DE2062001C2 - 1,2,3,4-Tetrahydro-4-phenylisochinolin-Derivate, deren Säureadditionssalze, Verfahren zu deren Herstellung und pharmazeutisches Präparat - Google Patents
1,2,3,4-Tetrahydro-4-phenylisochinolin-Derivate, deren Säureadditionssalze, Verfahren zu deren Herstellung und pharmazeutisches PräparatInfo
- Publication number
- DE2062001C2 DE2062001C2 DE2062001A DE2062001A DE2062001C2 DE 2062001 C2 DE2062001 C2 DE 2062001C2 DE 2062001 A DE2062001 A DE 2062001A DE 2062001 A DE2062001 A DE 2062001A DE 2062001 C2 DE2062001 C2 DE 2062001C2
- Authority
- DE
- Germany
- Prior art keywords
- tetrahydro
- general formula
- compound
- formula
- rac
- Prior art date
- 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
Links
- 238000000034 method Methods 0.000 title claims description 15
- 230000008569 process Effects 0.000 title claims description 10
- 150000003839 salts Chemical class 0.000 title claims description 8
- 239000002253 acid Substances 0.000 title claims description 4
- 239000000825 pharmaceutical preparation Substances 0.000 title description 4
- 238000004519 manufacturing process Methods 0.000 title description 2
- OSZMNJRKIPAVOS-UHFFFAOYSA-N 4-phenyl-1,2,3,4-tetrahydroisoquinoline Chemical class C1NCC2=CC=CC=C2C1C1=CC=CC=C1 OSZMNJRKIPAVOS-UHFFFAOYSA-N 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims description 47
- 238000002360 preparation method Methods 0.000 claims description 10
- 230000002378 acidificating effect Effects 0.000 claims description 9
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 8
- 229910052799 carbon Inorganic materials 0.000 claims description 3
- SGTJISQIEGVZGI-UHFFFAOYSA-N 4-(3,4-dichlorophenyl)-2-methyl-3,4-dihydro-1h-isoquinolin-7-ol Chemical compound C12=CC=C(O)C=C2CN(C)CC1C1=CC=C(Cl)C(Cl)=C1 SGTJISQIEGVZGI-UHFFFAOYSA-N 0.000 claims description 2
- 125000004423 acyloxy group Chemical group 0.000 claims 1
- 229910052736 halogen Chemical group 0.000 claims 1
- 150000002367 halogens Chemical group 0.000 claims 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 32
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- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 14
- 239000000243 solution Substances 0.000 description 13
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
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- 238000001953 recrystallisation Methods 0.000 description 11
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- 125000004189 3,4-dichlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(Cl)C([H])=C1* 0.000 description 8
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- MDKXBBPLEGPIRI-UHFFFAOYSA-N ethoxyethane;methanol Chemical compound OC.CCOCC MDKXBBPLEGPIRI-UHFFFAOYSA-N 0.000 description 6
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- 238000000338 in vitro Methods 0.000 description 3
- 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 description 3
- 239000012280 lithium aluminium hydride Substances 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
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- UMKZHXUGFJDIQU-UHFFFAOYSA-N 4-(3,4-dichlorophenyl)-7-methoxy-2-propan-2-yl-3,4-dihydro-1h-isoquinoline;hydrochloride Chemical compound Cl.C1N(C(C)C)CC2=CC(OC)=CC=C2C1C1=CC=C(Cl)C(Cl)=C1 UMKZHXUGFJDIQU-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- 229940126062 Compound A Drugs 0.000 description 2
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- NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 description 2
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Chemical compound OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- 239000007868 Raney catalyst Substances 0.000 description 2
- NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 description 2
