DE60029131T2 - Verwendung von 1-aminoindanderivaten zur behandlung der manie in verbindung mit manisch-depressiver erkrankung - Google Patents
Verwendung von 1-aminoindanderivaten zur behandlung der manie in verbindung mit manisch-depressiver erkrankung Download PDFInfo
- Publication number
- DE60029131T2 DE60029131T2 DE60029131T DE60029131T DE60029131T2 DE 60029131 T2 DE60029131 T2 DE 60029131T2 DE 60029131 T DE60029131 T DE 60029131T DE 60029131 T DE60029131 T DE 60029131T DE 60029131 T2 DE60029131 T2 DE 60029131T2
- Authority
- DE
- Germany
- Prior art keywords
- alkyl
- salt
- hydrogen
- use according
- substituted
- 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 - Lifetime
Links
- 208000028683 bipolar I disease Diseases 0.000 title claims description 10
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 title claims description 5
- XJEVHMGJSYVQBQ-UHFFFAOYSA-N 2,3-dihydro-1h-inden-1-amine Chemical class C1=CC=C2C(N)CCC2=C1 XJEVHMGJSYVQBQ-UHFFFAOYSA-N 0.000 title abstract description 8
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 20
- 239000001257 hydrogen Substances 0.000 claims abstract description 20
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims abstract description 19
- 206010026749 Mania Diseases 0.000 claims abstract description 16
- 150000003839 salts Chemical class 0.000 claims abstract description 14
- 239000000203 mixture Substances 0.000 claims abstract description 9
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 4
- 150000002367 halogens Chemical class 0.000 claims abstract description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 4
- 125000003392 indanyl group Chemical group C1(CCC2=CC=CC=C12)* 0.000 claims abstract description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 4
- DBGKPDNKZZGWOM-JTQLQIEISA-N n-[(1s)-2,3-dihydro-1h-inden-1-yl]formamide Chemical compound C1=CC=C2[C@@H](NC=O)CCC2=C1 DBGKPDNKZZGWOM-JTQLQIEISA-N 0.000 claims description 31
- UOOXDDHYFFXMJJ-LLVKDONJSA-N n-[(1r)-2,3-dihydro-1h-inden-1-yl]acetamide Chemical compound C1=CC=C2[C@H](NC(=O)C)CCC2=C1 UOOXDDHYFFXMJJ-LLVKDONJSA-N 0.000 claims description 25
- 150000001875 compounds Chemical class 0.000 claims description 23
- BKAZIFPIBFUJFU-UHFFFAOYSA-N 2-amino-n-(2,3-dihydro-1h-inden-1-yl)acetamide Chemical compound C1=CC=C2C(NC(=O)CN)CCC2=C1 BKAZIFPIBFUJFU-UHFFFAOYSA-N 0.000 claims description 21
- 239000003814 drug Substances 0.000 claims description 13
- 229940079593 drug Drugs 0.000 claims description 9
- 238000007912 intraperitoneal administration Methods 0.000 claims description 9
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 7
- 125000003118 aryl group Chemical group 0.000 claims description 7
- 125000000217 alkyl group Chemical group 0.000 claims description 6
- QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 4
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical class CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims description 2
- CCIVGXIOQKPBKL-UHFFFAOYSA-N ethanesulfonic acid Chemical class CCS(O)(=O)=O CCIVGXIOQKPBKL-UHFFFAOYSA-N 0.000 claims description 2
- 150000003467 sulfuric acid derivatives Chemical class 0.000 claims description 2
- 230000000699 topical effect Effects 0.000 claims description 2
- 150000002431 hydrogen Chemical class 0.000 claims 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 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 abstract description 7
