CH622794A5 - - Google Patents

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Info

Publication number: CH622794A5
Authority: CH; Switzerland
Prior art keywords: alkali metal; formula; carbanion; compound; oxygen
Prior art date: 1976-07-13

Application number

CH862677A

Other languages

English (en)

French (fr)

Inventor

Alain Heymes

Original Assignee

Parcor

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.)

1976-07-13

Filing date

1977-07-12

Publication date

1981-04-30

1977-07-12 Application filed by Parcor filed Critical Parcor

1981-04-30 Publication of CH622794A5 publication Critical patent/CH622794A5/fr

Links

238000000034 method Methods 0.000 claims description 15
150000001340 alkali metals Chemical class 0.000 claims description 8
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 8
239000001301 oxygen Substances 0.000 claims description 8
229910052760 oxygen Inorganic materials 0.000 claims description 8
229910052783 alkali metal Inorganic materials 0.000 claims description 7
238000002360 preparation method Methods 0.000 claims description 7
230000008569 process Effects 0.000 claims description 7
-1 alkali metal amide Chemical class 0.000 claims description 6
239000001257 hydrogen Substances 0.000 claims description 5
229910052739 hydrogen Inorganic materials 0.000 claims description 5
MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 claims description 4
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
229910052784 alkaline earth metal Inorganic materials 0.000 claims description 3
150000001412 amines Chemical class 0.000 claims description 3
125000004432 carbon atom Chemical group C* 0.000 claims description 3
239000003638 chemical reducing agent Substances 0.000 claims description 3
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 3
229910000102 alkali metal hydride Inorganic materials 0.000 claims description 2
150000008046 alkali metal hydrides Chemical class 0.000 claims description 2
229910001413 alkali metal ion Inorganic materials 0.000 claims description 2
229910001420 alkaline earth metal ion Inorganic materials 0.000 claims description 2
150000001342 alkaline earth metals Chemical class 0.000 claims description 2
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
150000002432 hydroperoxides Chemical class 0.000 claims description 2
230000003647 oxidation Effects 0.000 claims description 2
238000007254 oxidation reaction Methods 0.000 claims description 2
230000009467 reduction Effects 0.000 claims description 2
150000003839 salts Chemical class 0.000 claims description 2
230000001131 transforming effect Effects 0.000 claims description 2
150000001875 compounds Chemical class 0.000 description 22
241000700159 Rattus Species 0.000 description 11
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
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 description 8
241001465754 Metazoa Species 0.000 description 6
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
238000006243 chemical reaction Methods 0.000 description 6
241000699670 Mus sp. Species 0.000 description 5
230000009471 action Effects 0.000 description 5
230000015572 biosynthetic process Effects 0.000 description 5
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 description 5
241000699666 Mus <mouse, genus> Species 0.000 description 4
241000283973 Oryctolagus cuniculus Species 0.000 description 4
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
230000001054 cortical effect Effects 0.000 description 4
239000000047 product Substances 0.000 description 4
229960002726 vincamine Drugs 0.000 description 4
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
239000002253 acid Substances 0.000 description 3
230000002490 cerebral effect Effects 0.000 description 3
230000000694 effects Effects 0.000 description 3
239000000203 mixture Substances 0.000 description 3
230000000144 pharmacologic effect Effects 0.000 description 3
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
206010048962 Brain oedema Diseases 0.000 description 2
206010065929 Cardiovascular insufficiency Diseases 0.000 description 2
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
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 2
WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 2
150000001204 N-oxides Chemical class 0.000 description 2
WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
