LU86556A1 - Methylendioxyphenanthren- und stilbenderivate,verfahren zur herstellung derselben und arzneimittel,die diese enthalten - Google Patents

Methylendioxyphenanthren- und stilbenderivate,verfahren zur herstellung derselben und arzneimittel,die diese enthalten Download PDF

Info

Publication number: LU86556A1
Authority: LU; Luxembourg
Prior art keywords: formula; compound; stilbene; methoxy; converted
Prior art date: 1985-08-28

Application number

LU86556A

Other languages

German (de)

English (en)

Inventor

Klaus Goerler

Guenter Krumbiegel

M Prof Dr Hanack

L Dr Subramanian

Original Assignee

Madaus & Co Dr

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.)

1985-08-28

Filing date

1986-08-20

Publication date

1986-12-02

1986-08-20 Application filed by Madaus & Co Dr filed Critical Madaus & Co Dr

1986-12-02 Publication of LU86556A1 publication Critical patent/LU86556A1/fr

Links

229940079593 drug Drugs 0.000 title 1
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 35
150000001875 compounds Chemical class 0.000 claims description 24
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 22
210000004027 cell Anatomy 0.000 claims description 17
238000002360 preparation method Methods 0.000 claims description 15
SBLSLYIOUALDTC-UHFFFAOYSA-N stilbene;hydrobromide Chemical class Br.C=1C=CC=CC=1C=CC1=CC=CC=C1 SBLSLYIOUALDTC-UHFFFAOYSA-N 0.000 claims description 13
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 12
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 11
206010057249 Phagocytosis Diseases 0.000 claims description 11
239000002253 acid Substances 0.000 claims description 11
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 10
230000008782 phagocytosis Effects 0.000 claims description 10
PJANXHGTPQOBST-UHFFFAOYSA-N stilbene Chemical compound C=1C=CC=CC=1C=CC1=CC=CC=C1 PJANXHGTPQOBST-UHFFFAOYSA-N 0.000 claims description 10
MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 claims description 9
RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 claims description 9
PJANXHGTPQOBST-VAWYXSNFSA-N Stilbene Natural products C=1C=CC=CC=1/C=C/C1=CC=CC=C1 PJANXHGTPQOBST-VAWYXSNFSA-N 0.000 claims description 7
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 7
150000002825 nitriles Chemical class 0.000 claims description 7
239000002904 solvent Substances 0.000 claims description 7
235000021286 stilbenes Nutrition 0.000 claims description 7
XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical compound N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 claims description 6
-1 alkyl carboxylic acid Chemical class 0.000 claims description 6
230000001965 increasing effect Effects 0.000 claims description 6
PKZJLOCLABXVMC-UHFFFAOYSA-N 2-Methoxybenzaldehyde Chemical compound COC1=CC=CC=C1C=O PKZJLOCLABXVMC-UHFFFAOYSA-N 0.000 claims description 5
230000007062 hydrolysis Effects 0.000 claims description 5
238000006460 hydrolysis reaction Methods 0.000 claims description 5
238000000034 method Methods 0.000 claims description 5
229910052757 nitrogen Inorganic materials 0.000 claims description 5
229920001021 polysulfide Polymers 0.000 claims description 5
239000005077 polysulfide Substances 0.000 claims description 5
150000008117 polysulfides Polymers 0.000 claims description 5
230000004913 activation Effects 0.000 claims description 4
229910052740 iodine Inorganic materials 0.000 claims description 4
230000000144 pharmacologic effect Effects 0.000 claims description 4
AOJFQRQNPXYVLM-UHFFFAOYSA-N pyridin-1-ium;chloride Chemical compound [Cl-].C1=CC=[NH+]C=C1 AOJFQRQNPXYVLM-UHFFFAOYSA-N 0.000 claims description 4
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 3
BHUIUXNAPJIDOG-UHFFFAOYSA-N Piperonol Chemical compound OCC1=CC=C2OCOC2=C1 BHUIUXNAPJIDOG-UHFFFAOYSA-N 0.000 claims description 3
241000700159 Rattus Species 0.000 claims description 3
239000007864 aqueous solution Substances 0.000 claims description 3
239000011630 iodine Substances 0.000 claims description 3
230000008569 process Effects 0.000 claims description 3
FJNCXZZQNBKEJT-UHFFFAOYSA-N 8beta-hydroxymarrubiin Natural products O1C(=O)C2(C)CCCC3(C)C2C1CC(C)(O)C3(O)CCC=1C=COC=1 FJNCXZZQNBKEJT-UHFFFAOYSA-N 0.000 claims description 2
QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims description 2
XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 claims description 2
241000283973 Oryctolagus cuniculus Species 0.000 claims description 2
229910052739 hydrogen Inorganic materials 0.000 claims description 2
