DE2300519C3 - 4'-Aminomethyl-spiro-[dibenzo (a,d) cycloheptadi-(oder-tri) en-5,2'-dioxolan d'3')] - Derivate, Verfahren zu ihrer Herstellung und diese Verbindungen enthaltende Arzneimittel - Google Patents

4'-Aminomethyl-spiro-[dibenzo (a,d) cycloheptadi-(oder-tri) en-5,2'-dioxolan d'3')] - Derivate, Verfahren zu ihrer Herstellung und diese Verbindungen enthaltende Arzneimittel

Info

Publication number: DE2300519C3
Authority: DE; Germany
Prior art keywords: xiii; tab; compounds; lab; connections
Prior art date: 1972-12-01
Legal status (The legal status 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 status listed.): Expired

Application number

DE19732300519

Other languages

German (de)

English (en)

Other versions

DE2300519B2 (de

DE2300519A1 (de

Inventor

Jeannine Chatou Yvelines Eberle

Claude Paris Fauran

Claude Meudon Hauts-De-Seine Gouret

Guy Paris Raynaud

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Synthelabo SA

Original Assignee

Delalande 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.)

1972-12-01

Filing date

1973-01-05

Publication date

1978-03-02

1972-12-01 Priority claimed from FR7242867A external-priority patent/FR2208650A2/fr

1972-12-05 Priority claimed from FR7243244A external-priority patent/FR2208652A2/fr

