CS221521B2 - Method of making the derivatives of the 1,4-dioxanaphtalene - Google Patents

Method of making the derivatives of the 1,4-dioxanaphtalene Download PDF

Info

Publication number: CS221521B2
Authority: CS; Czechoslovakia
Prior art keywords: acetone; residue; kpa; evaporated; dissolved
Prior art date: 1978-09-16

Application number

CS796224A

Other languages

Czech (cs)

English (en)

Inventor

Klaus Goerler

Werner Molls

Hildebert Wagner

Won S Woo

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.)

1978-09-16

Filing date

1979-09-14

Publication date

1983-04-29

1979-09-14 Application filed by Madaus & Co Dr filed Critical Madaus & Co Dr

1983-04-29 Publication of CS221521B2 publication Critical patent/CS221521B2/cs

Links

238000004519 manufacturing process Methods 0.000 title description 6
238000000034 method Methods 0.000 claims abstract description 6
150000003839 salts Chemical class 0.000 claims abstract description 6
238000002360 preparation method Methods 0.000 claims abstract description 5
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 52
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 21
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 claims description 21
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 18
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 14
239000003814 drug Substances 0.000 claims description 9
229940079593 drug Drugs 0.000 claims description 9
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 7
239000003208 petroleum Substances 0.000 claims description 6
239000007787 solid Substances 0.000 claims description 6
240000007643 Phytolacca americana Species 0.000 claims description 5
235000009074 Phytolacca americana Nutrition 0.000 claims description 5
239000003480 eluent Substances 0.000 claims description 5
150000004676 glycans Chemical class 0.000 claims description 5
229920001282 polysaccharide Polymers 0.000 claims description 5
239000005017 polysaccharide Substances 0.000 claims description 5
238000003756 stirring Methods 0.000 claims description 5
235000013399 edible fruits Nutrition 0.000 claims description 4
238000009835 boiling Methods 0.000 claims description 3
239000000284 extract Substances 0.000 claims description 3
238000001704 evaporation Methods 0.000 claims 1
230000008020 evaporation Effects 0.000 claims 1
150000001875 compounds Chemical class 0.000 abstract description 10
239000008194 pharmaceutical composition Substances 0.000 abstract 1
OHQVJZXZOCBRIJ-UHFFFAOYSA-N Americanin Chemical compound C1=C(OC)C(OC)=CC=C1CC1C(CC=2C=C(OC)C(OC3C(C(OC(=O)C=CC=4C=C(O)C(O)=CC=4)C(O)C(CO)O3)O)=CC=2)C(=O)OC1 OHQVJZXZOCBRIJ-UHFFFAOYSA-N 0.000 description 6
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 6
241000699670 Mus sp. Species 0.000 description 6
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
239000000047 product Substances 0.000 description 6
239000000243 solution Substances 0.000 description 6
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
210000004185 liver Anatomy 0.000 description 4
BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 4
239000000126 substance Substances 0.000 description 4
239000000829 suppository Substances 0.000 description 4
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
SDDXIQONGFZHJH-UHFFFAOYSA-N Isoamericanin A Natural products OCC1OC2=CC=C(C=CC=O)C=C2OC1C1=CC=C(O)C(O)=C1 SDDXIQONGFZHJH-UHFFFAOYSA-N 0.000 description 3
241001465754 Metazoa Species 0.000 description 3
MBBZMMPHUWSWHV-BDVNFPICSA-N N-methylglucamine Chemical class CNC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO MBBZMMPHUWSWHV-BDVNFPICSA-N 0.000 description 3
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 3
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
239000004480 active ingredient Substances 0.000 description 3
108010003672 americanin Proteins 0.000 description 3
239000000203 mixture Substances 0.000 description 3
230000001681 protective effect Effects 0.000 description 3
OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 2
KPKZJLCSROULON-QKGLWVMZSA-N Phalloidin Chemical compound N1C(=O)[C@@H]([C@@H](O)C)NC(=O)[C@H](C)NC(=O)[C@H](C[C@@](C)(O)CO)NC(=O)[C@H](C2)NC(=O)[C@H](C)NC(=O)[C@@H]3C[C@H](O)CN3C(=O)[C@@H]1CSC1=C2C2=CC=CC=C2N1 KPKZJLCSROULON-QKGLWVMZSA-N 0.000 description 2
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
-1 alkali metal hydrogencarbonates Chemical class 0.000 description 2
230000001929 anti-hepatotoxic effect Effects 0.000 description 2
239000003795 chemical substances by application Substances 0.000 description 2
235000019253 formic acid Nutrition 0.000 description 2
238000002329 infrared spectrum Methods 0.000 description 2
238000001819 mass spectrum Methods 0.000 description 2
230000003389 potentiating effect Effects 0.000 description 2
238000005507 spraying Methods 0.000 description 2
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
238000004809 thin layer chromatography Methods 0.000 description 2
GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 2
238000005303 weighing Methods 0.000 description 2
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
HORQAOAYAYGIBM-UHFFFAOYSA-N 2,4-dinitrophenylhydrazine Chemical compound NNC1=CC=C([N+]([O-])=O)C=C1[N+]([O-])=O HORQAOAYAYGIBM-UHFFFAOYSA-N 0.000 description 1
GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 1
229920000168 Microcrystalline cellulose Polymers 0.000 description 1
108010009711 Phalloidine Proteins 0.000 description 1
239000002202 Polyethylene glycol Substances 0.000 description 1
229920002472 Starch Polymers 0.000 description 1
235000021355 Stearic acid Nutrition 0.000 description 1
HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
238000010521 absorption reaction Methods 0.000 description 1
239000013543 active substance Substances 0.000 description 1
229910052783 alkali metal Inorganic materials 0.000 description 1
229910000288 alkali metal carbonate Inorganic materials 0.000 description 1
150000008041 alkali metal carbonates Chemical class 0.000 description 1
150000001412 amines Chemical class 0.000 description 1
239000003708 ampul Substances 0.000 description 1
238000004458 analytical method Methods 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
239000002775 capsule Substances 0.000 description 1
230000001413 cellular effect Effects 0.000 description 1
239000003153 chemical reaction reagent Substances 0.000 description 1
230000000295 complement effect Effects 0.000 description 1
230000000254 damaging effect Effects 0.000 description 1
238000000354 decomposition reaction Methods 0.000 description 1
238000001514 detection method Methods 0.000 description 1
239000008298 dragée Substances 0.000 description 1
235000011869 dried fruits Nutrition 0.000 description 1
238000000921 elemental analysis Methods 0.000 description 1
238000010828 elution Methods 0.000 description 1
238000002474 experimental method Methods 0.000 description 1
238000000605 extraction Methods 0.000 description 1
230000002349 favourable effect Effects 0.000 description 1
239000012467 final product Substances 0.000 description 1
150000002337 glycosamines Chemical class 0.000 description 1
239000008187 granular material Substances 0.000 description 1
230000002440 hepatic effect Effects 0.000 description 1
238000002347 injection Methods 0.000 description 1
239000007924 injection Substances 0.000 description 1
230000003834 intracellular effect Effects 0.000 description 1
239000008101 lactose Substances 0.000 description 1
239000007788 liquid Substances 0.000 description 1
210000005229 liver cell Anatomy 0.000 description 1
208000019423 liver disease Diseases 0.000 description 1
238000002844 melting Methods 0.000 description 1
230000008018 melting Effects 0.000 description 1
XELZGAJCZANUQH-UHFFFAOYSA-N methyl 1-acetylthieno[3,2-c]pyrazole-5-carboxylate Chemical compound CC(=O)N1N=CC2=C1C=C(C(=O)OC)S2 XELZGAJCZANUQH-UHFFFAOYSA-N 0.000 description 1
235000019813 microcrystalline cellulose Nutrition 0.000 description 1
239000008108 microcrystalline cellulose Substances 0.000 description 1
229940016286 microcrystalline cellulose Drugs 0.000 description 1
IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 1
QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
230000003287 optical effect Effects 0.000 description 1
239000000546 pharmaceutical excipient Substances 0.000 description 1
239000002574 poison Substances 0.000 description 1
231100000614 poison Toxicity 0.000 description 1
229920001223 polyethylene glycol Polymers 0.000 description 1
229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
239000001267 polyvinylpyrrolidone Substances 0.000 description 1
235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
239000012266 salt solution Substances 0.000 description 1
RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 1
239000000377 silicon dioxide Substances 0.000 description 1
235000012239 silicon dioxide Nutrition 0.000 description 1
159000000000 sodium salts Chemical class 0.000 description 1
238000001228 spectrum Methods 0.000 description 1
230000000087 stabilizing effect Effects 0.000 description 1
239000008117 stearic acid Substances 0.000 description 1
239000003826 tablet Substances 0.000 description 1
230000001225 therapeutic effect Effects 0.000 description 1
230000001988 toxicity Effects 0.000 description 1
231100000419 toxicity Toxicity 0.000 description 1
230000002861 ventricular Effects 0.000 description 1
229940100445 wheat starch Drugs 0.000 description 1
239000011701 zinc Substances 0.000 description 1
229910052725 zinc Inorganic materials 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D319/00—Heterocyclic compounds containing six-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D319/10—1,4-Dioxanes; Hydrogenated 1,4-dioxanes
- C07D319/14—1,4-Dioxanes; Hydrogenated 1,4-dioxanes condensed with carbocyclic rings or ring systems
- C07D319/16—1,4-Dioxanes; Hydrogenated 1,4-dioxanes condensed with carbocyclic rings or ring systems condensed with one six-membered ring
- C07D319/20—1,4-Dioxanes; Hydrogenated 1,4-dioxanes condensed with carbocyclic rings or ring systems condensed with one six-membered ring with substituents attached to the hetero ring
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/16—Drugs for disorders of the alimentary tract or the digestive system for liver or gallbladder disorders, e.g. hepatoprotective agents, cholagogues, litholytics