150000002987 phenanthrenes Chemical class 0.000 claims description 2
125000004435 hydrogen atom Chemical group [H]* 0.000 claims 8
125000002887 hydroxy group Chemical group [H]O* 0.000 claims 8
CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 claims 6
125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims 6
125000003118 aryl group Chemical group 0.000 claims 5
239000003795 chemical substances by application Substances 0.000 claims 5
HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 claims 4
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208000015181 infectious disease Diseases 0.000 claims 4
229910052751 metal Inorganic materials 0.000 claims 4
239000002184 metal Substances 0.000 claims 4
150000004714 phosphonium salts Chemical class 0.000 claims 4
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239000002585 base Substances 0.000 claims 3
150000003839 salts Chemical class 0.000 claims 3
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238000011282 treatment Methods 0.000 claims 3
DUVJMSPTZMCSTQ-UHFFFAOYSA-N 2-ethoxybenzaldehyde Chemical compound CCOC1=CC=CC=C1C=O DUVJMSPTZMCSTQ-UHFFFAOYSA-N 0.000 claims 2
WNMKOPJJPJHXJX-UHFFFAOYSA-N 8-methoxynaphtho[2,1-g][1,3]benzodioxole-5-carboxylic acid Chemical compound C1=CC2=C(C(O)=O)C=C3OCOC3=C2C2=C1C(OC)=CC=C2 WNMKOPJJPJHXJX-UHFFFAOYSA-N 0.000 claims 2
208000035473 Communicable disease Diseases 0.000 claims 2
239000001569 carbon dioxide Substances 0.000 claims 2
229910002092 carbon dioxide Inorganic materials 0.000 claims 2
DOBRDRYODQBAMW-UHFFFAOYSA-N copper(i) cyanide Chemical compound [Cu+].N#[C-] DOBRDRYODQBAMW-UHFFFAOYSA-N 0.000 claims 2
239000003814 drug Substances 0.000 claims 2
150000002828 nitro derivatives Chemical class 0.000 claims 2
QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 claims 2
239000003880 polar aprotic solvent Substances 0.000 claims 2
238000011321 prophylaxis Methods 0.000 claims 2
238000009281 ultraviolet germicidal irradiation Methods 0.000 claims 2
JCEFFRUGDXUMOY-UHFFFAOYSA-N 5-(dibromomethyl)-1,3-benzodioxole Chemical compound BrC(Br)C1=CC=C2OCOC2=C1 JCEFFRUGDXUMOY-UHFFFAOYSA-N 0.000 claims 1
QXKHYNVANLEOEG-UHFFFAOYSA-N Methoxsalen Chemical group C1=CC(=O)OC2=C1C=C1C=COC1=C2OC QXKHYNVANLEOEG-UHFFFAOYSA-N 0.000 claims 1
206010028400 Mutagenic effect Diseases 0.000 claims 1
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 claims 1
208000033809 Suppuration Diseases 0.000 claims 1
208000025865 Ulcer Diseases 0.000 claims 1
150000007513 acids Chemical class 0.000 claims 1
239000013543 active substance Substances 0.000 claims 1
229910052783 alkali metal Inorganic materials 0.000 claims 1
150000001340 alkali metals Chemical class 0.000 claims 1
150000004996 alkyl benzenes Chemical class 0.000 claims 1
125000004429 atom Chemical group 0.000 claims 1
230000031709 bromination Effects 0.000 claims 1
238000005893 bromination reaction Methods 0.000 claims 1
230000001413 cellular effect Effects 0.000 claims 1
238000003776 cleavage reaction Methods 0.000 claims 1
238000009833 condensation Methods 0.000 claims 1
230000005494 condensation Effects 0.000 claims 1
239000003246 corticosteroid Substances 0.000 claims 1
229960001334 corticosteroids Drugs 0.000 claims 1
239000000824 cytostatic agent Substances 0.000 claims 1
230000001085 cytostatic effect Effects 0.000 claims 1
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239000001257 hydrogen Substances 0.000 claims 1
206010020718 hyperplasia Diseases 0.000 claims 1
239000003022 immunostimulating agent Substances 0.000 claims 1
230000003308 immunostimulating effect Effects 0.000 claims 1
238000002513 implantation Methods 0.000 claims 1
230000002401 inhibitory effect Effects 0.000 claims 1
210000000265 leukocyte Anatomy 0.000 claims 1
JILPJDVXYVTZDQ-UHFFFAOYSA-N lithium methoxide Chemical compound [Li+].[O-]C JILPJDVXYVTZDQ-UHFFFAOYSA-N 0.000 claims 1
125000000896 monocarboxylic acid group Chemical group 0.000 claims 1
231100000243 mutagenic effect Toxicity 0.000 claims 1
230000003505 mutagenic effect Effects 0.000 claims 1
CRGUVRKKNCPOBB-UHFFFAOYSA-N naphtho[1,2-g][1,3]benzodioxole Chemical compound C1=CC=C2C3=CC=C4OCOC4=C3C=CC2=C1 CRGUVRKKNCPOBB-UHFFFAOYSA-N 0.000 claims 1
230000005855 radiation Effects 0.000 claims 1
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231100000397 ulcer Toxicity 0.000 claims 1
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210000002540 macrophage Anatomy 0.000 description 36
