NO119416B - - Google Patents

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Info

Publication number: NO119416B
Authority: NO; Norway
Prior art keywords: demethyl; epipodophyllotoxin; podophyllotoxin; chloroform; compound
Prior art date: 1964-08-12

Application number

NO165461A

Other languages

English (en)

Norwegian (no)

Inventor

Wartburg A Von

M Kuhn

J Renz

Original Assignee

Sandoz Ag

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.)

1964-08-12

Filing date

1966-11-04

Publication date

1970-05-19

1966-11-04 Application filed by Sandoz Ag filed Critical Sandoz Ag

1970-05-19 Publication of NO119416B publication Critical patent/NO119416B/no

Links

HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 8
238000000034 method Methods 0.000 claims description 8
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 6
238000004519 manufacturing process Methods 0.000 claims description 4
229960001237 podophyllotoxin Drugs 0.000 claims description 4
YJGVMLPVUAXIQN-UHFFFAOYSA-N epipodophyllotoxin Natural products COC1=C(OC)C(OC)=CC(C2C3=CC=4OCOC=4C=C3C(O)C3C2C(OC3)=O)=C1 YJGVMLPVUAXIQN-UHFFFAOYSA-N 0.000 claims description 3
238000002425 crystallisation Methods 0.000 claims description 2
230000008025 crystallization Effects 0.000 claims description 2
YVCVYCSAAZQOJI-UHFFFAOYSA-N podophyllotoxin Natural products COC1=C(O)C(OC)=CC(C2C3=CC=4OCOC=4C=C3C(O)C3C2C(OC3)=O)=C1 YVCVYCSAAZQOJI-UHFFFAOYSA-N 0.000 claims description 2
239000003480 eluent Substances 0.000 claims 1
239000012535 impurity Substances 0.000 claims 1
238000002844 melting Methods 0.000 claims 1
230000008018 melting Effects 0.000 claims 1
239000007858 starting material Substances 0.000 claims 1
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 8
150000001875 compounds Chemical class 0.000 description 7
239000002253 acid Substances 0.000 description 4
150000007513 acids Chemical class 0.000 description 3
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 2
210000003855 cell nucleus Anatomy 0.000 description 2
239000007795 chemical reaction product Substances 0.000 description 2
238000006345 epimerization reaction Methods 0.000 description 2
230000002401 inhibitory effect Effects 0.000 description 2
239000000203 mixture Substances 0.000 description 2
239000007787 solid Substances 0.000 description 2
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
FOVRGQUEGRCWPD-UHFFFAOYSA-N (5aR)-9t-beta-D-Glucopyranosyloxy-5t-(4-hydroxy-3,5-dimethoxy-phenyl)-(5ar,8at)-5,8,8a,9-tetrahydro-5aH-furo[3',4';6,7]naphtho[2,3-d][1,3]dioxol-6-on Natural products COC1=C(O)C(OC)=CC(C2C3=CC=4OCOC=4C=C3C(OC3C(C(O)C(O)C(CO)O3)O)C3C2C(OC3)=O)=C1 FOVRGQUEGRCWPD-UHFFFAOYSA-N 0.000 description 1
NXVJTGLCCSFGAT-QNDDJFOYSA-N (5r,5ar,8ar,9r)-5-[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-9-(3,4,5-trimethoxyphenyl)-5a,6,8a,9-tetrahydro-5h-[2]benzofuro[6,5-f][1,3]benzodioxol-8-one Chemical compound COC1=C(OC)C(OC)=CC([C@@H]2C3=CC=4OCOC=4C=C3[C@H](O[C@H]3[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O3)O)[C@@H]3[C@@H]2C(OC3)=O)=C1 NXVJTGLCCSFGAT-QNDDJFOYSA-N 0.000 description 1