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Pharmacology & Pharmacy (AREA)
Animal Behavior & Ethology (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Engineering & Computer Science (AREA)
Gastroenterology & Hepatology (AREA)
Life Sciences & Earth Sciences (AREA)
Bioinformatics & Cheminformatics (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Medicines Containing Plant Substances (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Steroid Compounds (AREA)
Heterocyclic Compounds That Contain Two Or More Ring Oxygen Atoms (AREA)

CS796224A 1978-09-16 1979-09-14 Method of making the derivatives of the 1,4-dioxanaphtalene CS221521B2 (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
DE19782840467 DE2840467A1 (de)	1978-09-16	1978-09-16	3,4-dihydroxizimtaldehydderivat, dessen herstellung und arzneimittel

Publications (1)

Publication Number	Publication Date
CS221521B2 true CS221521B2 (en)	1983-04-29

Family

ID=6049691

Family Applications (3)

Application Number	Title	Priority Date	Filing Date
CS796224A CS221521B2 (en)	1978-09-16	1979-09-14	Method of making the derivatives of the 1,4-dioxanaphtalene
CS814301A CS221523B2 (en)	1978-09-16	1979-09-14	Method of making the derivative of the 1,4-dioxanaphtalene
CS814300A CS221522B2 (en)	1978-09-16	1979-09-14	Method of making the derivative of the 1,4-dioxanphane

Family Applications After (2)

Application Number	Title	Priority Date	Filing Date
CS814301A CS221523B2 (en)	1978-09-16	1979-09-14	Method of making the derivative of the 1,4-dioxanaphtalene
CS814300A CS221522B2 (en)	1978-09-16	1979-09-14	Method of making the derivative of the 1,4-dioxanphane

Country Status (18)

Country	Link
JP (1)	JPS5559182A (pl)
AR (3)	AR221900A1 (pl)
AT (1)	AT367417B (pl)
BE (1)	BE878824A (pl)
CA (1)	CA1128532A (pl)
CS (3)	CS221521B2 (pl)
DE (1)	DE2840467A1 (pl)
ES (3)	ES8101578A1 (pl)
FR (1)	FR2436145A1 (pl)
GB (1)	GB2035300B (pl)
IT (1)	IT7925651A0 (pl)
LU (1)	LU81679A1 (pl)
NL (1)	NL7906881A (pl)
PL (1)	PL120977B1 (pl)
PT (1)	PT70177A (pl)
SE (1)	SE7907656L (pl)
SU (1)	SU925246A3 (pl)
ZA (1)	ZA794815B (pl)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
FR2851919A1 (fr) *	2003-03-03	2004-09-10	Lmd	Lignanes utilisables comme inhibiteurs de cathepsines et leurs applications