210000003743 erythrocyte Anatomy 0.000 description 30
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XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 22
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 20
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239000000126 substance Substances 0.000 description 20
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 18
230000000638 stimulation Effects 0.000 description 17
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OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 11
239000002244 precipitate Substances 0.000 description 9
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 8
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YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
239000006144 Dulbecco’s modiﬁed Eagle's medium Substances 0.000 description 6
241000699670 Mus sp. Species 0.000 description 6
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CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 5
238000007912 intraperitoneal administration Methods 0.000 description 5
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238000010992 reflux Methods 0.000 description 5
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FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
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239000008280 blood Substances 0.000 description 4
239000012894 fetal calf serum Substances 0.000 description 4
RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 description 4
JYZNTHFSWOVBAD-UHFFFAOYSA-N phenanthrene;hydrobromide Chemical compound Br.C1=CC=C2C3=CC=CC=C3C=CC2=C1 JYZNTHFSWOVBAD-UHFFFAOYSA-N 0.000 description 4
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HTTJABKRGRZYRN-UHFFFAOYSA-N Heparin Chemical compound OC1C(NC(=O)C)C(O)OC(COS(O)(=O)=O)C1OC1C(OS(O)(=O)=O)C(O)C(OC2C(C(OS(O)(=O)=O)C(OC3C(C(O)C(O)C(O3)C(O)=O)OS(O)(=O)=O)C(CO)O2)NS(O)(=O)=O)C(C(O)=O)O1 HTTJABKRGRZYRN-UHFFFAOYSA-N 0.000 description 2
229910021578 Iron(III) chloride Inorganic materials 0.000 description 2
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239000000084 colloidal system Substances 0.000 description 2
LEKPFOXEZRZPGW-UHFFFAOYSA-N copper;dicyanide Chemical compound [Cu+2].N#[C-].N#[C-] LEKPFOXEZRZPGW-UHFFFAOYSA-N 0.000 description 2
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HZFNJOLNDQWEDY-UHFFFAOYSA-N phenanthrene-1-carbonitrile Chemical compound C1=CC2=CC=CC=C2C2=C1C(C#N)=CC=C2 HZFNJOLNDQWEDY-UHFFFAOYSA-N 0.000 description 2
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239000000725 suspension Substances 0.000 description 1
239000008399 tap water Substances 0.000 description 1
235000020679 tap water Nutrition 0.000 description 1
229940071127 thioglycolate Drugs 0.000 description 1
CWERGRDVMFNCDR-UHFFFAOYSA-M thioglycolate(1-) Chemical compound [O-]C(=O)CS CWERGRDVMFNCDR-UHFFFAOYSA-M 0.000 description 1
LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
238000010792 warming Methods 0.000 description 1
230000003313 weakening effect Effects 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
- C07D317/44—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D317/70—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems condensed with ring systems containing two or more relevant rings
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/12—Antivirals
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/02—Immunomodulators
- A61P37/04—Immunostimulants
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
- C07D317/44—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D317/46—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems condensed with one six-membered ring
- C07D317/48—Methylenedioxybenzenes or hydrogenated methylenedioxybenzenes, unsubstituted on the hetero ring
- C07D317/62—Methylenedioxybenzenes or hydrogenated methylenedioxybenzenes, unsubstituted on the hetero ring with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to atoms of the carbocyclic ring
- C07D317/68—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
Pharmacology & Pharmacy (AREA)
Public Health (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Chemical Kinetics & Catalysis (AREA)
Veterinary Medicine (AREA)
Immunology (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Communicable Diseases (AREA)
Oncology (AREA)
Engineering & Computer Science (AREA)
Virology (AREA)
Bioinformatics & Cheminformatics (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