- 208000020925 Bipolar disease Diseases 0.000 abstract description 3
- 125000004400 (C1-C12) alkyl group Chemical group 0.000 abstract 3
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 abstract 3
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 abstract 1
- 230000000694 effects Effects 0.000 description 50
- 241000700159 Rattus Species 0.000 description 31
- BKAZIFPIBFUJFU-JTQLQIEISA-N 2-amino-N-[(1S)-2,3-dihydro-1H-inden-1-yl]acetamide Chemical compound C1CC2=CC=CC=C2[C@H]1NC(=O)CN BKAZIFPIBFUJFU-JTQLQIEISA-N 0.000 description 13
- 238000002474 experimental method Methods 0.000 description 12
- KWTSXDURSIMDCE-QMMMGPOBSA-N (S)-amphetamine Chemical compound C[C@H](N)CC1=CC=CC=C1 KWTSXDURSIMDCE-QMMMGPOBSA-N 0.000 description 11
- 229940025084 amphetamine Drugs 0.000 description 11
- 230000006742 locomotor activity Effects 0.000 description 11
- 238000000540 analysis of variance Methods 0.000 description 8
- 230000000857 drug effect Effects 0.000 description 7
- 230000001550 time effect Effects 0.000 description 7
- 208000013403 hyperactivity Diseases 0.000 description 6
- 230000003993 interaction Effects 0.000 description 6
- 238000012360 testing method Methods 0.000 description 6
- 238000013105 post hoc analysis Methods 0.000 description 5
- 230000003001 depressive effect Effects 0.000 description 4
- 230000036651 mood Effects 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- 229940123685 Monoamine oxidase inhibitor Drugs 0.000 description 3
- 210000003169 central nervous system Anatomy 0.000 description 3
- 238000005259 measurement Methods 0.000 description 3
- 239000002899 monoamine oxidase inhibitor Substances 0.000 description 3
- -1 C 1 -C 4 alkyl Chemical class 0.000 description 2
- 206010010904 Convulsion Diseases 0.000 description 2
- 208000020401 Depressive disease Diseases 0.000 description 2
- 206010022998 Irritability Diseases 0.000 description 2
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 2
- 241001465754 Metazoa Species 0.000 description 2
- 102000010909 Monoamine Oxidase Human genes 0.000 description 2
- 108010062431 Monoamine oxidase Proteins 0.000 description 2
- 208000018737 Parkinson disease Diseases 0.000 description 2
- 208000028017 Psychotic disease Diseases 0.000 description 2
- 208000030886 Traumatic Brain injury Diseases 0.000 description 2
- 230000003561 anti-manic effect Effects 0.000 description 2
- 239000000935 antidepressant agent Substances 0.000 description 2
- 229940005513 antidepressants Drugs 0.000 description 2
- 238000009227 behaviour therapy Methods 0.000 description 2
- 230000036461 convulsion Effects 0.000 description 2
- 239000003112 inhibitor Substances 0.000 description 2
- 238000002347 injection Methods 0.000 description 2
- 239000007924 injection Substances 0.000 description 2
- 229910052744 lithium Inorganic materials 0.000 description 2
- 230000003137 locomotive effect Effects 0.000 description 2
- BQJCRHHNABKAKU-KBQPJGBKSA-N morphine Chemical compound O([C@H]1[C@H](C=C[C@H]23)O)C4=C5[C@@]12CCN(C)[C@@H]3CC5=CC=C4O BQJCRHHNABKAKU-KBQPJGBKSA-N 0.000 description 2
- 239000002547 new drug Substances 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- AQHHHDLHHXJYJD-UHFFFAOYSA-N propranolol Chemical compound C1=CC=C2C(OCC(O)CNC(C)C)=CC=CC2=C1 AQHHHDLHHXJYJD-UHFFFAOYSA-N 0.000 description 2
- 238000007920 subcutaneous administration Methods 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- XJEVHMGJSYVQBQ-SECBINFHSA-N (1r)-2,3-dihydro-1h-inden-1-amine Chemical compound C1=CC=C2[C@H](N)CCC2=C1 XJEVHMGJSYVQBQ-SECBINFHSA-N 0.000 description 1
