NO752683L - - Google Patents

Info

Publication number: NO752683L
Authority: NO; Norway
Prior art keywords: vincamine; reaction; starting; mixture; tabersonine
Prior art date: 1974-08-09

Application number

NO752683A

Other languages

English (en)

Norwegian (no)

Inventor

I Taccone

Original Assignee

Buskine Sa

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.)

1974-08-09

Filing date

1975-07-30

Publication date

1976-02-10

1975-07-30 Application filed by Buskine Sa filed Critical Buskine Sa

1976-02-10 Publication of NO752683L publication Critical patent/NO752683L/no

Links

RXPRRQLKFXBCSJ-GIVPXCGWSA-N vincamine Chemical compound C1=CC=C2C(CCN3CCC4)=C5[C@@H]3[C@]4(CC)C[C@](O)(C(=O)OC)N5C2=C1 RXPRRQLKFXBCSJ-GIVPXCGWSA-N 0.000 claims description 47
229960002726 vincamine Drugs 0.000 claims description 30
RXPRRQLKFXBCSJ-UHFFFAOYSA-N dl-Vincamin Natural products C1=CC=C2C(CCN3CCC4)=C5C3C4(CC)CC(O)(C(=O)OC)N5C2=C1 RXPRRQLKFXBCSJ-UHFFFAOYSA-N 0.000 claims description 27
238000006243 chemical reaction Methods 0.000 claims description 23
238000000034 method Methods 0.000 claims description 22
239000000203 mixture Substances 0.000 claims description 18
239000000243 solution Substances 0.000 claims description 17
JSLDLCGKZDUQSH-RTBUJCADSA-N 19-epivindolinine Natural products O=C(OC)[C@H]1[C@@]23[C@H](C)[C@]4([C@@H]5N(CC=C4)CC[C@]25c2c(N3)cccc2)C1 JSLDLCGKZDUQSH-RTBUJCADSA-N 0.000 claims description 12
KILNDJCLJBOWAN-UHFFFAOYSA-N Tabersonine Natural products CCC12CC(=C3N(C)c4cc(OC)ccc4C35CCN(CC=C1)C25)C(=O)OC KILNDJCLJBOWAN-UHFFFAOYSA-N 0.000 claims description 12
FNGGIPWAZSFKCN-ACRUOGEOSA-N tabersonine Chemical compound N1C2=CC=CC=C2[C@]2([C@H]34)C1=C(C(=O)OC)C[C@]3(CC)C=CCN4CC2 FNGGIPWAZSFKCN-ACRUOGEOSA-N 0.000 claims description 12
FNGGIPWAZSFKCN-UHFFFAOYSA-N xi-tabersonine Natural products N1C2=CC=CC=C2C2(C34)C1=C(C(=O)OC)CC3(CC)C=CCN4CC2 FNGGIPWAZSFKCN-UHFFFAOYSA-N 0.000 claims description 12
GIGFIWJRTMBSRP-UHFFFAOYSA-N DL-Vincadifformin Natural products C1C(C(=O)OC)=C2NC3=CC=CC=C3C22CCN3CCCC1(CC)C23 GIGFIWJRTMBSRP-UHFFFAOYSA-N 0.000 claims description 11
GIGFIWJRTMBSRP-ACRUOGEOSA-N (-)-vincadifformine Chemical compound C1C(C(=O)OC)=C2NC3=CC=CC=C3[C@@]22CCN3CCC[C@]1(CC)[C@@H]23 GIGFIWJRTMBSRP-ACRUOGEOSA-N 0.000 claims description 10
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 9
229930013930 alkaloid Natural products 0.000 claims description 9
229910052751 metal Inorganic materials 0.000 claims description 9
239000002184 metal Substances 0.000 claims description 9
150000003839 salts Chemical class 0.000 claims description 9
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 8
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 7
230000002378 acidificating effect Effects 0.000 claims description 6
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 6
238000004519 manufacturing process Methods 0.000 claims description 6
229910052760 oxygen Inorganic materials 0.000 claims description 6
239000001301 oxygen Substances 0.000 claims description 6
-1 hexamethylene phosphor Chemical compound 0.000 claims description 5
239000011541 reaction mixture Substances 0.000 claims description 5
239000007858 starting material Substances 0.000 claims description 5
NAMSIRMSFVGAKD-UHFFFAOYSA-N vincadifformine Natural products CCC12CCCN3CCC4(C13)C(Nc1cc(OC)ccc41)=C(C2)C(=O)OC NAMSIRMSFVGAKD-UHFFFAOYSA-N 0.000 claims description 5
150000003797 alkaloid derivatives Chemical class 0.000 claims description 4
ARUVKPQLZAKDPS-UHFFFAOYSA-L copper(II) sulfate Chemical group [Cu+2].[O-][S+2]([O-])([O-])[O-] ARUVKPQLZAKDPS-UHFFFAOYSA-L 0.000 claims description 4