LU86556A 1985-08-28 1986-08-20 Methylendioxyphenanthren- und stilbenderivate,verfahren zur herstellung derselben und arzneimittel,die diese enthalten LU86556A1 (fr)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
DE3530718		1985-08-28
DE19853530718 DE3530718A1 (de)	1985-08-28	1985-08-28	Methylendioxyphenanthren- und -stilbenderivate, verfahren zur herstellung derselben und arzneimittel, die diese enthalten

Publications (1)

Publication Number	Publication Date
LU86556A1 true LU86556A1 (fr)	1986-12-02

Family

ID=6279566

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
LU86556A LU86556A1 (fr)	1985-08-28	1986-08-20	Methylendioxyphenanthren- und stilbenderivate,verfahren zur herstellung derselben und arzneimittel,die diese enthalten

Country Status (27)

Country	Link
US (2)	US4835178A (fr)
JP (1)	JPS62167776A (fr)
KR (1)	KR880000179B1 (fr)
AR (1)	AR242568A1 (fr)
AT (1)	AT398568B (fr)
BE (1)	BE905340A (fr)
CH (1)	CH673457A5 (fr)
DD (1)	DD266800A5 (fr)
DE (1)	DE3530718A1 (fr)
DK (1)	DK168705B1 (fr)
ES (1)	ES2001893A6 (fr)
FI (1)	FI92396C (fr)
FR (1)	FR2586681B1 (fr)
GB (1)	GB2179347B (fr)
HU (3)	HU895304D0 (fr)
IE (1)	IE59239B1 (fr)
IT (1)	IT1197467B (fr)
LU (1)	LU86556A1 (fr)
MX (2)	MX172917B (fr)
NL (1)	NL8602127A (fr)
NO (1)	NO863434L (fr)
PL (2)	PL148757B1 (fr)
PT (1)	PT83258B (fr)
SE (1)	SE465153B (fr)
SU (1)	SU1731053A3 (fr)
YU (2)	YU44061B (fr)
ZA (1)	ZA866487B (fr)

Families Citing this family (6)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
ES2038573T1 (es) *	1989-12-15	1993-08-01	Pharma Mar, S.A.	Nuevos compuestos del tipo diterpeno.
EP0498095B1 (fr) *	1991-02-05	1995-01-04	Merrell Dow Pharmaceuticals Inc.	Dérivés de stilbène sulfonique pour le traitement de maladies virales
JP3309104B2 (ja) *	1992-02-20	2002-07-29	メレルダウファーマス−ティカルズインコーポレイテッド	ウイルス病治療用のスルホン酸誘導体類
US5334615A (en) *	1992-12-17	1994-08-02	Walles Wilhelm E	Oil with bactericidal and virucidal properties
US5739166A (en) *	1994-11-29	1998-04-14	G.D. Searle & Co.	Substituted terphenyl compounds for the treatment of inflammation
CN112778264B (zh) *	2021-01-21	2023-09-15	江西农业大学	马兜铃次酸衍生物及其在制备抗炎药物中的应用

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4122092A (en) *	1977-08-25	1978-10-24	University Of Rochester	Total synthesis of (±)-picropodophyllone and (±)-4'-demethylpicropodophyllone
JPS57106677A (en) *	1980-12-22	1982-07-02	Kureha Chem Ind Co Ltd	N-(3,4-methylenedioxybenzylidene) aminomethylcyclohexane-carboxylic acid, and salt of said carboxylic acid

