DE10360792A1 - Spirocyclische Cyclohexan-Derivate - Google Patents
Spirocyclische Cyclohexan-Derivate Download PDFInfo
- Publication number
- DE10360792A1 DE10360792A1 DE10360792A DE10360792A DE10360792A1 DE 10360792 A1 DE10360792 A1 DE 10360792A1 DE 10360792 A DE10360792 A DE 10360792A DE 10360792 A DE10360792 A DE 10360792A DE 10360792 A1 DE10360792 A1 DE 10360792A1
- Authority
- DE
- Germany
- Prior art keywords
- unsubstituted
- polysubstituted
- alkyl
- monosubstituted
- heteroaryl
- 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.)
- Withdrawn
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- 125000000113 cyclohexyl group Chemical class [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 title claims abstract description 24
- 239000003814 drug Substances 0.000 claims abstract description 22
- 238000002360 preparation method Methods 0.000 claims abstract description 12
- 238000000034 method Methods 0.000 claims abstract description 8
- 230000008569 process Effects 0.000 claims abstract description 7
- 125000001072 heteroaryl group Chemical group 0.000 claims description 51
- 125000003118 aryl group Chemical group 0.000 claims description 49
- 229920006395 saturated elastomer Polymers 0.000 claims description 44
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 35
- 125000000217 alkyl group Chemical group 0.000 claims description 35
- 150000003839 salts Chemical class 0.000 claims description 28
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 26
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 22
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 19
- RGSFGYAAUTVSQA-UHFFFAOYSA-N pentamethylene Natural products C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 claims description 19
- 125000004817 pentamethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 claims description 19
- 239000002253 acid Substances 0.000 claims description 16
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 15
- 208000002193 Pain Diseases 0.000 claims description 14
- 229910052739 hydrogen Inorganic materials 0.000 claims description 13
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 11
- 150000001768 cations Chemical class 0.000 claims description 11
- 150000007513 acids Chemical class 0.000 claims description 10
- 239000000203 mixture Substances 0.000 claims description 10
- 125000000896 monocarboxylic acid group Chemical group 0.000 claims description 10
- 229910052717 sulfur Inorganic materials 0.000 claims description 10
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 9
- 229910052799 carbon Inorganic materials 0.000 claims description 9
- 229910052760 oxygen Inorganic materials 0.000 claims description 9
- 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 claims description 8
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims description 8
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- 238000004519 manufacturing process Methods 0.000 claims description 8
- 239000004480 active ingredient Substances 0.000 claims description 7
- 230000036407 pain Effects 0.000 claims description 7
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 6
- 125000001544 thienyl group Chemical group 0.000 claims description 6
- 208000007271 Substance Withdrawal Syndrome Diseases 0.000 claims description 5
- 230000003444 anaesthetic effect Effects 0.000 claims description 5
- 229940005483 opioid analgesics Drugs 0.000 claims description 5
- 125000004076 pyridyl group Chemical group 0.000 claims description 5
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- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 4
- 208000000094 Chronic Pain Diseases 0.000 claims description 4
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims description 4
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 claims description 4
- 229940098779 methanesulfonic acid Drugs 0.000 claims description 4
- 208000004296 neuralgia Diseases 0.000 claims description 4