150000001298 alcohols Chemical class 0.000 claims description 3
229910052802 copper Inorganic materials 0.000 claims description 3
239000010949 copper Substances 0.000 claims description 3
150000007522 mineralic acids Chemical class 0.000 claims description 3
230000008569 process Effects 0.000 claims description 3
239000012429 reaction media Substances 0.000 claims description 3
NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 claims description 2
239000007864 aqueous solution Substances 0.000 claims description 2
229930005303 indole alkaloid Natural products 0.000 claims description 2
150000002475 indoles Chemical class 0.000 claims description 2
XEEYBQQBJWHFJM-UHFFFAOYSA-N iron Substances [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 2
229910052742 iron Inorganic materials 0.000 claims description 2
239000002798 polar solvent Substances 0.000 claims 2
GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical group [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 claims 1
FBAFATDZDUQKNH-UHFFFAOYSA-M iron chloride Chemical compound [Cl-].[Fe] FBAFATDZDUQKNH-UHFFFAOYSA-M 0.000 claims 1
150000002762 monocarboxylic acid derivatives Chemical class 0.000 claims 1
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 39
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 29
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 16
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 12
150000001875 compounds Chemical class 0.000 description 10
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 8
230000002829 reductive effect Effects 0.000 description 8
239000000741 silica gel Substances 0.000 description 8
229910002027 silica gel Inorganic materials 0.000 description 8
238000003786 synthesis reaction Methods 0.000 description 8
RXPRRQLKFXBCSJ-HLAWJBBLSA-N 16-epivincamine Chemical compound C1=CC=C2C(CCN3CCC4)=C5[C@@H]3[C@]4(CC)C[C@@](O)(C(=O)OC)N5C2=C1 RXPRRQLKFXBCSJ-HLAWJBBLSA-N 0.000 description 6
230000015572 biosynthetic process Effects 0.000 description 6
235000019441 ethanol Nutrition 0.000 description 6
238000004809 thin layer chromatography Methods 0.000 description 6
241001246889 Voacanga Species 0.000 description 5
239000002250 absorbent Substances 0.000 description 5
230000002745 absorbent Effects 0.000 description 5
239000003480 eluent Substances 0.000 description 5
230000003647 oxidation Effects 0.000 description 5
238000007254 oxidation reaction Methods 0.000 description 5
238000004587 chromatography analysis Methods 0.000 description 4
230000008018 melting Effects 0.000 description 4
238000002844 melting Methods 0.000 description 4
239000003153 chemical reaction reagent Substances 0.000 description 3
AMFIJXSMYBKJQV-UHFFFAOYSA-L cobalt(2+);octadecanoate Chemical compound [Co+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O AMFIJXSMYBKJQV-UHFFFAOYSA-L 0.000 description 3
239000000284 extract Substances 0.000 description 3
238000002955 isolation Methods 0.000 description 3
239000002904 solvent Substances 0.000 description 3
241000196324 Embryophyta Species 0.000 description 2
SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-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
240000004627 Voacanga thouarsii Species 0.000 description 2
239000003054 catalyst Substances 0.000 description 2
238000004440 column chromatography Methods 0.000 description 2
PXSFGMATQMURKO-UHFFFAOYSA-N dichloromethane;methanol;propan-2-one Chemical compound OC.ClCCl.CC(C)=O PXSFGMATQMURKO-UHFFFAOYSA-N 0.000 description 2
FDSGHYHRLSWSLQ-UHFFFAOYSA-N dichloromethane;propan-2-one Chemical compound ClCCl.CC(C)=O FDSGHYHRLSWSLQ-UHFFFAOYSA-N 0.000 description 2