- 229910000564 Raney nickel Inorganic materials 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 229960000583 acetic acid Drugs 0.000 description 2
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 2
- 229960000836 amitriptyline Drugs 0.000 description 2
- KRMDCWKBEZIMAB-UHFFFAOYSA-N amitriptyline Chemical compound C1CC2=CC=CC=C2C(=CCCN(C)C)C2=CC=CC=C21 KRMDCWKBEZIMAB-UHFFFAOYSA-N 0.000 description 2
- RDHPKYGYEGBMSE-UHFFFAOYSA-N bromoethane Chemical compound CCBr RDHPKYGYEGBMSE-UHFFFAOYSA-N 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 238000000354 decomposition reaction Methods 0.000 description 2
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- 239000008098 formaldehyde solution Substances 0.000 description 2
- AWJUIBRHMBBTKR-UHFFFAOYSA-N isoquinoline Chemical class C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 description 2
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- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
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- LECBDTBWASOEBH-UHFFFAOYSA-N 4-(3,4-dichlorophenyl)-2-ethyl-7-methoxy-3,4-dihydro-1h-isoquinoline;hydrochloride Chemical compound Cl.C12=CC=C(OC)C=C2CN(CC)CC1C1=CC=C(Cl)C(Cl)=C1 LECBDTBWASOEBH-UHFFFAOYSA-N 0.000 description 1
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- 235000012222 talc Nutrition 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- HPGGPRDJHPYFRM-UHFFFAOYSA-J tin(iv) chloride Chemical compound Cl[Sn](Cl)(Cl)Cl HPGGPRDJHPYFRM-UHFFFAOYSA-J 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D217/00—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems
- C07D217/12—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems with radicals, substituted by hetero atoms, attached to carbon atoms of the nitrogen-containing ring
- C07D217/18—Aralkyl radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D217/00—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems
- C07D217/12—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems with radicals, substituted by hetero atoms, attached to carbon atoms of the nitrogen-containing ring
- C07D217/14—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems with radicals, substituted by hetero atoms, attached to carbon atoms of the nitrogen-containing ring other than aralkyl radicals
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Other In-Based Heterocyclic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH10370A CH527194A (de) | 1970-01-06 | 1970-01-06 | Verfahren zur Herstellung von Isochinolin-Derivaten |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE2062001A1 DE2062001A1 (de) | 1971-07-15 |
| DE2062001C2 true DE2062001C2 (de) | 1986-10-16 |
Family
ID=4179328
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2062001A Expired DE2062001C2 (de) | 1970-01-06 | 1970-12-16 | 1,2,3,4-Tetrahydro-4-phenylisochinolin-Derivate, deren Säureadditionssalze, Verfahren zu deren Herstellung und pharmazeutisches Präparat |
Country Status (19)
| Country | Link |
|---|---|
| JP (1) | JPS5515476B1 (en, 2012) |
| AT (1) | AT303041B (en, 2012) |
| BE (1) | BE761219A (en, 2012) |
| CA (1) | CA999866A (en, 2012) |
| CH (2) | CH538477A (en, 2012) |
| DE (1) | DE2062001C2 (en, 2012) |
| DK (1) | DK125021B (en, 2012) |
| ES (1) | ES387016A1 (en, 2012) |
| FI (1) | FI49503C (en, 2012) |
| FR (1) | FR2081412B1 (en, 2012) |
| GB (1) | GB1335261A (en, 2012) |
| IE (1) | IE34859B1 (en, 2012) |
| IL (1) | IL35916A (en, 2012) |
| NL (1) | NL171444C (en, 2012) |
| NO (1) | NO135315C (en, 2012) |
| PH (1) | PH9682A (en, 2012) |
| SE (3) | SE386672B (en, 2012) |
| YU (1) | YU33660B (en, 2012) |
| ZA (1) | ZA708590B (en, 2012) |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US8741901B2 (en) | 2004-07-15 | 2014-06-03 | Albany Molecular Research, Inc. | Aryl- and heteroaryl-substituted tetrahydroisoquinolines and use thereof to block reuptake of norepinephrine, dopamine, and serotonin |