YVCVYCSAAZQOJI-JHQYFNNDSA-N 4'-demethylepipodophyllotoxin Chemical compound COC1=C(O)C(OC)=CC([C@@H]2C3=CC=4OCOC=4C=C3[C@@H](O)[C@@H]3[C@@H]2C(OC3)=O)=C1 YVCVYCSAAZQOJI-JHQYFNNDSA-N 0.000 description 1
206010012735 Diarrhoea Diseases 0.000 description 1
241000699670 Mus sp. Species 0.000 description 1
206010028813 Nausea Diseases 0.000 description 1
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
206010047700 Vomiting Diseases 0.000 description 1
229940045696 antineoplastic drug podophyllotoxin derivative Drugs 0.000 description 1
AYJRCSIUFZENHW-DEQYMQKBSA-L barium(2+);oxomethanediolate Chemical compound [Ba+2].[O-][14C]([O-])=O AYJRCSIUFZENHW-DEQYMQKBSA-L 0.000 description 1
230000032823 cell division Effects 0.000 description 1
230000010261 cell growth Effects 0.000 description 1
230000004663 cell proliferation Effects 0.000 description 1
238000006243 chemical reaction Methods 0.000 description 1
238000004587 chromatography analysis Methods 0.000 description 1
238000003776 cleavage reaction Methods 0.000 description 1
231100000433 cytotoxic Toxicity 0.000 description 1
230000001472 cytotoxic effect Effects 0.000 description 1
239000003814 drug Substances 0.000 description 1
238000001035 drying Methods 0.000 description 1
230000000694 effects Effects 0.000 description 1
239000000706 filtrate Substances 0.000 description 1
210000003630 histaminocyte Anatomy 0.000 description 1
238000000338 in vitro Methods 0.000 description 1
229910052500 inorganic mineral Inorganic materials 0.000 description 1
201000006512 mast cell neoplasm Diseases 0.000 description 1
239000011707 mineral Substances 0.000 description 1
230000008693 nausea Effects 0.000 description 1
239000003960 organic solvent Substances 0.000 description 1
238000007911 parenteral administration Methods 0.000 description 1
239000000546 pharmaceutical excipient Substances 0.000 description 1
YJGVMLPVUAXIQN-XVVDYKMHSA-N podophyllotoxin Chemical class COC1=C(OC)C(OC)=CC([C@@H]2C3=CC=4OCOC=4C=C3[C@H](O)[C@@H]3[C@@H]2C(OC3)=O)=C1 YJGVMLPVUAXIQN-XVVDYKMHSA-N 0.000 description 1
239000003600 podophyllotoxin derivative Substances 0.000 description 1
238000010992 reflux Methods 0.000 description 1
230000007017 scission Effects 0.000 description 1
239000000741 silica gel Substances 0.000 description 1
229910002027 silica gel Inorganic materials 0.000 description 1
229910052938 sodium sulfate Inorganic materials 0.000 description 1
235000011152 sodium sulphate Nutrition 0.000 description 1
230000001225 therapeutic effect Effects 0.000 description 1
230000008673 vomiting Effects 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D493/00—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system
- C07D493/02—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system in which the condensed system contains two hetero rings
- C07D493/04—Ortho-condensed systems