238000010828 elution Methods 0.000 description 2
238000001704 evaporation Methods 0.000 description 2
230000008020 evaporation Effects 0.000 description 2
239000000499 gel Substances 0.000 description 2
150000003951 lactams Chemical class 0.000 description 2
239000012074 organic phase Substances 0.000 description 2
239000012071 phase Substances 0.000 description 2
230000008707 rearrangement Effects 0.000 description 2
239000000377 silicon dioxide Substances 0.000 description 2
235000012239 silicon dioxide Nutrition 0.000 description 2
229910052938 sodium sulfate Inorganic materials 0.000 description 2
235000011152 sodium sulphate Nutrition 0.000 description 2
238000005507 spraying Methods 0.000 description 2
238000003756 stirring Methods 0.000 description 2
238000006257 total synthesis reaction Methods 0.000 description 2
APJYDQYYACXCRM-UHFFFAOYSA-N tryptamine Chemical compound C1=CC=C2C(CCN)=CNC2=C1 APJYDQYYACXCRM-UHFFFAOYSA-N 0.000 description 2
VDVDQHVHWKOGQF-UHFFFAOYSA-N 4-ethyl-3-formyl-2,2-dimethylheptanedioic acid Chemical compound OC(=O)CCC(CC)C(C=O)C(C)(C)C(O)=O VDVDQHVHWKOGQF-UHFFFAOYSA-N 0.000 description 1
HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 1
VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
241001247482 Amsonia Species 0.000 description 1
241001295727 Amsonia tabernaemontana Species 0.000 description 1
OZDNDGXASTWERN-CTNGQTDRSA-N Apovincamine Chemical compound C1=CC=C2C(CCN3CCC4)=C5[C@@H]3[C@]4(CC)C=C(C(=O)OC)N5C2=C1 OZDNDGXASTWERN-CTNGQTDRSA-N 0.000 description 1
241000238097 Callinectes sapidus Species 0.000 description 1
241000208328 Catharanthus Species 0.000 description 1
241000254273 Crioceras Species 0.000 description 1
208000001953 Hypotension Diseases 0.000 description 1
229910021578 Iron(III) chloride Inorganic materials 0.000 description 1
241000915727 Rhazya stricta Species 0.000 description 1
241001089218 Schizozygia coffaeoides Species 0.000 description 1
241000511964 Tabernaemontana Species 0.000 description 1
241000863480 Vinca Species 0.000 description 1
241000863486 Vinca minor Species 0.000 description 1
235000015799 Voacanga thouarsii Nutrition 0.000 description 1
HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
239000002253 acid Substances 0.000 description 1
238000005903 acid hydrolysis reaction Methods 0.000 description 1
QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Natural products N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 1
OZDNDGXASTWERN-UHFFFAOYSA-N apovincamine Natural products C1=CC=C2C(CCN3CCC4)=C5C3C4(CC)C=C(C(=O)OC)N5C2=C1 OZDNDGXASTWERN-UHFFFAOYSA-N 0.000 description 1
229950006936 apovincamine Drugs 0.000 description 1
PGJHGXFYDZHMAV-UHFFFAOYSA-K azanium;cerium(3+);disulfate Chemical compound [NH4+].[Ce+3].[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O PGJHGXFYDZHMAV-UHFFFAOYSA-K 0.000 description 1
239000002585 base Substances 0.000 description 1
239000008280 blood Substances 0.000 description 1
210000004369 blood Anatomy 0.000 description 1
230000005587 bubbling Effects 0.000 description 1
229910052799 carbon Inorganic materials 0.000 description 1
230000003197 catalytic effect Effects 0.000 description 1
238000009903 catalytic hydrogenation reaction Methods 0.000 description 1
238000010531 catalytic reduction reaction Methods 0.000 description 1
210000003169 central nervous system Anatomy 0.000 description 1
WORJEOGGNQDSOE-UHFFFAOYSA-N chloroform;methanol Chemical compound OC.ClC(Cl)Cl WORJEOGGNQDSOE-UHFFFAOYSA-N 0.000 description 1
229910000365 copper sulfate Inorganic materials 0.000 description 1