- 208000021722 neuropathic pain Diseases 0.000 claims description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 4
- 208000011117 substance-related disease Diseases 0.000 claims description 4
- 206010012735 Diarrhoea Diseases 0.000 claims description 3
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- 239000000654 additive Substances 0.000 claims description 3
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- 230000037406 food intake Effects 0.000 claims description 3
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- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
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- 230000003957 neurotransmitter release Effects 0.000 claims description 3
- 230000001777 nootropic effect Effects 0.000 claims description 3
- 125000006239 protecting group Chemical group 0.000 claims description 3
- 230000009467 reduction Effects 0.000 claims description 3
- 239000002904 solvent Substances 0.000 claims description 3
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 2
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 claims description 2
- 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 claims description 2
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- 206010039966 Senile dementia Diseases 0.000 claims description 2
- 201000001880 Sexual dysfunction Diseases 0.000 claims description 2
- 208000009205 Tinnitus Diseases 0.000 claims description 2
- 125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 claims description 2
- 229910000147 aluminium phosphate Inorganic materials 0.000 claims description 2
- 150000008064 anhydrides Chemical class 0.000 claims description 2
- 208000022531 anorexia Diseases 0.000 claims description 2
- 230000001773 anti-convulsant effect Effects 0.000 claims description 2
- 239000001961 anticonvulsive agent Substances 0.000 claims description 2
- 229960003965 antiepileptics Drugs 0.000 claims description 2
- 230000036506 anxiety Effects 0.000 claims description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 2
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- 230000003137 locomotive effect Effects 0.000 claims description 2
- 206010027599 migraine Diseases 0.000 claims description 2
- 239000003158 myorelaxant agent Substances 0.000 claims description 2
- LYGJENNIWJXYER-UHFFFAOYSA-N nitromethane Chemical compound C[N+]([O-])=O LYGJENNIWJXYER-UHFFFAOYSA-N 0.000 claims description 2
- 235000020824 obesity Nutrition 0.000 claims description 2
- 239000000014 opioid analgesic Substances 0.000 claims description 2
- 239000007800 oxidant agent Substances 0.000 claims description 2
- 231100000872 sexual dysfunction Toxicity 0.000 claims description 2
- 208000011580 syndromic disease Diseases 0.000 claims description 2
- 231100000886 tinnitus Toxicity 0.000 claims description 2
- 150000004677 hydrates Chemical class 0.000 claims 2
- 239000012453 solvate Substances 0.000 claims 2
- ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical compound OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-N 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 abstract description 17
- 239000008194 pharmaceutical composition Substances 0.000 abstract 1
- 150000001934 cyclohexanes Chemical class 0.000 description 27
- -1 2-hexyl Chemical group 0.000 description 17
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 15
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- 108010020615 nociceptin receptor Proteins 0.000 description 12
- 150000003254 radicals Chemical class 0.000 description 12
- 239000007787 solid Substances 0.000 description 11
- 108090000622 Nociceptin Proteins 0.000 description 9
- 102000048266 Nociceptin Human genes 0.000 description 8
- 125000002877 alkyl aryl group Chemical group 0.000 description 8
- PULGYDLMFSFVBL-SMFNREODSA-N nociceptin Chemical compound C([C@@H](C(=O)N[C@H](C(=O)NCC(=O)N[C@@H](C)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CO)C(=O)N[C@@H](C)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](C)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H](CCC(N)=O)C(O)=O)[C@@H](C)O)NC(=O)CNC(=O)CNC(=O)[C@@H](N)CC=1C=CC=CC=1)C1=CC=CC=C1 PULGYDLMFSFVBL-SMFNREODSA-N 0.000 description 8
