LU81145A1 - Derives de la tetrahydroalstonine et leur application en therapeutique - Google Patents

Derives de la tetrahydroalstonine et leur application en therapeutique Download PDF

Info

Publication number: LU81145A1
Authority: LU; Luxembourg
Prior art keywords: radical; acid; compounds; alkoxy; alkyl
Prior art date: 1978-04-14

Application number

LU81145A

Other languages

English (en)

French (fr)

Inventor

H Najer

B Mompon

B Shroot

Original Assignee

Synthelabo

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.)

1978-04-14

Filing date

1979-04-12

Publication date

1980-12-16

1978-04-14 Priority claimed from FR7811026A external-priority patent/FR2422664A1/fr

1979-04-12 Application filed by Synthelabo filed Critical Synthelabo

1980-12-16 Publication of LU81145A1 publication Critical patent/LU81145A1/fr

Links

ZLQMRLSBXKQKMG-UHFFFAOYSA-N rauniticine Natural products COC(=O)C1=CC2CC3N(CCc4c3[nH]c5ccccc45)CC2C(C)O1 ZLQMRLSBXKQKMG-UHFFFAOYSA-N 0.000 title claims description 11
230000001225 therapeutic effect Effects 0.000 title description 2
150000001875 compounds Chemical class 0.000 claims description 25
239000002253 acid Substances 0.000 claims description 23
-1 piperidino, morpholino Chemical group 0.000 claims description 18
GRTOGORTSDXSFK-DLLGKBFGSA-N tetrahydroalstonine Chemical compound C1=CC=C2C(CCN3C[C@H]4[C@H](C)OC=C([C@H]4C[C@H]33)C(=O)OC)=C3NC2=C1 GRTOGORTSDXSFK-DLLGKBFGSA-N 0.000 claims description 13
125000004432 carbon atom Chemical group C* 0.000 claims description 6
125000000217 alkyl group Chemical group 0.000 claims description 5
238000006243 chemical reaction Methods 0.000 claims description 5
229910052784 alkaline earth metal Inorganic materials 0.000 claims description 4
150000003839 salts Chemical class 0.000 claims description 4
150000007513 acids Chemical class 0.000 claims description 3
239000003513 alkali Substances 0.000 claims description 2
150000001342 alkaline earth metals Chemical class 0.000 claims description 2
150000001408 amides Chemical class 0.000 claims description 2
MDFFNEOEWAXZRQ-UHFFFAOYSA-N aminyl Chemical compound [NH2] MDFFNEOEWAXZRQ-UHFFFAOYSA-N 0.000 claims description 2
238000007796 conventional method Methods 0.000 claims description 2
125000000753 cycloalkyl group Chemical group 0.000 claims description 2
230000032050 esterification Effects 0.000 claims description 2
238000005886 esterification reaction Methods 0.000 claims description 2
230000022244 formylation Effects 0.000 claims description 2
238000006170 formylation reaction Methods 0.000 claims description 2
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
125000002768 hydroxyalkyl group Chemical group 0.000 claims description 2
TUJKJAMUKRIRHC-UHFFFAOYSA-N hydroxyl Chemical compound [OH] TUJKJAMUKRIRHC-UHFFFAOYSA-N 0.000 claims description 2
150000004702 methyl esters Chemical class 0.000 claims description 2
238000002360 preparation method Methods 0.000 claims description 2
125000002112 pyrrolidino group Chemical group [*]N1C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 2
125000001424 substituent group Chemical group 0.000 claims description 2
238000005809 transesterification reaction Methods 0.000 claims description 2
238000000034 method Methods 0.000 claims 2
125000005843 halogen group Chemical group 0.000 claims 1
229940126601 medicinal product Drugs 0.000 claims 1
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 38
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 21
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 21
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 14
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 12
239000000203 mixture Substances 0.000 description 9
238000003756 stirring Methods 0.000 description 9
XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 8
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 7
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 7
239000000243 solution Substances 0.000 description 7
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
239000002585 base Substances 0.000 description 6
239000000047 product Substances 0.000 description 6
239000011541 reaction mixture Substances 0.000 description 6
238000001914 filtration Methods 0.000 description 5
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 4
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
229910052786 argon Inorganic materials 0.000 description 4
ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 description 4
125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 4
CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 4
239000011734 sodium Substances 0.000 description 4
229910052708 sodium Inorganic materials 0.000 description 4
206010002660 Anoxia Diseases 0.000 description 3
241000976983 Anoxia Species 0.000 description 3
WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
206010021143 Hypoxia Diseases 0.000 description 3
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
241000699670 Mus sp. Species 0.000 description 3
230000007953 anoxia Effects 0.000 description 3
HRYZWHHZPQKTII-UHFFFAOYSA-N chloroethane Chemical compound CCCl HRYZWHHZPQKTII-UHFFFAOYSA-N 0.000 description 3
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
229910052938 sodium sulfate Inorganic materials 0.000 description 3
235000011152 sodium sulphate Nutrition 0.000 description 3
230000004083 survival effect Effects 0.000 description 3
NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 2
241001465754 Metazoa Species 0.000 description 2
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 2
230000000496 anti-anoxic effect Effects 0.000 description 2
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
NEHMKBQYUWJMIP-UHFFFAOYSA-N chloromethane Chemical compound ClC NEHMKBQYUWJMIP-UHFFFAOYSA-N 0.000 description 2
238000010908 decantation Methods 0.000 description 2
238000000354 decomposition reaction Methods 0.000 description 2
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 2
208000035475 disorder Diseases 0.000 description 2
239000012153 distilled water Substances 0.000 description 2
150000002148 esters Chemical class 0.000 description 2
239000001301 oxygen Substances 0.000 description 2
229910052760 oxygen Inorganic materials 0.000 description 2
239000012071 phase Substances 0.000 description 2
230000000506 psychotropic effect Effects 0.000 description 2
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
150000003254 radicals Chemical class 0.000 description 2
238000010992 reflux Methods 0.000 description 2
239000012312 sodium hydride Substances 0.000 description 2
229910000104 sodium hydride Inorganic materials 0.000 description 2
238000002560 therapeutic procedure Methods 0.000 description 2
235000013311 vegetables Nutrition 0.000 description 2
DZCBKUAAGVVLOX-UHFFFAOYSA-N 1-morpholin-4-ylethanol Chemical compound CC(O)N1CCOCC1 DZCBKUAAGVVLOX-UHFFFAOYSA-N 0.000 description 1
SJZRECIVHVDYJC-UHFFFAOYSA-M 4-hydroxybutyrate Chemical compound OCCCC([O-])=O SJZRECIVHVDYJC-UHFFFAOYSA-M 0.000 description 1
SJZRECIVHVDYJC-UHFFFAOYSA-N 4-hydroxybutyric acid Chemical compound OCCCC(O)=O SJZRECIVHVDYJC-UHFFFAOYSA-N 0.000 description 1
JLLYLQLDYORLBB-UHFFFAOYSA-N 5-bromo-n-methylthiophene-2-sulfonamide Chemical compound CNS(=O)(=O)C1=CC=C(Br)S1 JLLYLQLDYORLBB-UHFFFAOYSA-N 0.000 description 1
208000004998 Abdominal Pain Diseases 0.000 description 1
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 1
VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
FERIUCNNQQJTOY-UHFFFAOYSA-M Butyrate Chemical compound CCCC([O-])=O FERIUCNNQQJTOY-UHFFFAOYSA-M 0.000 description 1
FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Natural products CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 1
UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 1
241001280629 Catharanthus lanceus Species 0.000 description 1
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 1
208000002881 Colic Diseases 0.000 description 1
HTJDQJBWANPRPF-UHFFFAOYSA-N Cyclopropylamine Chemical compound NC1CC1 HTJDQJBWANPRPF-UHFFFAOYSA-N 0.000 description 1
101100441092 Danio rerio crlf3 gene Proteins 0.000 description 1
208000020401 Depressive disease Diseases 0.000 description 1
235000014066 European mistletoe Nutrition 0.000 description 1
241000699666 Mus <mouse, genus> Species 0.000 description 1
206010033799 Paralysis Diseases 0.000 description 1
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
241000208332 Rauvolfia Species 0.000 description 1
235000012300 Rhipsalis cassutha Nutrition 0.000 description 1
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
241000221012 Viscum Species 0.000 description 1
239000004480 active ingredient Substances 0.000 description 1
238000013019 agitation Methods 0.000 description 1
150000001350 alkyl halides Chemical class 0.000 description 1
235000011114 ammonium hydroxide Nutrition 0.000 description 1
239000000935 antidepressant agent Substances 0.000 description 1
229940005513 antidepressants Drugs 0.000 description 1
239000008346 aqueous phase Substances 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
230000003542 behavioural effect Effects 0.000 description 1