239000012043 crude product Substances 0.000 description 1
238000002425 crystallisation Methods 0.000 description 1
230000008025 crystallization Effects 0.000 description 1
230000001419 dependent effect Effects 0.000 description 1
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
208000035475 disorder Diseases 0.000 description 1
230000000694 effects Effects 0.000 description 1
238000006345 epimerization reaction Methods 0.000 description 1
238000000605 extraction Methods 0.000 description 1
230000002349 favourable effect Effects 0.000 description 1
239000012458 free base Substances 0.000 description 1
229910001385 heavy metal Inorganic materials 0.000 description 1
229910052739 hydrogen Inorganic materials 0.000 description 1
239000001257 hydrogen Substances 0.000 description 1
125000004435 hydrogen atom Chemical class [H]* 0.000 description 1
230000007062 hydrolysis Effects 0.000 description 1
238000006460 hydrolysis reaction Methods 0.000 description 1
208000021822 hypotensive Diseases 0.000 description 1
230000001077 hypotensive effect Effects 0.000 description 1
PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 description 1
RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 description 1
239000000543 intermediate Substances 0.000 description 1
RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 description 1
230000007246 mechanism Effects 0.000 description 1
BRMYZIKAHFEUFJ-UHFFFAOYSA-L mercury diacetate Chemical compound CC(=O)O[Hg]OC(C)=O BRMYZIKAHFEUFJ-UHFFFAOYSA-L 0.000 description 1
230000004048 modification Effects 0.000 description 1
238000012986 modification Methods 0.000 description 1
230000007935 neutral effect Effects 0.000 description 1
229910052757 nitrogen Inorganic materials 0.000 description 1
125000004433 nitrogen atom Chemical group N* 0.000 description 1
239000012454 non-polar solvent Substances 0.000 description 1
150000007524 organic acids Chemical class 0.000 description 1
150000001451 organic peroxides Chemical class 0.000 description 1
230000001590 oxidative effect Effects 0.000 description 1
150000004965 peroxy acids Chemical class 0.000 description 1
230000000144 pharmacologic effect Effects 0.000 description 1
CYQAYERJWZKYML-UHFFFAOYSA-N phosphorus pentasulfide Chemical compound S1P(S2)(=S)SP3(=S)SP1(=S)SP2(=S)S3 CYQAYERJWZKYML-UHFFFAOYSA-N 0.000 description 1
238000002360 preparation method Methods 0.000 description 1
239000000047 product Substances 0.000 description 1
238000000746 purification Methods 0.000 description 1
230000009467 reduction Effects 0.000 description 1
238000006722 reduction reaction Methods 0.000 description 1
239000000932 sedative agent Substances 0.000 description 1
230000001624 sedative effect Effects 0.000 description 1
239000011734 sodium Substances 0.000 description 1
239000011877 solvent mixture Substances 0.000 description 1
241000894007 species Species 0.000 description 1
238000001308 synthesis method Methods 0.000 description 1
OKJMLYFJRFYBPS-UHFFFAOYSA-J tetraazanium;cerium(4+);tetrasulfate Chemical compound [NH4+].[NH4+].[NH4+].[NH4+].[Ce+4].[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O OKJMLYFJRFYBPS-UHFFFAOYSA-J 0.000 description 1
150000003571 thiolactams Chemical class 0.000 description 1
239000005418 vegetable material Substances 0.000 description 1
239000002023 wood Substances 0.000 description 1
229910052725 zinc Inorganic materials 0.000 description 1
239000011701 zinc Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D461/00—Heterocyclic compounds containing indolo [3,2,1-d,e] pyrido [3,2,1,j] [1,5]-naphthyridine ring systems, e.g. vincamine