| US8802696B2 (en) | 2009-05-12 | 2014-08-12 | Albany Molecular Research, Inc. | 7-([1,2,4]triazolo[1,5-a]pyridin-6-yl)-4-(3,4-dichlorophenyl)-1,2,3,4-tetrahydroisoqu inoli and use thereof |
| US8815894B2 (en) | 2009-05-12 | 2014-08-26 | Bristol-Myers Squibb Company | Crystalline forms of (S)-7-([1,2,4]triazolo[1,5-a]pyridin-6-yl)-4-(3,4-dichlorophenyl)-1,2,3,4-tetrahydroisoquinoline and use thereof |
| US9034899B2 (en) | 2009-05-12 | 2015-05-19 | Albany Molecular Research, Inc. | Aryl, heteroaryl, and heterocycle substituted tetrahydroisoquinolines and use thereof |
| US9498476B2 (en) | 2008-06-04 | 2016-11-22 | Albany Molecular Research, Inc. | Crystalline form of 6-[(4S)-2-methyl-4-(2-naphthyl)-1,2,3,4-tetrahydroisoquinolin-7-yl]pyridazin-3-amine |
Families Citing this family (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4595688A (en) * | 1983-06-23 | 1986-06-17 | Mcneilab, Inc. | Hexahydropyrrolo[2,1-a]isoquinoline derivatives and antidepressant use thereof |
| US4719216A (en) * | 1983-06-23 | 1988-01-12 | Mcneilab, Inc. | Hexahydropyrrolo(2,1-A)isoquinoline derivatives as antidepressants |
| ZA844402B (en) * | 1983-06-23 | 1986-01-29 | Mcneil Pharmaceutical | Hexahydropyrrolo(2,1-a)isoquinoline derivatives |
| GB2271566A (en) * | 1992-10-14 | 1994-04-20 | Merck & Co Inc | HIV integrase inhibitors |
| US7163949B1 (en) * | 1999-11-03 | 2007-01-16 | Amr Technology, Inc. | 4-phenyl substituted tetrahydroisoquinolines and use thereof |
| NZ519146A (en) * | 1999-11-03 | 2004-02-27 | Albany Molecular Res Inc | 4-phenyl-substituted tetrahydroisoquinolines and use thereof to block reuptake of norepinephrine, dopamine and serotonin |
| DK1246806T3 (da) | 1999-11-03 | 2008-06-16 | Amr Technology Inc | Aryl- og heteroarylsubstituerede tetrahydroisoquinoliner og anvendelse deraf til blokering af genoptagelse af norepinefrin, dopsmin og serotonin |
| EP1113007A1 (en) * | 1999-12-24 | 2001-07-04 | Pfizer Inc. | Tetrahydroisoquinoline compounds as estrogen agonists/antagonists |
| CA2415532C (en) | 2000-07-11 | 2010-05-11 | Albany Molecular Research, Inc. | Novel 4-phenyl substituted tetrahydroisoquinolines therapeutic use thereof |
| PT1899334E (pt) * | 2005-06-17 | 2008-11-06 | Janssen Pharmaceutica Nv | Compostos de naftiridina |
| KR20080044840A (ko) | 2005-07-15 | 2008-05-21 | 에이엠알 테크놀로지, 인크. | 아릴- 및 헤테로아릴-치환된 테트라히드로벤자제핀, 및노르에피네프린, 도파민 및 세로토닌의 재흡수를 차단하기위한 용도 |
| AR071997A1 (es) | 2008-06-04 | 2010-07-28 | Bristol Myers Squibb Co | Forma cristalina de 6-((4s)-2-metil-4-(2-naftil)-1,2,3,4-tetrahidroisoquinolin-7-il)piridazin-3-amina |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1670694B2 (de) * | 1966-05-05 | 1976-07-22 | Hoechst Ag, 6000 Frankfurt | Verfahren zur herstellung von tetrahydroisochinolinen |
-
1970
- 1970-01-06 CH CH1011872A patent/CH538477A/de not_active IP Right Cessation
- 1970-01-06 CH CH10370A patent/CH527194A/de not_active IP Right Cessation
- 1970-12-16 SE SE7313623A patent/SE386672B/xx unknown
- 1970-12-16 SE SE17063/70A patent/SE368401B/xx unknown
- 1970-12-16 DE DE2062001A patent/DE2062001C2/de not_active Expired
- 1970-12-21 ZA ZA708590A patent/ZA708590B/xx unknown
- 1970-12-28 IL IL35916A patent/IL35916A/xx unknown
- 1970-12-29 NL NLAANVRAGE7018956,A patent/NL171444C/xx not_active IP Right Cessation
- 1970-12-31 FI FI703519A patent/FI49503C/fi active
-
1971
- 1971-01-04 IE IE6/71A patent/IE34859B1/xx unknown
- 1971-01-05 NO NO7121A patent/NO135315C/no unknown
- 1971-01-05 AT AT4571A patent/AT303041B/de not_active IP Right Cessation
- 1971-01-05 GB GB45471A patent/GB1335261A/en not_active Expired
- 1971-01-05 BE BE761219A patent/BE761219A/xx not_active IP Right Cessation