230000007059 acute toxicity Effects 0.000 description 2
231100000403 acute toxicity Toxicity 0.000 description 2
150000001408 amides Chemical class 0.000 description 2
239000002585 base Substances 0.000 description 2
230000009286 beneficial effect Effects 0.000 description 2
210000000988 bone and bone Anatomy 0.000 description 2
208000006752 brain edema Diseases 0.000 description 2
230000037213 diet Effects 0.000 description 2
235000005911 diet Nutrition 0.000 description 2
210000001951 dura mater Anatomy 0.000 description 2
230000002496 gastric effect Effects 0.000 description 2
GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 description 2
239000000543 intermediate Substances 0.000 description 2
238000001990 intravenous administration Methods 0.000 description 2
229910052744 lithium Inorganic materials 0.000 description 2
238000004519 manufacturing process Methods 0.000 description 2
229910052757 nitrogen Inorganic materials 0.000 description 2
230000001590 oxidative effect Effects 0.000 description 2
229910052708 sodium Inorganic materials 0.000 description 2
239000011734 sodium Substances 0.000 description 2
239000002904 solvent Substances 0.000 description 2
230000000638 stimulation Effects 0.000 description 2
238000003786 synthesis reaction Methods 0.000 description 2
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
230000001225 therapeutic effect Effects 0.000 description 2
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 description 1
150000004052 8-membered heterocyclic compounds Chemical class 0.000 description 1
101150041968 CDC13 gene Proteins 0.000 description 1
UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 1
241000282472 Canis lupus familiaris Species 0.000 description 1
GIGFIWJRTMBSRP-UHFFFAOYSA-N DL-Vincadifformin Natural products C1C(C(=O)OC)=C2NC3=CC=CC=C3C22CCN3CCCC1(CC)C23 GIGFIWJRTMBSRP-UHFFFAOYSA-N 0.000 description 1
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
206010019196 Head injury Diseases 0.000 description 1
206010019909 Hernia Diseases 0.000 description 1
206010021143 Hypoxia Diseases 0.000 description 1
206010030113 Oedema Diseases 0.000 description 1
229910019020 PtO2 Inorganic materials 0.000 description 1
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
KILNDJCLJBOWAN-UHFFFAOYSA-N Tabersonine Natural products CCC12CC(=C3N(C)c4cc(OC)ccc4C35CCN(CC=C1)C25)C(=O)OC KILNDJCLJBOWAN-UHFFFAOYSA-N 0.000 description 1
HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 1
238000010521 absorption reaction Methods 0.000 description 1
125000003668 acetyloxy group Chemical group [H]C([H])([H])C(=O)O[*] 0.000 description 1
239000004480 active ingredient Substances 0.000 description 1
230000001154 acute effect Effects 0.000 description 1
YKIOKAURTKXMSB-UHFFFAOYSA-N adams's catalyst Chemical compound O=[Pt]=O YKIOKAURTKXMSB-UHFFFAOYSA-N 0.000 description 1
150000001298 alcohols Chemical class 0.000 description 1
150000001335 aliphatic alkanes Chemical class 0.000 description 1
239000003513 alkali Substances 0.000 description 1
238000004458 analytical method Methods 0.000 description 1
210000000576 arachnoid Anatomy 0.000 description 1
150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
230000008901 benefit Effects 0.000 description 1
230000037396 body weight Effects 0.000 description 1
235000021152 breakfast Nutrition 0.000 description 1
239000001110 calcium chloride Substances 0.000 description 1
229910001628 calcium chloride Inorganic materials 0.000 description 1
239000002775 capsule Substances 0.000 description 1
239000003054 catalyst Substances 0.000 description 1
238000009903 catalytic hydrogenation reaction Methods 0.000 description 1
125000001309 chloro group Chemical class Cl* 0.000 description 1
238000004587 chromatography analysis Methods 0.000 description 1
230000007665 chronic toxicity Effects 0.000 description 1
231100000160 chronic toxicity Toxicity 0.000 description 1
239000012043 crude product Substances 0.000 description 1
230000003111 delayed effect Effects 0.000 description 1
230000000916 dilatatory effect Effects 0.000 description 1
206010013395 disorientation Diseases 0.000 description 1
239000003814 drug Substances 0.000 description 1
230000002497 edematous effect Effects 0.000 description 1
230000037406 food intake Effects 0.000 description 1
239000007789 gas Substances 0.000 description 1