- SGTNSNPWRIOYBX-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-{[2-(3,4-dimethoxyphenyl)ethyl](methyl)amino}-2-(propan-2-yl)pentanenitrile Chemical compound C1=C(OC)C(OC)=CC=C1CCN(C)CCCC(C#N)(C(C)C)C1=CC=C(OC)C(OC)=C1 SGTNSNPWRIOYBX-UHFFFAOYSA-N 0.000 description 1
- LMHHFZAXSANGGM-UHFFFAOYSA-N 2-aminoindane Chemical compound C1=CC=C2CC(N)CC2=C1 LMHHFZAXSANGGM-UHFFFAOYSA-N 0.000 description 1
- MAYMVHAVYDCEHG-UHFFFAOYSA-N 3-amino-2,3-dihydro-1h-inden-4-ol Chemical class C1=CC(O)=C2C(N)CCC2=C1 MAYMVHAVYDCEHG-UHFFFAOYSA-N 0.000 description 1
- GJSURZIOUXUGAL-UHFFFAOYSA-N Clonidine Chemical compound ClC1=CC=CC(Cl)=C1NC1=NCCN1 GJSURZIOUXUGAL-UHFFFAOYSA-N 0.000 description 1
- 206010012289 Dementia Diseases 0.000 description 1
- HCYAFALTSJYZDH-UHFFFAOYSA-N Desimpramine Chemical compound C1CC2=CC=CC=C2N(CCCNC)C2=CC=CC=C21 HCYAFALTSJYZDH-UHFFFAOYSA-N 0.000 description 1
- 206010059866 Drug resistance Diseases 0.000 description 1
- 206010019075 Hallucination, visual Diseases 0.000 description 1
- 208000004547 Hallucinations Diseases 0.000 description 1
- 206010020400 Hostility Diseases 0.000 description 1
- 206010020710 Hyperphagia Diseases 0.000 description 1
- 208000019022 Mood disease Diseases 0.000 description 1
- 206010027951 Mood swings Diseases 0.000 description 1
- 241000283984 Rodentia Species 0.000 description 1
- 208000013738 Sleep Initiation and Maintenance disease Diseases 0.000 description 1
- 208000032140 Sleepiness Diseases 0.000 description 1
- 206010041349 Somnolence Diseases 0.000 description 1
- 102000030621 adenylate cyclase Human genes 0.000 description 1
- 108060000200 adenylate cyclase Proteins 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 230000003444 anaesthetic effect Effects 0.000 description 1
- 239000002269 analeptic agent Substances 0.000 description 1
- 230000003266 anti-allergic effect Effects 0.000 description 1
- 230000001773 anti-convulsant effect Effects 0.000 description 1
- 230000001430 anti-depressive effect Effects 0.000 description 1
- 230000003110 anti-inflammatory effect Effects 0.000 description 1
- 239000001961 anticonvulsive agent Substances 0.000 description 1
- 229960003965 antiepileptics Drugs 0.000 description 1
- 239000002249 anxiolytic agent Substances 0.000 description 1
- 230000000949 anxiolytic effect Effects 0.000 description 1
- 230000036528 appetite Effects 0.000 description 1
- 235000019789 appetite Nutrition 0.000 description 1
- 230000037007 arousal Effects 0.000 description 1
- 230000003542 behavioural effect Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 208000022257 bipolar II disease Diseases 0.000 description 1
- 210000004204 blood vessel Anatomy 0.000 description 1
- 229960000623 carbamazepine Drugs 0.000 description 1
- FFGPTBGBLSHEPO-UHFFFAOYSA-N carbamazepine Chemical compound C1=CC2=CC=CC=C2N(C(=O)N)C2=CC=CC=C21 FFGPTBGBLSHEPO-UHFFFAOYSA-N 0.000 description 1
- 150000003943 catecholamines Chemical class 0.000 description 1
- 230000001966 cerebroprotective effect Effects 0.000 description 1
- ANTSCNMPPGJYLG-UHFFFAOYSA-N chlordiazepoxide Chemical compound O=N=1CC(NC)=NC2=CC=C(Cl)C=C2C=1C1=CC=CC=C1 ANTSCNMPPGJYLG-UHFFFAOYSA-N 0.000 description 1
- 229960004782 chlordiazepoxide Drugs 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 229960002896 clonidine Drugs 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 239000008367 deionised water Substances 0.000 description 1
