210283089A1 (en)	2021-09-16	Use of fumaric acid esters and pharmaceutically acceptable salts thereof in preparing pharmaceuticals for treating ferroptosis-related diseases
JPWO2011074643A1 (ja)	2013-04-25	色素沈着予防又は改善剤
JP7362646B2 (ja)	2023-10-17	共結晶
PT100878A (pt)	1993-10-29	Novos retinoides e composicoes farmaceuticas que os contem
BR9814053B1 (pt)	2010-11-30	diésteres lipofìlicos de agentes de quelação.
CN120247669A (zh)	2025-07-04	9,10-二氢菲类化合物及其用于肝损伤治疗的用途
EP0650473B1 (de)	1997-05-28	Phenolische thioether-amine für radiodarstellung und radiochemotherapie und acyl-derivate davon zur verwendung bei diagnose und behandlung von pigmentierungskrankheiten
EP3812365A1 (de)	2021-04-28	Rosmarinsäurederivat oder salz davon
CN111393277B (zh)	2023-01-03	4-丁基多羟基二苯甲酮类化合物衍生物及其应用
JP2782117B2 (ja)	1998-07-30	リン脂質誘導体
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