229930195733 hydrocarbon Natural products 0.000 description 1
150000002430 hydrocarbons Chemical class 0.000 description 1
WQYVRQLZKVEZGA-UHFFFAOYSA-N hypochlorite Inorganic materials Cl[O-] WQYVRQLZKVEZGA-UHFFFAOYSA-N 0.000 description 1
230000007954 hypoxia Effects 0.000 description 1
230000006872 improvement Effects 0.000 description 1
150000002475 indoles Chemical class 0.000 description 1
239000011261 inert gas Substances 0.000 description 1
229940102223 injectable solution Drugs 0.000 description 1
230000013016 learning Effects 0.000 description 1
231100000225 lethality Toxicity 0.000 description 1
JILPJDVXYVTZDQ-UHFFFAOYSA-N lithium methoxide Chemical compound [Li+].[O-]C JILPJDVXYVTZDQ-UHFFFAOYSA-N 0.000 description 1
CRGZYKWWYNQGEC-UHFFFAOYSA-N magnesium;methanolate Chemical compound [Mg+2].[O-]C.[O-]C CRGZYKWWYNQGEC-UHFFFAOYSA-N 0.000 description 1
235000012054 meals Nutrition 0.000 description 1
230000015654 memory Effects 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
210000001640 nerve ending Anatomy 0.000 description 1
230000001537 neural effect Effects 0.000 description 1
125000004433 nitrogen atom Chemical group N* 0.000 description 1
230000036441 nociceptive stimulation Effects 0.000 description 1
229940100688 oral solution Drugs 0.000 description 1
239000012074 organic phase Substances 0.000 description 1
230000004783 oxidative metabolism Effects 0.000 description 1
125000004430 oxygen atom Chemical group O* 0.000 description 1
238000007911 parenteral administration Methods 0.000 description 1
AQSJGOWTSHOLKH-UHFFFAOYSA-N phosphite(3-) Chemical class [O-]P([O-])[O-] AQSJGOWTSHOLKH-UHFFFAOYSA-N 0.000 description 1
230000000704 physical effect Effects 0.000 description 1
BDAWXSQJJCIFIK-UHFFFAOYSA-N potassium methoxide Chemical compound [K+].[O-]C BDAWXSQJJCIFIK-UHFFFAOYSA-N 0.000 description 1
LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
230000009257 reactivity Effects 0.000 description 1
238000011084 recovery Methods 0.000 description 1
230000002336 repolarization Effects 0.000 description 1
239000000523 sample Substances 0.000 description 1
239000000741 silica gel Substances 0.000 description 1
229910002027 silica gel Inorganic materials 0.000 description 1
210000003625 skull Anatomy 0.000 description 1
229910000104 sodium hydride Inorganic materials 0.000 description 1
239000012312 sodium hydride Substances 0.000 description 1
CGRKYEALWSRNJS-UHFFFAOYSA-N sodium;2-methylbutan-2-olate Chemical compound [Na+].CCC(C)(C)[O-] CGRKYEALWSRNJS-UHFFFAOYSA-N 0.000 description 1
230000002269 spontaneous effect Effects 0.000 description 1
229910001220 stainless steel Inorganic materials 0.000 description 1
239000010935 stainless steel Substances 0.000 description 1
238000007920 subcutaneous administration Methods 0.000 description 1
239000000829 suppository Substances 0.000 description 1
230000004083 survival effect Effects 0.000 description 1
239000000725 suspension Substances 0.000 description 1
208000024891 symptom Diseases 0.000 description 1
208000011580 syndromic disease Diseases 0.000 description 1
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 description 1
230000003390 teratogenic effect Effects 0.000 description 1
210000000115 thoracic cavity Anatomy 0.000 description 1
231100000331 toxic Toxicity 0.000 description 1
230000002588 toxic effect Effects 0.000 description 1
231100000419 toxicity Toxicity 0.000 description 1
230000001988 toxicity Effects 0.000 description 1
230000002110 toxicologic effect Effects 0.000 description 1
231100000027 toxicology Toxicity 0.000 description 1
231100000041 toxicology testing Toxicity 0.000 description 1
CYTQBVOFDCPGCX-UHFFFAOYSA-N trimethyl phosphite Chemical compound COP(OC)OC CYTQBVOFDCPGCX-UHFFFAOYSA-N 0.000 description 1
208000019553 vascular disease Diseases 0.000 description 1
125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
238000005303 weighing Methods 0.000 description 1
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 description 1
239000008096 xylene Substances 0.000 description 1
150000003738 xylenes Chemical class 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/12—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains three hetero rings
- C07D471/20—Spiro-condensed systems
- 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
- A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00