1973-01-05 Application filed by Delalande SA filed Critical Delalande SA

1974-06-06 Publication of DE2300519A1 publication Critical patent/DE2300519A1/de

1977-06-23 Publication of DE2300519B2 publication Critical patent/DE2300519B2/de

1978-03-02 Application granted granted Critical

1978-03-02 Publication of DE2300519C3 publication Critical patent/DE2300519C3/de

Status Expired legal-status Critical Current

Links

150000001875 compounds Chemical class 0.000 title claims description 29
238000000034 method Methods 0.000 title description 5
239000003814 drug Substances 0.000 title 1
ICBZSKCTKKUQSY-YUWZRIFDSA-N 4-[(1r,2s)-1-hydroxy-2-(methylamino)propyl]phenol;hydrochloride Chemical compound Cl.CN[C@@H](C)[C@H](O)C1=CC=C(O)C=C1 ICBZSKCTKKUQSY-YUWZRIFDSA-N 0.000 claims description 5
239000000969 carrier Substances 0.000 claims 1
229940126601 medicinal product Drugs 0.000 claims 1
230000004048 modification Effects 0.000 claims 1
238000012986 modification Methods 0.000 claims 1
238000010422 painting Methods 0.000 claims 1
230000000694 effects Effects 0.000 description 17
VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 9
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 9
241000700199 Cavia porcellus Species 0.000 description 4
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
241000699670 Mus sp. Species 0.000 description 4
239000004480 active ingredient Substances 0.000 description 4
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
241001465754 Metazoa Species 0.000 description 3
RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 3
230000004872 arterial blood pressure Effects 0.000 description 3
125000004432 carbon atom Chemical group C* 0.000 description 3
238000002474 experimental method Methods 0.000 description 3
238000010253 intravenous injection Methods 0.000 description 3
239000000243 solution Substances 0.000 description 3
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
241000700198 Cavia Species 0.000 description 2
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
NTYJJOPFIAHURM-UHFFFAOYSA-N Histamine Chemical compound NCCC1=CN=CN1 NTYJJOPFIAHURM-UHFFFAOYSA-N 0.000 description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 2
241000699666 Mus <mouse, genus> Species 0.000 description 2
206010030113 Oedema Diseases 0.000 description 2
NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
208000025865 Ulcer Diseases 0.000 description 2
125000000217 alkyl group Chemical group 0.000 description 2
-1 alkyl radical Chemical class 0.000 description 2
230000001430 anti-depressive effect Effects 0.000 description 2
ZSIQJIWKELUFRJ-UHFFFAOYSA-N azepane Chemical compound C1CCCNCC1 ZSIQJIWKELUFRJ-UHFFFAOYSA-N 0.000 description 2
230000000052 comparative effect Effects 0.000 description 2
238000002347 injection Methods 0.000 description 2
239000007924 injection Substances 0.000 description 2
150000002688 maleic acid derivatives Chemical class 0.000 description 2
239000002609 medium Substances 0.000 description 2
XQYZDYMELSJDRZ-UHFFFAOYSA-N papaverine Chemical compound C1=C(OC)C(OC)=CC=C1CC1=NC=CC2=CC(OC)=C(OC)C=C12 XQYZDYMELSJDRZ-UHFFFAOYSA-N 0.000 description 2
150000003839 salts Chemical class 0.000 description 2
QZAYGJVTTNCVMB-UHFFFAOYSA-N serotonin Chemical compound C1=C(O)C=C2C(CCN)=CNC2=C1 QZAYGJVTTNCVMB-UHFFFAOYSA-N 0.000 description 2
239000000126 substance Substances 0.000 description 2
231100000816 toxic dose Toxicity 0.000 description 2
231100000419 toxicity Toxicity 0.000 description 2
230000001988 toxicity Effects 0.000 description 2
231100000397 ulcer Toxicity 0.000 description 2
230000000304 vasodilatating effect Effects 0.000 description 2
DNXIKVLOVZVMQF-UHFFFAOYSA-N (3beta,16beta,17alpha,18beta,20alpha)-17-hydroxy-11-methoxy-18-[(3,4,5-trimethoxybenzoyl)oxy]-yohimban-16-carboxylic acid, methyl ester Natural products C1C2CN3CCC(C4=CC=C(OC)C=C4N4)=C4C3CC2C(C(=O)OC)C(O)C1OC(=O)C1=CC(OC)=C(OC)C(OC)=C1 DNXIKVLOVZVMQF-UHFFFAOYSA-N 0.000 description 1
GWYPDXLJACEENP-UHFFFAOYSA-N 1,3-cycloheptadiene Chemical compound C1CC=CC=CC1 GWYPDXLJACEENP-UHFFFAOYSA-N 0.000 description 1
229930008281 A03AD01 - Papaverine Natural products 0.000 description 1
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
241000282326 Felis catus Species 0.000 description 1
206010020751 Hypersensitivity Diseases 0.000 description 1
208000001953 Hypotension Diseases 0.000 description 1
206010021118 Hypotonia Diseases 0.000 description 1
208000019695 Migraine disease Diseases 0.000 description 1
208000007101 Muscle Cramp Diseases 0.000 description 1
MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 1
208000008469 Peptic Ulcer Diseases 0.000 description 1
OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