1985
- 1985-08-28 DE DE19853530718 patent/DE3530718A1/de active Granted
1986
- 1986-08-08 AT AT0215186A patent/AT398568B/de not_active IP Right Cessation
- 1986-08-12 GB GB8619644A patent/GB2179347B/en not_active Expired
- 1986-08-13 FI FI863282A patent/FI92396C/fi not_active IP Right Cessation
- 1986-08-20 AR AR86304988A patent/AR242568A1/es active
- 1986-08-20 LU LU86556A patent/LU86556A1/fr unknown
- 1986-08-21 NL NL8602127A patent/NL8602127A/nl not_active Application Discontinuation
- 1986-08-22 YU YU1475/86A patent/YU44061B/xx unknown
- 1986-08-25 CH CH3406/86A patent/CH673457A5/de not_active IP Right Cessation
- 1986-08-26 IT IT8621526A patent/IT1197467B/it active
- 1986-08-26 SE SE8603589A patent/SE465153B/sv not_active IP Right Cessation
- 1986-08-26 MX MX003550A patent/MX172917B/es unknown
- 1986-08-27 ES ES8601409A patent/ES2001893A6/es not_active Expired
- 1986-08-27 DK DK407586A patent/DK168705B1/da not_active IP Right Cessation
- 1986-08-27 SU SU864028078A patent/SU1731053A3/ru active
- 1986-08-27 PL PL1986261196A patent/PL148757B1/pl unknown
- 1986-08-27 DD DD86293892A patent/DD266800A5/de not_active IP Right Cessation
- 1986-08-27 NO NO863434A patent/NO863434L/no unknown
- 1986-08-27 PT PT83258A patent/PT83258B/pt not_active IP Right Cessation
- 1986-08-27 IE IE228886A patent/IE59239B1/en not_active IP Right Cessation
- 1986-08-27 HU HU895304A patent/HU895304D0/hu not_active IP Right Cessation
- 1986-08-27 HU HU895304A patent/HU202104B/hu not_active IP Right Cessation
- 1986-08-27 ZA ZA866487A patent/ZA866487B/xx unknown
- 1986-08-27 HU HU863711A patent/HU199446B/hu not_active IP Right Cessation
- 1986-08-27 BE BE0/217092A patent/BE905340A/fr not_active IP Right Cessation
- 1986-08-27 FR FR868612129A patent/FR2586681B1/fr not_active Expired - Lifetime
- 1986-08-27 PL PL1986268178A patent/PL154026B1/pl unknown
- 1986-08-28 KR KR1019860007146A patent/KR880000179B1/ko not_active Expired
- 1986-08-28 JP JP61200261A patent/JPS62167776A/ja active Granted
1987
- 1987-06-19 YU YU1149/87A patent/YU43998B/xx unknown
1988
- 1988-03-22 US US07/171,695 patent/US4835178A/en not_active Expired - Fee Related
1989
- 1989-12-27 US US07/457,353 patent/US5024743A/en not_active Expired - Fee Related
1993
- 1993-01-27 MX MX9300436A patent/MX9300436A/es unknown

Also Published As

Publication number	Publication date
HU202104B (en)	1991-02-28
PT83258B (pt)	1988-07-01
SE8603589L (sv)	1987-03-01
PL148757B1 (en)	1989-11-30
FI92396C (fi)	1994-11-10
KR870002119A (ko)	1987-03-30
ATA215186A (de)	1994-05-15
FI92396B (fi)	1994-07-29
DD266800A5 (de)	1989-04-12
MX9300436A (es)	1994-07-29
PL268178A1 (en)	1988-10-13
YU147586A (en)	1988-02-29
YU43998B (en)	1990-02-28
FI863282L (fi)	1987-03-01
DE3530718A1 (de)	1987-03-12
IE59239B1 (en)	1994-01-26
FR2586681A1 (fr)	1987-03-06
US4835178A (en)	1989-05-30
CH673457A5 (fr)	1990-03-15
DE3530718C2 (fr)	1992-07-09
JPS62167776A (ja)	1987-07-24
YU114987A (en)	1988-02-29
NO863434L (no)	1987-03-02
MX3550A (es)	1993-10-01
HUT44775A (en)	1988-04-28
PL261196A1 (en)	1988-02-04
DK407586D0 (da)	1986-08-27
GB2179347B (en)	1989-08-09
AT398568B (de)	1994-12-27
NO863434D0 (no)	1986-08-27
PL154026B1 (en)	1991-06-28
GB2179347A (en)	1987-03-04
SE465153B (sv)	1991-08-05
FR2586681B1 (fr)	1991-02-22
YU44061B (en)	1990-02-28
SE8603589D0 (sv)	1986-08-26
MX172917B (es)	1994-01-21
US5024743A (en)	1991-06-18
IT8621526A0 (it)	1986-08-26
SU1731053A3 (ru)	1992-04-30
PT83258A (de)	1986-09-01
DK407586A (da)	1987-03-01
IT1197467B (it)	1988-11-30
FI863282A0 (fi)	1986-08-13
JPH0349908B2 (fr)	1991-07-31
ES2001893A6 (es)	1988-07-01
KR880000179B1 (ko)	1988-03-12
AR242568A1 (es)	1993-04-30
DK168705B1 (da)	1994-05-24
ZA866487B (en)	1987-04-29
HU895304D0 (en)	1990-03-28
GB8619644D0 (en)	1986-09-24
IE862288L (en)	1987-02-28
BE905340A (fr)	1987-02-27
HU199446B (en)	1990-02-28
NL8602127A (nl)	1987-03-16