Landscapes

Organic Chemistry (AREA)
Chemical & Material Sciences (AREA)
Health & Medical Sciences (AREA)
Bioinformatics & Cheminformatics (AREA)
Engineering & Computer Science (AREA)
Life Sciences & Earth Sciences (AREA)
Veterinary Medicine (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
General Chemical & Material Sciences (AREA)
Pharmacology & Pharmacy (AREA)
Chemical Kinetics & Catalysis (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Medicinal Chemistry (AREA)
Biomedical Technology (AREA)
Neurosurgery (AREA)
Neurology (AREA)
Hospice & Palliative Care (AREA)
Psychiatry (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)
Preparation Of Compounds By Using Micro-Organisms (AREA)

CH862677A 1976-07-13 1977-07-12 CH622794A5 (de)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
FR7621431A FR2358147A1 (fr)	1976-07-13	1976-07-13	Aspidospermidines

Publications (1)

Publication Number	Publication Date
CH622794A5 true CH622794A5 (de)	1981-04-30

Family

ID=9175673

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CH862677A CH622794A5 (de)	1976-07-13	1977-07-12

Country Status (17)

Country	Link
US (1)	US4152519A (de)
JP (1)	JPS539798A (de)
AT (1)	AT358189B (de)
AU (1)	AU512242B2 (de)
BE (1)	BE856722A (de)
BR (1)	BR7704588A (de)
CA (1)	CA1085848A (de)
CH (1)	CH622794A5 (de)
DE (1)	DE2731481A1 (de)
ES (1)	ES460400A1 (de)
FR (1)	FR2358147A1 (de)
GB (1)	GB1546308A (de)
IT (1)	IT1081020B (de)
LU (1)	LU77727A1 (de)
NL (1)	NL7707721A (de)
NZ (1)	NZ184636A (de)
ZA (1)	ZA774039B (de)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
FR2439200A2 (fr) *	1978-10-19	1980-05-16	Sandoz Sa	Nouveaux derives de la 1,2-didehydro-aspidospermidine, leur preparation et leur application comme medicaments
HU206883B (en) *	1990-12-18	1993-01-28	Richter Gedeon Vegyeszet	Process for producing new 15-nitro-2-beta-, 3-beta-dihydro- and 15-nitro-2-beta, 3-beta-, 6,7-tetrahydro-tabersonin derivatives and pharmaceutical compositions containing them

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
BE763730R (fr) *	1971-01-15	1971-08-02	Omnium Chimique Sa	Procede de preparation de la vincamine naturelle a partir de latabersonine et derives indoliques
BE765427A (fr) *	1971-04-07	1971-08-30	Omnium Chimique Sa	Procede de preparation de la vincine naturelle a partir de la (-) mehtoxy-11-tabersonine et derives indoliques nouveaux.
BE765795A (fr) *	1971-04-15	1971-08-30	Omnium Chimique Sa	Procede de preparation d'inverses optiques de la vincamine naturelle etderives indoliques nouveaux.
US3987048A (en) *	1973-06-22	1976-10-19	Omnium Chimique Societe Anonyme	Process for the preparation of vincadifformine and derivatives

1976
- 1976-07-13 FR FR7621431A patent/FR2358147A1/fr active Granted
1977
- 1977-06-23 CA CA281,276A patent/CA1085848A/fr not_active Expired
- 1977-07-05 ZA ZA00774039A patent/ZA774039B/xx unknown
- 1977-07-05 ES ES460400A patent/ES460400A1/es not_active Expired
- 1977-07-07 US US05/813,670 patent/US4152519A/en not_active Expired - Lifetime
- 1977-07-11 LU LU77727A patent/LU77727A1/xx unknown
- 1977-07-12 AU AU26947/77A patent/AU512242B2/en not_active Expired
- 1977-07-12 DE DE19772731481 patent/DE2731481A1/de not_active Ceased
- 1977-07-12 IT IT12681/77A patent/IT1081020B/it active
- 1977-07-12 BE BE179265A patent/BE856722A/xx not_active IP Right Cessation
- 1977-07-12 CH CH862677A patent/CH622794A5/fr not_active IP Right Cessation
- 1977-07-12 NL NL7707721A patent/NL7707721A/xx not_active Application Discontinuation
- 1977-07-12 AT AT500077A patent/AT358189B/de not_active IP Right Cessation
- 1977-07-12 GB GB29234/77A patent/GB1546308A/en not_active Expired
- 1977-07-13 JP JP8399277A patent/JPS539798A/ja active Pending
- 1977-07-13 NZ NZ184636A patent/NZ184636A/xx unknown
- 1977-07-13 BR BR7704588A patent/BR7704588A/pt unknown

Also Published As

Publication number	Publication date
GB1546308A (en)	1979-05-23
US4152519A (en)	1979-05-01
JPS539798A (en)	1978-01-28
AT358189B (de)	1980-08-25
LU77727A1 (de)	1977-10-07
ES460400A1 (es)	1978-05-01
NZ184636A (en)	1980-04-28
ZA774039B (en)	1978-05-30
BR7704588A (pt)	1978-04-04
NL7707721A (nl)	1978-01-17
DE2731481A1 (de)	1978-01-19
CA1085848A (fr)	1980-09-16
FR2358147B1 (de)	1978-12-15
BE856722A (fr)	1978-01-12
IT1081020B (it)	1985-05-16
ATA500077A (de)	1980-01-15
AU2694777A (en)	1979-01-18
AU512242B2 (en)	1980-10-02
FR2358147A1 (fr)	1978-02-10