LCQMZZCPPSWADO-UHFFFAOYSA-N Reserpilin Natural products COC(=O)C1COCC2CN3CCc4c([nH]c5cc(OC)c(OC)cc45)C3CC12 LCQMZZCPPSWADO-UHFFFAOYSA-N 0.000 description 1
QEVHRUUCFGRFIF-SFWBKIHZSA-N Reserpine Natural products O=C(OC)[C@@H]1[C@H](OC)[C@H](OC(=O)c2cc(OC)c(OC)c(OC)c2)C[C@H]2[C@@H]1C[C@H]1N(C2)CCc2c3c([nH]c12)cc(OC)cc3 QEVHRUUCFGRFIF-SFWBKIHZSA-N 0.000 description 1
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 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
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
208000005392 Spasm Diseases 0.000 description 1
GUGOEEXESWIERI-UHFFFAOYSA-N Terfenadine Chemical compound C1=CC(C(C)(C)C)=CC=C1C(O)CCCN1CCC(C(O)(C=2C=CC=CC=2)C=2C=CC=CC=2)CC1 GUGOEEXESWIERI-UHFFFAOYSA-N 0.000 description 1
230000007815 allergy Effects 0.000 description 1
230000000202 analgesic effect Effects 0.000 description 1
230000003042 antagnostic effect Effects 0.000 description 1
230000003288 anthiarrhythmic effect Effects 0.000 description 1
230000001387 anti-histamine Effects 0.000 description 1
230000003110 anti-inflammatory effect Effects 0.000 description 1
230000000794 anti-serotonin Effects 0.000 description 1
239000000935 antidepressant agent Substances 0.000 description 1
229940005513 antidepressants Drugs 0.000 description 1
239000000739 antihistaminic agent Substances 0.000 description 1
239000003420 antiserotonin agent Substances 0.000 description 1
WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 1
230000037396 body weight Effects 0.000 description 1
239000002775 capsule Substances 0.000 description 1
229910052799 carbon Inorganic materials 0.000 description 1
238000007596 consolidation process Methods 0.000 description 1
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
208000035475 disorder Diseases 0.000 description 1
239000008298 dragée Substances 0.000 description 1
239000012259 ether extract Substances 0.000 description 1
210000000744 eyelid Anatomy 0.000 description 1
231100000029 gastro-duodenal ulcer Toxicity 0.000 description 1
210000001035 gastrointestinal tract Anatomy 0.000 description 1
210000004907 gland Anatomy 0.000 description 1
239000001963 growth medium Substances 0.000 description 1
244000144980 herd Species 0.000 description 1
229960001340 histamine Drugs 0.000 description 1
208000021822 hypotensive Diseases 0.000 description 1
230000001077 hypotensive effect Effects 0.000 description 1
210000003405 ileum Anatomy 0.000 description 1
230000002757 inflammatory effect Effects 0.000 description 1
238000007912 intraperitoneal administration Methods 0.000 description 1
239000007928 intraperitoneal injection Substances 0.000 description 1
235000021190 leftovers Nutrition 0.000 description 1
239000011976 maleic acid Substances 0.000 description 1
125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 description 1
231100000252 nontoxic Toxicity 0.000 description 1
230000003000 nontoxic effect Effects 0.000 description 1
210000000056 organ Anatomy 0.000 description 1
230000001151 other effect Effects 0.000 description 1
229960001789 papaverine Drugs 0.000 description 1
230000010412 perfusion Effects 0.000 description 1
231100000614 poison Toxicity 0.000 description 1
230000007096 poisonous effect Effects 0.000 description 1
230000009090 positive inotropic effect Effects 0.000 description 1
230000003449 preventive effect Effects 0.000 description 1
150000003141 primary amines Chemical class 0.000 description 1
210000001187 pylorus Anatomy 0.000 description 1
BJOIZNZVOZKDIG-MDEJGZGSSA-N reserpine Chemical compound O([C@H]1[C@@H]([C@H]([C@H]2C[C@@H]3C4=C([C]5C=CC(OC)=CC5=N4)CCN3C[C@H]2C1)C(=O)OC)OC)C(=O)C1=CC(OC)=C(OC)C(OC)=C1 BJOIZNZVOZKDIG-MDEJGZGSSA-N 0.000 description 1
229960003147 reserpine Drugs 0.000 description 1
MDMGHDFNKNZPAU-UHFFFAOYSA-N roserpine Natural products C1C2CN3CCC(C4=CC=C(OC)C=C4N4)=C4C3CC2C(OC(C)=O)C(OC)C1OC(=O)C1=CC(OC)=C(OC)C(OC)=C1 MDMGHDFNKNZPAU-UHFFFAOYSA-N 0.000 description 1
229940076279 serotonin Drugs 0.000 description 1
229910052938 sodium sulfate Inorganic materials 0.000 description 1
235000011152 sodium sulphate Nutrition 0.000 description 1
239000002904 solvent Substances 0.000 description 1
239000007858 starting material Substances 0.000 description 1
239000000829 suppository Substances 0.000 description 1
208000011580 syndromic disease Diseases 0.000 description 1
235000020357 syrup Nutrition 0.000 description 1
239000006188 syrup Substances 0.000 description 1
210000002700 urine Anatomy 0.000 description 1
208000003663 ventricular fibrillation Diseases 0.000 description 1
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
- C07D317/72—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 spiro-condensed with carbocyclic rings