- 125000001424 substituent group Chemical group 0.000 description 7
- KRKNYBCHXYNGOX-UHFFFAOYSA-K Citrate Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 description 6
- 150000001450 anions Chemical class 0.000 description 6
- 239000000243 solution Substances 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
- 241000124008 Mammalia Species 0.000 description 5
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 5
- 239000002585 base Substances 0.000 description 5
- 125000004432 carbon atom Chemical group C* 0.000 description 5
- 125000005842 heteroatom Chemical group 0.000 description 5
- 238000006467 substitution reaction Methods 0.000 description 5
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- QIAFMBKCNZACKA-UHFFFAOYSA-N Hippuric acid Natural products OC(=O)CNC(=O)C1=CC=CC=C1 QIAFMBKCNZACKA-UHFFFAOYSA-N 0.000 description 4
- PVNIIMVLHYAWGP-UHFFFAOYSA-N Niacin Chemical compound OC(=O)C1=CC=CN=C1 PVNIIMVLHYAWGP-UHFFFAOYSA-N 0.000 description 4
- 108090000137 Opioid Receptors Proteins 0.000 description 4
- 102000003840 Opioid Receptors Human genes 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
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- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 4
- 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 4
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- LUTOSMMOQSDXDA-UHFFFAOYSA-N 4-(dimethylamino)-4-pyridin-2-ylcyclohexan-1-one Chemical compound C=1C=CC=NC=1C1(N(C)C)CCC(=O)CC1 LUTOSMMOQSDXDA-UHFFFAOYSA-N 0.000 description 3
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- C—CHEMISTRY; METALLURGY
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- 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
- C07D491/02—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 two hetero rings
- C07D491/10—Spiro-condensed systems
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
- C07D495/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D495/10—Spiro-condensed systems
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Priority Applications (29)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE10360792A DE10360792A1 (de) | 2003-12-23 | 2003-12-23 | Spirocyclische Cyclohexan-Derivate |
| RU2006126787/04A RU2383544C2 (ru) | 2003-12-23 | 2004-12-21 | Спироциклические производные циклогексана со сродством к orl1-рецептору |
| HR20080272T HRP20080272T3 (en) | 2003-12-23 | 2004-12-21 | Spirocyclic cyclohexane derivatives with affinity to the orl-1 receptor |
| SI200430663T SI1725567T1 (sl) | 2003-12-23 | 2004-12-21 | Spirociklični cikloheksanski derivati z afiniteto za ORL1 receptor |
| DE502004006697T DE502004006697D1 (de) | 2003-12-23 | 2004-12-21 | Spirocyclische cyclohexan-derivate mit affinität zum orl1-rezeptor |
| PT04804136T PT1725567E (pt) | 2003-12-23 | 2004-12-21 | Derivados espirocíclicos de ciclo-hexano com afinidade para o receptor orl-1 |
| HK07103179.0A HK1095831B (en) | 2003-12-23 | 2004-12-21 | Spirocyclic cyclohexane derivatives with affinity to the orl-1 receptor |
| PL04804136T PL1725567T3 (pl) | 2003-12-23 | 2004-12-21 | Spirocykliczne pochodne cykloheksanu o powinowactwie do receptora-ORL1 |
| EP04804136A EP1725567B1 (de) | 2003-12-23 | 2004-12-21 | Spirocyclische cyclohexan-derivate mit affinität zum orl1-rezeptor |
| KR1020067014815A KR101152693B1 (ko) | 2003-12-23 | 2004-12-21 | Ｏｒｌ1 수용체에 대해 친화력을 가진 스피로사이클사이클로헥산 유도체 |
| AT04804136T ATE390430T1 (de) | 2003-12-23 | 2004-12-21 | Spirocyclische cyclohexan-derivate mit affinität zum orl1-rezeptor |
| NZ548317A NZ548317A (en) | 2003-12-23 | 2004-12-21 | Spirocyclic cyclohexane derivatives with affinity for the ORL1-receptor |
| BRPI0418052A BRPI0418052A2 (pt) | 2003-12-23 | 2004-12-21 | derivados de ciclohexano espiro-cíclicos com afinidade para o receptor orl1 |
| AU2004312147A AU2004312147B2 (en) | 2003-12-23 | 2004-12-21 | Spirocyclic cyclohexane derivatives with affinity for the ORL1-receptor |