- 1971-01-05 ES ES387016A patent/ES387016A1/es not_active Expired
- 1971-01-05 DK DK2571AA patent/DK125021B/da not_active IP Right Cessation
- 1971-01-05 FR FR7100097A patent/FR2081412B1/fr not_active Expired
- 1971-01-06 JP JP7194A patent/JPS5515476B1/ja active Pending
- 1971-01-06 YU YU19/71A patent/YU33660B/xx unknown
- 1971-01-06 CA CA102,060A patent/CA999866A/en not_active Expired
- 1971-01-07 PH PH12087*UA patent/PH9682A/en unknown
-
1973
- 1973-10-05 SE SE7313622A patent/SE399879B/xx unknown
Cited By (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US8741901B2 (en) | 2004-07-15 | 2014-06-03 | Albany Molecular Research, Inc. | Aryl- and heteroaryl-substituted tetrahydroisoquinolines and use thereof to block reuptake of norepinephrine, dopamine, and serotonin |
| US9085531B2 (en) | 2004-07-15 | 2015-07-21 | Albany Molecular Research, Inc. | Aryl- and heteroaryl-substituted tetrahydroisoquinolines and use thereof to block reuptake of norepinephrine, dopamine, and serotonin |
| US9499531B2 (en) | 2004-07-15 | 2016-11-22 | Albany Molecular Research, Inc. | Aryl- and heteroaryl-substituted tetrahydroisoquinolines and use thereof to block reuptake of norepinephrine, dopamine, and serotonin |
| US9498476B2 (en) | 2008-06-04 | 2016-11-22 | Albany Molecular Research, Inc. | Crystalline form of 6-[(4S)-2-methyl-4-(2-naphthyl)-1,2,3,4-tetrahydroisoquinolin-7-yl]pyridazin-3-amine |
| US8802696B2 (en) | 2009-05-12 | 2014-08-12 | Albany Molecular Research, Inc. | 7-([1,2,4]triazolo[1,5-a]pyridin-6-yl)-4-(3,4-dichlorophenyl)-1,2,3,4-tetrahydroisoqu inoli and use thereof |
| US8815894B2 (en) | 2009-05-12 | 2014-08-26 | Bristol-Myers Squibb Company | Crystalline forms of (S)-7-([1,2,4]triazolo[1,5-a]pyridin-6-yl)-4-(3,4-dichlorophenyl)-1,2,3,4-tetrahydroisoquinoline and use thereof |
| US9034899B2 (en) | 2009-05-12 | 2015-05-19 | Albany Molecular Research, Inc. | Aryl, heteroaryl, and heterocycle substituted tetrahydroisoquinolines and use thereof |
| US9173879B2 (en) | 2009-05-12 | 2015-11-03 | Bristol-Myers Squibb Company | Crystalline forms of (S)-7-([1,2,4]triazolo[1,5-a ]pyridin-6-yl)-4-(3,4-dichlorophenyl)-1,2,3,4-tetrahydroisoquinoline and use thereof |
Also Published As
| Publication number | Publication date |
|---|---|
| IE34859L (en) | 1971-07-06 |
| GB1335261A (en) | 1973-10-24 |
| IE34859B1 (en) | 1975-09-03 |
| NL7018956A (en, 2012) | 1971-07-08 |
| CA999866A (en) | 1976-11-16 |
| SE368401B (en, 2012) | 1974-07-01 |
| CH538477A (de) | 1973-06-30 |
| NO135315C (en, 2012) | 1977-03-23 |
| NL171444B (nl) | 1982-11-01 |
| NL171444C (nl) | 1983-04-05 |
| FR2081412B1 (en, 2012) | 1974-04-12 |
| AT303041B (de) | 1972-11-10 |
| CH527194A (de) | 1972-08-31 |
| YU1971A (en) | 1977-06-30 |
| PH9682A (en) | 1976-02-10 |
| FI49503B (en, 2012) | 1975-04-01 |
| FR2081412A1 (en, 2012) | 1971-12-03 |
| ZA708590B (en) | 1971-09-29 |
| IL35916A (en) | 1973-11-28 |
| SE399879B (sv) | 1978-03-06 |
| SE386672B (sv) | 1976-08-16 |
| ES387016A1 (es) | 1976-05-01 |
| FI49503C (fi) | 1975-07-10 |
| DK125021B (da) | 1972-12-18 |
| BE761219A (fr) | 1971-07-05 |
| DE2062001A1 (de) | 1971-07-15 |
| NO135315B (en, 2012) | 1976-12-13 |
| JPS5515476B1 (en, 2012) | 1980-04-23 |
| YU33660B (en) | 1977-12-31 |
| IL35916A0 (en) | 1971-02-25 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| OD | Request for examination | ||
| 8128 | New person/name/address of the agent |
Representative=s name: LEDERER, F., DIPL.-CHEM. DR. MEYER-ROXLAU, R., DIP |
|
| 8128 | New person/name/address of the agent |
Representative=s name: LEDERER, F., DIPL.-CHEM. DR., PAT.-ANW., 8000 MUEN |
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| D2 | Grant after examination | ||
| 8364 | No opposition during term of opposition | ||
| 8339 | Ceased/non-payment of the annual fee |