- 229910021641 deionized water Inorganic materials 0.000 description 1
- 229960003914 desipramine Drugs 0.000 description 1
- NIJJYAXOARWZEE-UHFFFAOYSA-N di-n-propyl-acetic acid Natural products CCCC(C(O)=O)CCC NIJJYAXOARWZEE-UHFFFAOYSA-N 0.000 description 1
- 230000000916 dilatatory effect Effects 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 238000001647 drug administration Methods 0.000 description 1
- 206010015037 epilepsy Diseases 0.000 description 1
- 239000002360 explosive Substances 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 206010022437 insomnia Diseases 0.000 description 1
- 229910003002 lithium salt Inorganic materials 0.000 description 1
- 159000000002 lithium salts Chemical class 0.000 description 1
- 239000003589 local anesthetic agent Substances 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 229920000609 methyl cellulose Polymers 0.000 description 1
- 239000001923 methylcellulose Substances 0.000 description 1
- 229960005181 morphine Drugs 0.000 description 1
- 101150006061 neur gene Proteins 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 235000020830 overeating Nutrition 0.000 description 1
- 230000001575 pathological effect Effects 0.000 description 1
- 229960003712 propranolol Drugs 0.000 description 1
- 229940001470 psychoactive drug Drugs 0.000 description 1
- 239000004089 psychotropic agent Substances 0.000 description 1
- 230000000384 rearing effect Effects 0.000 description 1
- 208000037922 refractory disease Diseases 0.000 description 1
- 238000011808 rodent model Methods 0.000 description 1
- 230000001932 seasonal effect Effects 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 238000012453 sprague-dawley rat model Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000007619 statistical method Methods 0.000 description 1
- 238000009120 supportive therapy Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- MSRILKIQRXUYCT-UHFFFAOYSA-M valproate semisodium Chemical compound [Na+].CCCC(C(O)=O)CCC.CCCC(C([O-])=O)CCC MSRILKIQRXUYCT-UHFFFAOYSA-M 0.000 description 1
- 229960000604 valproic acid Drugs 0.000 description 1
- 230000000304 vasodilatating effect Effects 0.000 description 1
- 229960001722 verapamil Drugs 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/16—Amides, e.g. hydroxamic acids
- A61K31/165—Amides, e.g. hydroxamic acids having aromatic rings, e.g. colchicine, atenolol, progabide
- A61K31/166—Amides, e.g. hydroxamic acids having aromatic rings, e.g. colchicine, atenolol, progabide having the carbon of a carboxamide group directly attached to the aromatic ring, e.g. procainamide, procarbazine, metoclopramide, labetalol
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/16—Amides, e.g. hydroxamic acids
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/16—Amides, e.g. hydroxamic acids
- A61K31/165—Amides, e.g. hydroxamic acids having aromatic rings, e.g. colchicine, atenolol, progabide
-
- 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
- A61P25/18—Antipsychotics, i.e. neuroleptics; Drugs for mania or schizophrenia
Landscapes
- Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Medicinal Chemistry (AREA)
- Epidemiology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- General Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Neurosurgery (AREA)
- Neurology (AREA)
- Biomedical Technology (AREA)