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE2428680C2 (de) *	1974-06-14	1983-02-17	Dr. Madaus & Co, 5000 Köln	1-(2',4',6'-Trihydroxyphenyl)-propandion-(1,2)-Verbindungen, Verfahren zu deren Herstellung und Arzneimittel, die diese Verbindungen enthalten

1978
- 1978-09-16 DE DE19782840467 patent/DE2840467A1/de not_active Withdrawn
1979
- 1979-09-11 ZA ZA00794815A patent/ZA794815B/xx unknown
- 1979-09-12 LU LU81679A patent/LU81679A1/de unknown
- 1979-09-12 IT IT7925651A patent/IT7925651A0/it unknown
- 1979-09-14 PT PT70177A patent/PT70177A/pt unknown
- 1979-09-14 SU SU792811705A patent/SU925246A3/ru active
- 1979-09-14 CS CS796224A patent/CS221521B2/cs unknown
- 1979-09-14 CS CS814301A patent/CS221523B2/cs unknown
- 1979-09-14 NL NL7906881A patent/NL7906881A/nl not_active Application Discontinuation
- 1979-09-14 CS CS814300A patent/CS221522B2/cs unknown
- 1979-09-14 SE SE7907656A patent/SE7907656L/xx not_active Application Discontinuation
- 1979-09-14 FR FR7923013A patent/FR2436145A1/fr active Pending
- 1979-09-14 CA CA335,661A patent/CA1128532A/en not_active Expired
- 1979-09-14 AT AT0607979A patent/AT367417B/de not_active IP Right Cessation
- 1979-09-15 ES ES484202A patent/ES8101578A1/es not_active Expired
- 1979-09-15 PL PL1979218339A patent/PL120977B1/pl unknown
- 1979-09-17 JP JP11800679A patent/JPS5559182A/ja active Pending
- 1979-09-17 AR AR278071A patent/AR221900A1/es active
- 1979-09-17 BE BE0/197176A patent/BE878824A/fr unknown
- 1979-09-17 GB GB7932131A patent/GB2035300B/en not_active Expired
1980
- 1980-01-31 ES ES488140A patent/ES488140A0/es active Granted
- 1980-01-31 ES ES488141A patent/ES488141A0/es active Granted
1981
- 1981-02-25 AR AR284433A patent/AR226094A1/es active
- 1981-02-25 AR AR284432A patent/AR225070A1/es active

Also Published As

Publication number	Publication date
PL218339A1 (pl)	1980-12-01
LU81679A1 (de)	1980-01-24
AR225070A1 (es)	1982-02-15
CA1128532A (en)	1982-07-27
ES8101580A1 (es)	1980-12-16
ES484202A0 (es)	1980-12-16
JPS5559182A (en)	1980-05-02
SE7907656L (sv)	1980-03-17
ES8101579A1 (es)	1980-12-16
CS221522B2 (en)	1983-04-29
DE2840467A1 (de)	1980-03-20
PT70177A (de)	1979-10-01
AR221900A1 (es)	1981-03-31
FR2436145A1 (fr)	1980-04-11
BE878824A (fr)	1980-03-17
AR226094A1 (es)	1982-05-31
ATA607979A (de)	1981-11-15
NL7906881A (nl)	1980-03-18
PL120977B1 (en)	1982-04-30
IT7925651A0 (it)	1979-09-12
AT367417B (de)	1982-07-12
ES8101578A1 (es)	1980-12-16
CS221523B2 (en)	1983-04-29
GB2035300A (en)	1980-06-18
GB2035300B (en)	1983-03-23
ES488141A0 (es)	1980-12-16
SU925246A3 (ru)	1982-04-30
ES488140A0 (es)	1980-12-16
ZA794815B (en)	1980-10-29

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