230000004071 biological effect Effects 0.000 description 1
210000004556 brain Anatomy 0.000 description 1
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
229910052794 bromium Inorganic materials 0.000 description 1
239000001110 calcium chloride Substances 0.000 description 1
229910001628 calcium chloride Inorganic materials 0.000 description 1
229910052799 carbon Inorganic materials 0.000 description 1
150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
210000003169 central nervous system Anatomy 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
239000012141 concentrate Substances 0.000 description 1
238000001816 cooling Methods 0.000 description 1
230000001054 cortical effect Effects 0.000 description 1
239000013078 crystal Substances 0.000 description 1
HWDVTQAXQJQROO-UHFFFAOYSA-N cyclopropylazanide Chemical compound [NH-]C1CC1 HWDVTQAXQJQROO-UHFFFAOYSA-N 0.000 description 1
125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
238000004821 distillation Methods 0.000 description 1
230000000694 effects Effects 0.000 description 1
239000012259 ether extract Substances 0.000 description 1
125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 description 1
RIFGWPKJUGCATF-UHFFFAOYSA-N ethyl chloroformate Chemical compound CCOC(Cl)=O RIFGWPKJUGCATF-UHFFFAOYSA-N 0.000 description 1
238000001704 evaporation Methods 0.000 description 1
230000008020 evaporation Effects 0.000 description 1
238000000605 extraction Methods 0.000 description 1
159000000011 group IA salts Chemical class 0.000 description 1
229910052736 halogen Inorganic materials 0.000 description 1
150000002367 halogens Chemical class 0.000 description 1
229910052739 hydrogen Inorganic materials 0.000 description 1
208000014674 injury Diseases 0.000 description 1
229940035429 isobutyl alcohol Drugs 0.000 description 1
QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 1
229910052753 mercury Inorganic materials 0.000 description 1
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
229940050176 methyl chloride Drugs 0.000 description 1
XMJHPCRAQCTCFT-UHFFFAOYSA-N methyl chloroformate Chemical compound COC(Cl)=O XMJHPCRAQCTCFT-UHFFFAOYSA-N 0.000 description 1
239000002808 molecular sieve Substances 0.000 description 1
125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 description 1
125000006203 morpholinoethyl group Chemical group [H]C([H])(*)C([H])([H])N1C([H])([H])C([H])([H])OC([H])([H])C1([H])[H] 0.000 description 1
239000012044 organic layer Substances 0.000 description 1
239000012074 organic phase Substances 0.000 description 1
239000008194 pharmaceutical composition Substances 0.000 description 1
239000000546 pharmaceutical excipient Substances 0.000 description 1
230000000144 pharmacologic effect Effects 0.000 description 1
125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
229940072033 potash Drugs 0.000 description 1
239000011591 potassium Substances 0.000 description 1
229910052700 potassium Inorganic materials 0.000 description 1
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Substances [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 1
235000015320 potassium carbonate Nutrition 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
230000001737 promoting effect Effects 0.000 description 1
230000029058 respiratory gaseous exchange Effects 0.000 description 1
238000007127 saponification reaction Methods 0.000 description 1
239000000741 silica gel Substances 0.000 description 1
229910002027 silica gel Inorganic materials 0.000 description 1
URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 1
XYGBKMMCQDZQOZ-UHFFFAOYSA-M sodium;4-hydroxybutanoate Chemical compound [Na+].OCCCC([O-])=O XYGBKMMCQDZQOZ-UHFFFAOYSA-M 0.000 description 1
238000001228 spectrum Methods 0.000 description 1
150000003462 sulfoxides Chemical class 0.000 description 1
230000000287 tissue oxygenation Effects 0.000 description 1
231100000331 toxic Toxicity 0.000 description 1
230000002588 toxic effect Effects 0.000 description 1
230000001988 toxicity Effects 0.000 description 1
231100000419 toxicity Toxicity 0.000 description 1
230000008733 trauma Effects 0.000 description 1
208000009999 tuberous sclerosis Diseases 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/22—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains four or more hetero rings
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/24—Antidepressants
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/26—Psychostimulants, e.g. nicotine, cocaine
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid

Landscapes

Health & Medical Sciences (AREA)
Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Life Sciences & Earth Sciences (AREA)
General Health & Medical Sciences (AREA)
Veterinary Medicine (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Bioinformatics & Cheminformatics (AREA)
Pharmacology & Pharmacy (AREA)
Engineering & Computer Science (AREA)
Animal Behavior & Ethology (AREA)
Public Health (AREA)
Psychiatry (AREA)
Biomedical Technology (AREA)
Neurology (AREA)
Neurosurgery (AREA)
Hematology (AREA)
Diabetes (AREA)
Pain & Pain Management (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)

LU81145A 1978-04-14 1979-04-12 Derives de la tetrahydroalstonine et leur application en therapeutique LU81145A1 (fr)

Applications Claiming Priority (4)

Application Number	Priority Date	Filing Date	Title
FR7811026A FR2422664A1 (fr)	1978-04-14	1978-04-14	Derives de la tetrahydroalstonine et leur application en therapeutique
FR7811026		1978-04-14
FR7906055		1979-03-09
FR7906055A FR2450835A2 (fr)	1978-04-14	1979-03-09	Derives de la tetrahydroalstonine et leur application en therapeutique

Publications (1)

Publication Number	Publication Date
LU81145A1 true LU81145A1 (fr)	1980-12-16

Family

ID=26220552

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
LU81145A LU81145A1 (fr)	1978-04-14	1979-04-12	Derives de la tetrahydroalstonine et leur application en therapeutique

Country Status (14)

Country	Link
JP (1)	JPS54145700A (da)
DE (1)	DE2914805A1 (da)
DK (1)	DK149279A (da)
ES (1)	ES479540A1 (da)
FI (1)	FI791194A7 (da)
FR (1)	FR2450835A2 (da)
GB (1)	GB2018751A (da)
GR (1)	GR66991B (da)
IL (1)	IL57061A0 (da)
IT (1)	IT1111923B (da)
LU (1)	LU81145A1 (da)
NL (1)	NL7902958A (da)
NO (1)	NO791222L (da)
PT (1)	PT69487A (da)

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
FR2451376B1 (fr) *	1979-03-14	1986-04-18	Fabre Sa Pierre	Nouveaux derives tetrahydroalstoniques, leur preparation et leur application en tant que medicaments
BE881050A (fr) *	1980-01-09	1980-07-09	Omnichemue	Nouveaux derives du type oxayohimbane, leur procede d'obtention et medicaments les contenant
FR2539416B1 (fr) *	1983-01-14	1985-09-27	Adir	Nouveaux derives oxindoliques, leur procede de preparation et les compositions pharmaceutiques les renfermant
SE501156C2 (sv) *	1993-04-21	1994-11-28	Ellemtel Utvecklings Ab	Referenssignal sammansatt av klocksignal och synkroniseringssignal, anordning och förfarande för synkronisering m.h.a. referenssignal

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE1225652B (de) *	1961-08-01	1966-09-29	Boehringer & Soehne Gmbh	Verfahren zur Herstellung von in 1-Stellung substituierten 3, 4, 5, 6-Tetrahydroserpentin-derivaten und von deren Salzen

1979
- 1979-03-09 FR FR7906055A patent/FR2450835A2/fr active Granted
- 1979-04-10 NO NO79791222A patent/NO791222L/no unknown
- 1979-04-10 DK DK149279A patent/DK149279A/da not_active IP Right Cessation
- 1979-04-11 FI FI791194A patent/FI791194A7/fi not_active Application Discontinuation
- 1979-04-11 IT IT21793/79A patent/IT1111923B/it active
- 1979-04-11 IL IL57061A patent/IL57061A0/xx unknown
- 1979-04-11 ES ES479540A patent/ES479540A1/es not_active Expired
- 1979-04-11 DE DE19792914805 patent/DE2914805A1/de not_active Withdrawn
- 1979-04-12 NL NL7902958A patent/NL7902958A/xx not_active Application Discontinuation
- 1979-04-12 GR GR58869A patent/GR66991B/el unknown
- 1979-04-12 LU LU81145A patent/LU81145A1/fr unknown
- 1979-04-12 GB GB7912932A patent/GB2018751A/en not_active Withdrawn
- 1979-04-12 PT PT69487A patent/PT69487A/pt unknown
- 1979-04-13 JP JP4595879A patent/JPS54145700A/ja active Pending

Also Published As

Publication number	Publication date
NL7902958A (nl)	1979-10-16
ES479540A1 (es)	1979-07-16
DK149279A (da)	1979-10-15
NO791222L (no)	1979-10-16
FI791194A7 (fi)	1979-10-15
DE2914805A1 (de)	1979-10-18
JPS54145700A (en)	1979-11-14
FR2450835A2 (fr)	1980-10-03
GR66991B (da)	1981-05-18
IL57061A0 (en)	1979-07-25
PT69487A (fr)	1979-05-01
GB2018751A (en)	1979-10-24
IT1111923B (it)	1986-01-13
FR2450835B2 (da)	1982-11-19
IT7921793A0 (it)	1979-04-11

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CH651561A5 (fr)	1985-09-30	Derives des nor-tropane et granatane et leur procede de preparation.
EP0015038B1 (fr)	1984-12-19	Composition pharmaceutique comprenant un dérivé de diphénylhydantoine, dérivés mis en oeuvre et leur préparation
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