- Psychiatry (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US16181799P | 1999-10-27 | 1999-10-27 | |
| US161817P | 1999-10-27 | ||
| PCT/US2000/029618 WO2001030339A1 (en) | 1999-10-27 | 2000-10-27 | Use of 1-aminoindan derivatives for treatment of mania in bipolar mood disorder |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE60029131D1 DE60029131D1 (de) | 2006-08-10 |
| DE60029131T2 true DE60029131T2 (de) | 2007-01-18 |
Family
ID=22582876
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE60029131T Expired - Lifetime DE60029131T2 (de) | 1999-10-27 | 2000-10-27 | Verwendung von 1-aminoindanderivaten zur behandlung der manie in verbindung mit manisch-depressiver erkrankung |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US6492426B1 (enExample) |
| EP (1) | EP1242066B1 (enExample) |
| JP (1) | JP2003512426A (enExample) |
| AT (1) | ATE331508T1 (enExample) |
| AU (1) | AU775885B2 (enExample) |
| CA (1) | CA2387394C (enExample) |
| DE (1) | DE60029131T2 (enExample) |
| IL (2) | IL149308A0 (enExample) |
| WO (1) | WO2001030339A1 (enExample) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR20140090996A (ko) * | 2011-10-10 | 2014-07-18 | 테바 파마슈티컬 인더스트리즈 리미티드 | R(+)-n-폼일-프로파길-아미노인단 |
| US9181026B2 (en) | 2013-10-03 | 2015-11-10 | Custom Chemical Solutions, LLC | Containment berm with internal “L” braces |
| WO2024196698A2 (en) * | 2023-03-17 | 2024-09-26 | Curadh Mtr | Compounds and constructs useful for targeting fibroblast activation protein |
Family Cites Families (28)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB852735A (en) | 1956-04-13 | 1960-11-02 | Schering Ag | Manufacture of 1-aminoindanes |
| US3637740A (en) * | 1969-04-21 | 1972-01-25 | Pfizer | Aminobenzocycloalkane compounds |
| BE786748A (fr) * | 1971-07-26 | 1973-01-26 | Basf Ag | 1-aminomethyl-indanes-n-substitues |
| US4096173A (en) * | 1977-03-28 | 1978-06-20 | Eli Lilly And Company | Chlorinated 1-aminoindane N-methyl transferase inhibitors |
| JPS5824433A (ja) * | 1981-08-06 | 1983-02-14 | Takehiro Mokuzai Kogyo Kk | 繊維材成型品の表面化粧方法 |
| SE464194B (sv) | 1983-03-04 | 1991-03-18 | Otsuka Pharma Co Ltd | Indanderivat, foerfarande foer framstaellning daerav samt farmaceutiska kompositioner |
| EP0173331B1 (en) | 1984-08-31 | 1991-08-14 | Otsuka Pharmaceutical Co., Ltd. | 2,3-dihydro-1h-indene derivatives, a process for preparing them and pharmaceutical compositions containing same |
| US5242919A (en) | 1984-08-31 | 1993-09-07 | Otsuka Pharmaceutical Co., Ltd. | 2,3-dihydro-1H-indene derivatives |
| JPS6169747A (ja) | 1984-08-31 | 1986-04-10 | Otsuka Pharmaceut Co Ltd | ２，３―ジヒドロ―１ｈ―インデン誘導体及びその製造法 |
| US4882339A (en) | 1987-07-10 | 1989-11-21 | Ciba-Geigy Corporation | 4-Amino-substituted 1,2-dihydroxynaphthalene derivatives useful in inhibiting 5-lipoxygenase activity in mammals |
| US5744500A (en) | 1990-01-03 | 1998-04-28 | Teva Pharmaceutical Industries, Ltd. | Use of R-enantiomer of N-propargyl-1-aminoindan, salts, and compositions thereof |
| IL92952A (en) | 1990-01-03 | 1994-06-24 | Teva Pharma | R-enantiomers of n-propargyl-1-aminoindan compounds, their preparation and pharmaceutical compositions containing them |
| IL99759A (en) | 1991-10-16 | 1997-06-10 | Teva Pharma | Mono-fluorinated derivatives of n-propargyl-1-aminoindan, their preparation and pharmaceutical compositions containing them |
| US5344836A (en) | 1991-11-11 | 1994-09-06 | Ono Pharmaceutical Co., Ltd. | Fused benzeneoxyacetic acid derivatives |