Legal Events

Date	Code	Title	Description
1986-08-20	DT	Application date
1991-06-19	TA	Annual fee

Publication	Publication Date	Title
CH648037A5 (de)	1985-02-28	Imidazo-rifamycin-derivate mit antibakterieller wirksamkeit.
EP0084667A2 (fr)	1983-08-03	Dérivés de phényléthylène, leur préparation et utilisation à titre de médicaments
AT398568B (de)	1994-12-27	Verfahren zur herstellung von methylendioxyphenanthren- und -stilbenderivaten
DD210687A5 (de)	1984-06-20	Verfahren zur herstellung von (+)-cyanidan-3-ol-derivaten
DE4440141A1 (de)	1996-05-15	Neue kristalline Cephem-Säureadditionssalze und Verfahren zu ihrer Herstellung
DE2323746A1 (de)	1973-11-29	Mono- und diester der 2,5-dihydroxybenzolsulfonsaeure
EP0004522B1 (fr)	1982-06-23	Nouveaux composés analogues aux dilignols, composés analogues aux dilignols utilisable dans le traitement des maledies hépatiques et compositions pharmaceutiques les contenant
DE2605377A1 (de)	1976-08-26	0-aminooxime, verfahren zu ihrer herstellung und sie enthaltende arzneimittel
EP0065692B1 (fr)	1984-12-19	Erythro-1,2,3-triphényl-1-pentanones, procédé pour leur préparation et leur utilisation comme médicament
DE2463023C2 (de)	1984-10-11	S-Triazolo-[5,1-a]-isochinolinderivate, deren Salze und Verfahren zu deren Herstellung
DE1468279C3 (fr)	1973-09-27
DE2603596C2 (de)	1984-03-01	Glycyrrhetinsäurederivate, Verfahren zu ihrer Herstellung und sie enthaltende Arzneimittel
DE2530289A1 (de)	1976-01-29	Neue benzopyranderivate verfahren zu deren herstellung und diese enthaltende pharmazeutische zusammensetzungen
DE69910810T2 (de)	2004-08-19	Natriumsalz von 3-(4-cinnamyl-1-piperazinyl)-iminomethyl-rifamycin sv und verfahren zu seiner herstellung
DE2646213A1 (de)	1977-05-12	Aroylphenylnaphthaline und verfahren zu ihrer herstellung
DE3104785A1 (de)	1982-02-25	Basische ether der 4-hydroxy-benzophenone, die als (beta)-blocker wirksam sind, und verfahren zu ihrer herstellung
DE2530768C3 (de)	1979-07-26	PhenoxyaUcylaminpyridyläther, Verfahren zu ihrer Herstellung sowie diese enthaltende pharmazeutische Präparate
DE2537204A1 (de)	1976-03-04	Neue benzopyrane und verfahren zu ihrer herstellung
DE825264C (de)	1951-12-17	Verfahren zur Herstellung von diquartaeren Salzen von Pyrimidylaminochinolinen
DE3414051A1 (de)	1984-10-18	Hydroxylgruppenhaltige diphenylazomethine, verfahren zu ihrer herstellung und ihre anwendung in der therapie
DE69612626T2 (de)	2001-09-13	Hydrat-kristall und verfahren zu seiner herstellung
DE2542096A1 (de)	1976-04-08	Symmetrische hydroxythioalkane, verfahren zu ihrer herstellung und diese enthaltende heilmittel
DE2535348A1 (de)	1976-02-19	Verfahren zur herstellung und verwendung von stabilisierten gefaessaktiven verbindungen
DE875527C (de)	1953-05-04	Verfahren zur Herstellung basischer Formaldehydderivate
AT260216B (de)	1968-02-12	Verfahren zur Herstellung des neuen 2-Benzylphenyl-β-dimethylaminoäthyläther-pamoats und -aluminiumpamoats