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Saccharide Compounds (AREA)
Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)

NO165461A 1964-08-12 1966-11-04 NO119416B (es)

Applications Claiming Priority (3)

Application Number	Priority Date	Filing Date	Title
CH1050964A CH454169A (de)	1964-08-12	1964-08-12	Verfahren zur Herstellung von neuen Podophyllotoxin-Derivaten
CH788865		1965-06-04
CH819965		1965-06-11

Publications (1)

Publication Number	Publication Date
NO119416B true NO119416B (es)	1970-05-19

Family

ID=27175878

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NO165461A NO119416B (es)	1964-08-12	1966-11-04

Country Status (14)

Country	Link
AT (1)	AT268540B (es)
BE (1)	BE668122A (es)
BR (1)	BR6572038D0 (es)
CH (1)	CH454169A (es)
DE (1)	DE1518324A1 (es)
DK (3)	DK113368B (es)
ES (3)	ES316314A1 (es)
FI (1)	FI44410B (es)
FR (2)	FR1468767A (es)
GB (1)	GB1114123A (es)
IL (1)	IL24135A (es)
NL (1)	NL6510414A (es)
NO (1)	NO119416B (es)
OA (1)	OA01792A (es)

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US6894075B2 (en) *	2000-11-20	2005-05-17	Song-Bae Kim	4′-demethyl-4′-O-substituted-1-deoxypodophyllotoxin derivative and geometric isomer thereof, process for the preparation thereof and anti-cancer composition comprising the same
US7342114B2 (en) *	2003-07-01	2008-03-11	California Pacific Medical Center	Podophyllotoxin derivatives
US10087194B2 (en)	2015-10-27	2018-10-02	California Pacific Medical Center	Podophyllotoxin derivatives and their use
EP3371192B1 (en)	2015-10-27	2020-06-03	California Pacific Medical Center	Podophyllotoxin derivatives and their use

1964
- 1964-08-12 CH CH1050964A patent/CH454169A/de unknown
1965
- 1965-07-30 GB GB32730/65A patent/GB1114123A/en not_active Expired
- 1965-08-06 DE DE19651518324 patent/DE1518324A1/de active Pending
- 1965-08-10 FR FR27816A patent/FR1468767A/fr not_active Expired
- 1965-08-10 NL NL6510414A patent/NL6510414A/xx unknown
- 1965-08-10 ES ES0316314A patent/ES316314A1/es not_active Expired
- 1965-08-10 BE BE668122D patent/BE668122A/xx unknown
- 1965-08-11 FI FI1939/65A patent/FI44410B/fi active
- 1965-08-11 OA OA52144A patent/OA01792A/xx unknown
- 1965-08-11 IL IL24135A patent/IL24135A/xx unknown
- 1965-08-11 BR BR172038/65A patent/BR6572038D0/pt unknown
- 1965-08-11 AT AT823567A patent/AT268540B/de active
- 1965-10-14 ES ES0318461A patent/ES318461A1/es not_active Expired
- 1965-10-14 ES ES0318460A patent/ES318460A1/es not_active Expired
- 1965-11-09 FR FR37802A patent/FR4867M/fr not_active Expired
1966
- 1966-09-21 DK DK490566AA patent/DK113368B/da unknown
- 1966-09-21 DK DK490666AA patent/DK111362B/da unknown
- 1966-11-04 NO NO165461A patent/NO119416B/no unknown
1968
- 1968-03-14 DK DK108468AA patent/DK116294B/da unknown

Also Published As

Publication number	Publication date
BE668122A (es)	1966-02-10
BR6572038D0 (pt)	1973-08-16
IL24135A (en)	1969-02-27
FR4867M (es)	1967-02-27
AT268540B (de)	1969-02-10
FR1468767A (fr)	1967-02-10
GB1114123A (en)	1968-05-15
ES318460A1 (es)	1966-04-01
ES316314A1 (es)	1966-04-16
DE1518324A1 (de)	1969-08-21
OA01792A (fr)	1970-01-14
DK113368B (da)	1969-03-17
DK111362B (da)	1968-08-05
NL6510414A (es)	1966-02-14
ES318461A1 (es)	1966-06-01
CH454169A (de)	1968-04-15
DK116294B (da)	1969-12-29
FI44410B (es)	1971-08-02

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US2265207A (en)	1941-12-09	D-lysergic acid - d - l-bjtdroxybutyl
US2390395A (en)	1945-12-04	Sorbitan and process for making the same
US3397231A (en)	1968-08-13	Refining of alpha-6-deoxy-5-oxytetracycline
NO126320B (es)	1973-01-22
US3426017A (en)	1969-02-04	Sulfonylurea compounds
US3583992A (en)	1971-06-08	1-methyl-d-lysergic acid-dihydroxy-alkyl-amides
NO127920B (es)	1973-09-03
US2912436A (en)	1959-11-10	Brominated alkaloids
NO118975B (es)	1970-03-09
Deulofeu et al.	1947	Studies on argentine plants. VIII. The alkaloids of Erythrina crista galli. Chromatographic separation of erythratine and erysodine
US2802006A (en)	1957-08-06	Esters of the yohimbe alkaloids
US2040145A (en)	1936-05-12	Beta-methylcholine derivatives and salts and processes for their production
NO118262B (es)	1969-12-01
Frush et al.	1948	Amides of glucuronic, galacturonic, and mannuronic acids
US3551432A (en)	1970-12-29	1-loweralkanoyl-nipecotonitriles
EP0180833A1 (de)	1986-05-14	4-Oxo-pyrido[2,3]pyrimidin-Derivate, Verfahren zur deren Herstellung und diese ethaltende Arzneimittel
US3120528A (en)	1964-02-04	Derivatives of 17-ketoyohimbane alkaloids and process therefor