| CH683996A5 (fr) | 1992-03-05 | 1994-06-30 | Symphar Sa | Dérivés aminophosphonates substitués, leur procédé de préparation et compositions pharmaceutiques les contenant. |
| KR100238346B1 (ko) | 1993-04-07 | 2000-03-02 | 오쓰까 아끼히꼬 | 피페리딘 유도체를 유효성분으로 하는 말초혈관확장제 |
| IL111240A (en) | 1993-10-18 | 2001-10-31 | Teva Pharma | Salts of r(+) - enantiomers of n- propargyl-1-aminoindan and pharmaceutical compositions comprising them |
| AU1867095A (en) | 1994-01-10 | 1995-08-01 | Technion Research & Development Foundation Ltd. | 1-aminoindan derivatives and compositions thereof |
| US5877218A (en) | 1994-01-10 | 1999-03-02 | Teva Pharmaceutical Industries, Ltd. | Compositions containing and methods of using 1-aminoindan and derivatives thereof and process for preparing optically active 1-aminoindan derivatives |
| CH690264A5 (fr) | 1995-06-30 | 2000-06-30 | Symphar Sa | Dérivés aminophosphonates substitués, leur procédé de préparation et leur utilisation pour la préparation de compositions pharmaceutiques. |
| US5646188A (en) | 1995-07-05 | 1997-07-08 | Teva Pharmaceutical Industries, Ltd. | Polyamine derivatives of 1-aminoindan |
| IL115357A (en) | 1995-09-20 | 2000-01-31 | Teva Pharma | Stable compositions containing N-propargyl-1-aminoindan and polyhydric alcohols |
| US5887218A (en) | 1996-06-10 | 1999-03-23 | Ricoh Co., Ltd. | Color image forming apparatus having toner and transfer sheet bearing members and image forming method thereof |
| DE69732984T2 (de) | 1996-12-18 | 2006-02-16 | Teva Pharmaceutical Industries Ltd. | Aminoindanderivate |
| US6251938B1 (en) | 1996-12-18 | 2001-06-26 | Teva Pharmaceutical Industries, Ltd., | Phenylethylamine derivatives |
| WO1998055447A1 (en) | 1997-06-05 | 1998-12-10 | Venantius Limited | 3-aminoindane derivatives, process for their preparation and pharmaceutical compositions containing them |
| US5887221A (en) | 1997-10-20 | 1999-03-23 | Xerox Corporation | Signature sensing for optimum toner control with donor roll |
| US6227886B1 (en) | 1999-04-16 | 2001-05-08 | Avaya Technology Corp. | Snag-resistant patchcord plug latch and cover |
-
2000
- 2000-10-27 EP EP00976661A patent/EP1242066B1/en not_active Expired - Lifetime
- 2000-10-27 AT AT00976661T patent/ATE331508T1/de not_active IP Right Cessation
- 2000-10-27 CA CA002387394A patent/CA2387394C/en not_active Expired - Fee Related
- 2000-10-27 JP JP2001532759A patent/JP2003512426A/ja active Pending
- 2000-10-27 IL IL14930800A patent/IL149308A0/xx active IP Right Grant
- 2000-10-27 AU AU14402/01A patent/AU775885B2/en not_active Ceased
- 2000-10-27 DE DE60029131T patent/DE60029131T2/de not_active Expired - Lifetime
- 2000-10-27 US US09/699,127 patent/US6492426B1/en not_active Expired - Fee Related
- 2000-10-27 WO PCT/US2000/029618 patent/WO2001030339A1/en not_active Ceased
-
2002
- 2002-04-23 IL IL149308A patent/IL149308A/en not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| JP2003512426A (ja) | 2003-04-02 |
| EP1242066A4 (en) | 2004-09-01 |
| CA2387394A1 (en) | 2001-05-03 |
| AU1440201A (en) | 2001-05-08 |
| IL149308A0 (en) | 2002-11-10 |
| EP1242066B1 (en) | 2006-06-28 |
| WO2001030339A1 (en) | 2001-05-03 |
| CA2387394C (en) | 2009-08-18 |
| IL149308A (en) | 2007-07-24 |
| DE60029131D1 (de) | 2006-08-10 |
| US6492426B1 (en) | 2002-12-10 |
| ATE331508T1 (de) | 2006-07-15 |
| EP1242066A1 (en) | 2002-09-25 |
| AU775885B2 (en) | 2004-08-19 |
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