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)
Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)

NO752683A 1974-08-09 1975-07-30 NO752683L (sv)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
CH1094074A CH625239A5 (sv)	1974-08-09	1974-08-09

Publications (1)

Publication Number	Publication Date
NO752683L true NO752683L (sv)	1976-02-10

Family

ID=4368425

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NO752683A NO752683L (sv)	1974-08-09	1975-07-30

Country Status (28)

Country	Link
US (1)	US3979395A (sv)
JP (1)	JPS5141399A (sv)
AR (1)	AR207475A1 (sv)
AT (1)	AT353985B (sv)
BE (1)	BE832157A (sv)
BG (1)	BG24541A3 (sv)
CA (1)	CA1055031A (sv)
CH (1)	CH625239A5 (sv)
CS (1)	CS205003B2 (sv)
DD (1)	DD120441A1 (sv)
DE (1)	DE2534858A1 (sv)
DK (1)	DK141248B (sv)
EG (1)	EG12908A (sv)
ES (1)	ES440120A1 (sv)
FR (1)	FR2281371A1 (sv)
GB (1)	GB1514337A (sv)
IN (1)	IN142318B (sv)
LU (1)	LU73172A1 (sv)
NL (1)	NL7509118A (sv)
NO (1)	NO752683L (sv)
OA (1)	OA05082A (sv)
PL (1)	PL99452B1 (sv)
RO (1)	RO77292A (sv)
SE (1)	SE421315B (sv)
SU (1)	SU612632A3 (sv)
YU (1)	YU201375A (sv)
ZA (1)	ZA754757B (sv)
ZM (1)	ZM11275A1 (sv)

Families Citing this family (8)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
FR2358412A1 (fr) *	1976-07-13	1978-02-10	Parcor	Procede de preparation de la vincamine et d'alcaloides apparentes
DE2745415C2 (de) *	1977-10-08	1983-06-23	Boehringer Mannheim Gmbh, 6800 Mannheim	Verfahren zur Herstellung von (-)-Vincamin
US4285949A (en) *	1978-12-11	1981-08-25	Omnichem Societe Anonyme	Vincamine derivatives, their preparation and therapeutical use
CH646166A5 (it) *	1980-09-30	1984-11-15	Linnea Sa	Procedimento di sintesi parziale della vincamina e di alcaloidi indolici correlati.
CH657617A5 (it) *	1982-10-25	1986-09-15	Istituto Chemioterapico Di Lod	Procedimento per la preparazione di vincamina.
CN102875547B (zh) *	2011-07-15	2015-05-27	海南灵康制药有限公司	一种长春西汀化合物及其制法
CN102911171B (zh) *	2012-10-15	2015-03-04	绍兴民生医药有限公司	一种长春西汀的半合成方法
CN103333166B (zh) *	2013-06-26	2016-07-06	上海交通大学	利用固体酸碱催化合成长春西汀的方法

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US3454583A (en) *	1965-07-19	1969-07-08	Us Health Education & Welfare	Synthesis of vincamine
US3770724A (en) *	1970-03-31	1973-11-06	Roussel Uclaf	Process for preparing pentacyclic alkaloids
FR2179620B1 (sv) *	1972-04-14	1975-12-26	Roussel Uclaf
FR2211004A5 (sv) *	1972-12-15	1974-07-12	Synthelabo