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Heterocyclic Compounds That Contain Two Or More Ring Oxygen Atoms (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)
Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)

DE19732300519 1972-12-01 1973-01-05 4'-Aminomethyl-spiro-[dibenzo (a,d) cycloheptadi-(oder-tri) en-5,2'-dioxolan d'3')] - Derivate, Verfahren zu ihrer Herstellung und diese Verbindungen enthaltende Arzneimittel Expired DE2300519C3 (de)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
FR7242867A FR2208650A2 (en)	1972-12-01	1972-12-01	4'-aminomethyl-spiro(dibenzo(a,d)cycloheptadi(or tri) - ene-5,2' -(1,3)dioxolan)- antidepressants,analgesics,antiinflammatory
FR7243244A FR2208652A2 (en)	1972-12-05	1972-12-05	4'-aminomethyl-spiro(dibenzo(a,d)cycloheptadi(or tri) - ene-5,2' -(1,3)dioxolan)- antidepressants,analgesics,antiinflammatory

Publications (3)

Publication Number	Publication Date
DE2300519A1 DE2300519A1 (de)	1974-06-06
DE2300519B2 DE2300519B2 (de)	1977-06-23
DE2300519C3 true DE2300519C3 (de)	1978-03-02

Family

ID=26217432

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
DE19732300519 Expired DE2300519C3 (de)	1972-12-01	1973-01-05	4'-Aminomethyl-spiro-[dibenzo (a,d) cycloheptadi-(oder-tri) en-5,2'-dioxolan d'3')] - Derivate, Verfahren zu ihrer Herstellung und diese Verbindungen enthaltende Arzneimittel

Country Status (12)

Country	Link
JP (2)	JPS4986369A (sv)
BE (1)	BE793611A (sv)
CA (1)	CA945158A (sv)
CH (1)	CH549012A (sv)
DE (1)	DE2300519C3 (sv)
ES (1)	ES410470A2 (sv)
GB (1)	GB1346163A (sv)
IT (1)	IT1055524B (sv)
LU (1)	LU66795A1 (sv)
NL (1)	NL163513C (sv)
SE (1)	SE395003B (sv)
SU (1)	SU504488A3 (sv)

0
- BE BE793611D patent/BE793611A/xx unknown
1973
- 1973-01-03 CH CH2173A patent/CH549012A/fr not_active IP Right Cessation
- 1973-01-03 GB GB31173A patent/GB1346163A/en not_active Expired
- 1973-01-04 SE SE7300133A patent/SE395003B/sv unknown
- 1973-01-05 LU LU66795A patent/LU66795A1/xx unknown
- 1973-01-05 DE DE19732300519 patent/DE2300519C3/de not_active Expired
- 1973-01-09 ES ES410470A patent/ES410470A2/es not_active Expired
- 1973-01-11 NL NL7300432A patent/NL163513C/xx active
- 1973-01-17 JP JP713173A patent/JPS4986369A/ja active Pending
- 1973-02-05 IT IT6723573A patent/IT1055524B/it active
- 1973-02-21 CA CA164,402*7A patent/CA945158A/en not_active Expired
- 1973-02-27 SU SU1886669A patent/SU504488A3/ru active
1974
- 1974-12-23 JP JP14689574A patent/JPS50140446A/ja active Pending

Also Published As

Publication number	Publication date
NL163513C (nl)	1980-09-15
SE395003B (sv)	1977-07-25
LU66795A1 (sv)	1973-07-18
JPS50140446A (sv)	1975-11-11
BE793611A (fr)	1973-07-02
DE2300519B2 (de)	1977-06-23
GB1346163A (en)	1974-02-06
ES410470A2 (es)	1976-01-01
NL7300432A (sv)	1974-06-05
CA945158A (en)	1974-04-09
SU504488A3 (ru)	1976-02-25
IT1055524B (it)	1982-01-11
DE2300519A1 (de)	1974-06-06
NL163513B (nl)	1980-04-15
JPS4986369A (sv)	1974-08-19
CH549012A (fr)	1974-05-15

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DE2463088C1 (de)	1982-07-15	Substituierte Thienylverbindungen,Verfahren zu ihrer Herstellung und diese Verbindungen enthaltende Arzneimittel
DE2117358C3 (de)	1975-04-17	4'-Aminomethyl-spiro eckige Klammer auf dibenzo eckige Klammer auf a,d eckige Klammer zu cycloheptadi-(oder tri-) en-5,2'-(1 \3'-dioxolan) eckige Klammer zu -Derivate, Verfahren zu deren Herstellung und diese Verbindungen enthaltene Arzneimittel
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DE2300519C3 (de)	1978-03-02	4'-Aminomethyl-spiro-[dibenzo (a,d) cycloheptadi-(oder-tri) en-5,2'-dioxolan d'3')] - Derivate, Verfahren zu ihrer Herstellung und diese Verbindungen enthaltende Arzneimittel
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DE2705949C2 (de)	1983-04-21	4-(Benzoylamino)-piperidinderivate, ein Verfahren zu ihrer Herstellung und diese enthaltende pharmazeutische Mittel
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Legal Events

Date	Code	Title	Description
1978-03-02	C3	Grant after two publication steps (3rd publication)
1982-12-23	8340	Patent of addition ceased/non-payment of fee of main patent