Legal Events

Date	Code	Title	Description
1984-03-30	PL	Patent ceased
2024-10-31	PL	Patent ceased

Publication	Publication Date	Title
CH635813A5 (fr)	1983-04-29	1,9-dihydroxyoctahydrophenanthrenes et medicament les contenant.
EP0012643A2 (de)	1980-06-25	1-Phenyl-3-(4-piperidyl)-propan-1-on-Derivate, Verfahren zu ihrer Herstellung und die enthaltende pharmazeutische Zusammensetzungen
EP0046707A1 (de)	1982-03-03	4-Aminobuttersäure-Derivate und diese enthaltende, insbesondere auf das Zentralnervensystem wirksame, Arzneimittel
CA2127066A1 (fr)	1994-12-31	Derives d'.alpha. amino acides leur procede de preparation et les compositions pharmaceutiques qui les contiennent
BE1008622A3 (fr)	1996-06-04	Derives de l'epi-epibatidine.
CH622794A5 (de)	1981-04-30
EP0063084A1 (de)	1982-10-20	Phenethanolamin-Derivate, Verfahren zu ihrer Herstellung und ihre Verwendung als Arzneimittel
US3723514A (en)	1973-03-27	(-)threo-3-(4-hydroxy-3-methoxyphenyl)-serine
EP0078765B1 (de)	1986-02-26	P-Acylamino-Phenol-Derivate mit therapeutischem Effekt, Verfahren zu deren Herstellung und Zusammensetzung mit therapeutischem Effekt, diese Derivate als pharmakologische aktive Ingredienzen enthaltend
CA1167444A (fr)	1984-05-15	Derives de la chloro-3 quinoleine, procedes pour leur preparation, et leur utilisation comme medicaments
EP0027412B1 (de)	1983-12-14	Pyridin-Derivate, Verfahren zu ihrer Herstellung und sie enthaltende Arzneimittel
EP0228314A2 (de)	1987-07-08	Verwendung von Äthanolamin-derivaten zur Behandlung oder Prävention von Hyperlipämie
EP0022407B1 (de)	1982-04-21	Cyclophosphathiazene, Verfahren zu ihrer Herstellung und diese enthaltende Mittel
EP0138684A2 (de)	1985-04-24	2-(N-Pyrrolidino)-3-isobutoxy-N-phenyl substituierte N-Benzylpropylamine, ihre Herstellung und ihre pharmazeutische Anwendung
FR2846654A1 (fr)	2004-05-07	Nouveaux derives de la 2,3-dihydro-4(1h)-pyridinone, leur procede de preparation et les compositions pharmaceutiques qui les contiennent
EP0082040B1 (de)	1986-01-15	3,7a-Diazacyclohepta(j,k)fluorenderivate, ihre Herstellung und ihre therapeutische Verwendung
EP0412898A1 (de)	1991-02-13	Oxazolopyridinderivate, Verfahren zu ihrer Herstellung und diese enthaltende pharmazeutische Zubereitungen
GB2081270A (en)	1982-02-17	Phosphonium salts
CH647503A5 (fr)	1985-01-31	Derives de la 16-methoxy-16-methyl-prostaglandine e(1), procede pour leur synthese et medicaments gastro-protecteurs contenant lesdits derives.
EP0047207A1 (de)	1982-03-10	N-(1-allyl-2-pyrrolidinyl-methyl)-2-methoxy-4-amino-5-methylsulfamoyl-benzamide, Verfahren zur Herstellung und Verwendung als Heilmittel
BE862019R (fr)	1978-06-19	Nouveaux derives de la vincamine, leur preparation et leur application comme medicaments
JPS6112660A (ja)	1986-01-21	新規２−ピロリドン誘導体及び抗炎症剤
EP0569276B1 (de)	1997-01-29	Neue Verwendung von (S) Amino-2-dichloro-3,4-benzyl)-2-propanol-1 Enantiomere Derivate
EP0035945A2 (de)	1981-09-16	Acylguanidine, Harnstoffe und substituierte Harnstoffe, Verfahren zu ihrer Herstellung und ihre Verwendung als Arzneimittel
US4748274A (en)	1988-05-31	4-hydroxy-4-(substituted alkenyl)cyclohexanecarboxylic acids