1974
- 1974-08-09 CH CH1094074A patent/CH625239A5/it not_active IP Right Cessation
1975
- 1975-01-01 AR AR259926A patent/AR207475A1/es active
- 1975-07-22 GB GB30701/75A patent/GB1514337A/en not_active Expired
- 1975-07-23 ZA ZA00754757A patent/ZA754757B/xx unknown
- 1975-07-24 AT AT571375A patent/AT353985B/de active
- 1975-07-25 IN IN1466/CAL/75A patent/IN142318B/en unknown
- 1975-07-29 CA CA232,439A patent/CA1055031A/en not_active Expired
- 1975-07-30 NO NO752683A patent/NO752683L/no unknown
- 1975-07-31 NL NL7509118A patent/NL7509118A/xx not_active Application Discontinuation
- 1975-08-01 ZM ZM112/75A patent/ZM11275A1/xx unknown
- 1975-08-02 BG BG7500030715A patent/BG24541A3/xx unknown
- 1975-08-05 JP JP50094806A patent/JPS5141399A/ja active Pending
- 1975-08-05 DE DE19752534858 patent/DE2534858A1/de not_active Withdrawn
- 1975-08-05 YU YU02013/75A patent/YU201375A/xx unknown
- 1975-08-06 RO RO7583094A patent/RO77292A/ro unknown
- 1975-08-06 US US05/602,520 patent/US3979395A/en not_active Expired - Lifetime
- 1975-08-06 BE BE158964A patent/BE832157A/xx not_active IP Right Cessation
- 1975-08-07 FR FR7524708A patent/FR2281371A1/fr active Granted
- 1975-08-07 LU LU73172A patent/LU73172A1/xx unknown
- 1975-08-07 SE SE7508896A patent/SE421315B/sv unknown
- 1975-08-07 DD DD187741A patent/DD120441A1/xx unknown
- 1975-08-08 ES ES440120A patent/ES440120A1/es not_active Expired
- 1975-08-08 SU SU752163172A patent/SU612632A3/ru active
- 1975-08-08 CS CS755512A patent/CS205003B2/cs unknown
- 1975-08-08 PL PL1975182637A patent/PL99452B1/pl unknown
- 1975-08-08 DK DK360475AA patent/DK141248B/da unknown
- 1975-08-09 OA OA55582A patent/OA05082A/xx unknown
- 1975-08-09 EG EG479/75A patent/EG12908A/xx active

Also Published As

Publication number	Publication date
FR2281371A1 (fr)	1976-03-05
AU8385575A (en)	1977-02-17
GB1514337A (en)	1978-06-14
US3979395A (en)	1976-09-07
PL99452B1 (pl)	1978-07-31
FR2281371B1 (sv)	1979-02-02
AT353985B (de)	1979-12-10
YU201375A (en)	1982-06-30
DK360475A (sv)	1976-02-10
BE832157A (fr)	1975-12-01
IN142318B (sv)	1977-06-25
SU612632A3 (ru)	1978-06-25
ZM11275A1 (en)	1976-04-21
AR207475A1 (es)	1976-10-08
CS205003B2 (en)	1981-04-30
SE7508896L (sv)	1976-02-10
EG12908A (en)	1980-07-31
DE2534858A1 (de)	1976-02-19
ES440120A1 (es)	1977-03-01
JPS5141399A (en)	1976-04-07
ZA754757B (en)	1976-07-28
CH625239A5 (sv)	1981-09-15
NL7509118A (nl)	1976-02-11
RO77292A (ro)	1981-08-17
DD120441A1 (sv)	1976-06-12
BG24541A3 (en)	1978-03-10
LU73172A1 (sv)	1976-03-02
SE421315B (sv)	1981-12-14
OA05082A (fr)	1981-01-31
DK141248C (sv)	1980-08-11
ATA571375A (de)	1979-05-15
DK141248B (da)	1980-02-11
CA1055031A (en)	1979-05-22

Publication	Publication Date	Title
PL83152B1 (en)	1975-12-31	Process for preparing pentacyclic alkaloids[us3770724a]
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NO752683L (sv)	1976-02-10
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Wildman et al.	1969	Amaryllidaceae Interconversions. Partial Syntheses of [2] benzopyrano [3, 4-c] indoles
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US3354163A (en)	1967-11-21	Nu-desmethylvinblastine
Nielsen	1970	Bimolecular reduction of isoquinoline. Epimeric 1, 1', 2, 2', 3, 3', 4, 4'-octahydro-1, 1'-biisoquinolines and derivatives
US4045440A (en)	1977-08-30	Method of producing thebaine from codeine and oripavine from morphine
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