| CN2004800420360A CN1922189B (zh) | 2003-12-23 | 2004-12-21 | 对orl1受体具有亲合力的螺环环己烷衍生物 |
| PCT/EP2004/014539 WO2005066183A1 (de) | 2003-12-23 | 2004-12-21 | Spirocyclische cyclohexan-derivate mit affinität zum orl1-rezeptor |
| CA2550868A CA2550868C (en) | 2003-12-23 | 2004-12-21 | Spirocyclic cyclohexane derivatives with affinity for the orl1-receptor |
| JP2006546040A JP4885733B2 (ja) | 2003-12-23 | 2004-12-21 | Ｏｒｌ１レセプターに対する親和性を有するスピロ環状シクロヘキサン誘導体 |
| ES04804136T ES2303964T3 (es) | 2003-12-23 | 2004-12-21 | Derivados de ciclohexano espirociclicos con afinidad por el receptor orl1. |
| MXPA06007171A MXPA06007171A (es) | 2003-12-23 | 2004-12-21 | Derivados de ciclohexano espirociclicos con afinidad para el receptor orl1. |
| DK04804136T DK1725567T3 (da) | 2003-12-23 | 2004-12-21 | Spirocykliske cyclohexanderivater med affinitet for ORL1-receptoren |
| ARP040104857A AR047163A1 (es) | 2003-12-23 | 2004-12-22 | Derivados de ciclohexano espirociclicos con afinidad por el receptor orl1 |
| US11/019,372 US7332519B2 (en) | 2003-12-23 | 2004-12-23 | Spirocyclic cyclohexane compounds |
| PE2005000023A PE20050758A1 (es) | 2003-12-23 | 2005-01-03 | Derivados de ciclohexano espirociclicos |
| IL176457A IL176457A (en) | 2003-12-23 | 2006-06-21 | Cyclohexane Spiro History Compressed with Ortho-Compressed Tricyclic System, Process for Preparation and Pharmaceuticals Containing Them |
| EC2006006667A ECSP066667A (es) | 2003-12-23 | 2006-06-21 | Derivados de ciclohexano espirociclicos |
| ZA200606067A ZA200606067B (en) | 2003-12-23 | 2006-07-21 | Spirocyclic cyclohexane derivatives with affinity for the ORL 1-receptor |
| NO20063422A NO337127B1 (no) | 2003-12-23 | 2006-07-24 | Spirosykliske sykloheksanderivater, fremgangsmåter for deres fremstilling, legemidler inneholdende derivatene samt anvendelse av derivatene for fremstilling av legemidler |
| CY20081100557T CY1107975T1 (el) | 2003-12-23 | 2008-05-29 | Σπειροκυκλικα παραγωγα κυκλοεξανιου με χημικη συγγενεια προς τον υποδοχεα orl1 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE10360792A DE10360792A1 (de) | 2003-12-23 | 2003-12-23 | Spirocyclische Cyclohexan-Derivate |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE10360792A1 true DE10360792A1 (de) | 2005-07-28 |
Family
ID=34706497
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE10360792A Withdrawn DE10360792A1 (de) | 2003-12-23 | 2003-12-23 | Spirocyclische Cyclohexan-Derivate |
| DE502004006697T Expired - Lifetime DE502004006697D1 (de) | 2003-12-23 | 2004-12-21 | Spirocyclische cyclohexan-derivate mit affinität zum orl1-rezeptor |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE502004006697T Expired - Lifetime DE502004006697D1 (de) | 2003-12-23 | 2004-12-21 | Spirocyclische cyclohexan-derivate mit affinität zum orl1-rezeptor |
Country Status (27)
| Country | Link |
|---|---|
| US (1) | US7332519B2 (enExample) |
| EP (1) | EP1725567B1 (enExample) |
| JP (1) | JP4885733B2 (enExample) |
| KR (1) | KR101152693B1 (enExample) |
| CN (1) | CN1922189B (enExample) |
| AR (1) | AR047163A1 (enExample) |
| AT (1) | ATE390430T1 (enExample) |
| AU (1) | AU2004312147B2 (enExample) |
| BR (1) | BRPI0418052A2 (enExample) |
| CA (1) | CA2550868C (enExample) |
| CY (1) | CY1107975T1 (enExample) |
| DE (2) | DE10360792A1 (enExample) |
| DK (1) | DK1725567T3 (enExample) |
| EC (1) | ECSP066667A (enExample) |
| ES (1) | ES2303964T3 (enExample) |
| HR (1) | HRP20080272T3 (enExample) |
| IL (1) | IL176457A (enExample) |
| MX (1) | MXPA06007171A (enExample) |
| NO (1) | NO337127B1 (enExample) |
| NZ (1) | NZ548317A (enExample) |
| PE (1) | PE20050758A1 (enExample) |
| PL (1) | PL1725567T3 (enExample) |
| PT (1) | PT1725567E (enExample) |
| RU (1) | RU2383544C2 (enExample) |
| SI (1) | SI1725567T1 (enExample) |
| WO (1) | WO2005066183A1 (enExample) |
| ZA (1) | ZA200606067B (enExample) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE102006019597A1 (de) * | 2006-04-27 | 2007-10-31 | Grünenthal GmbH | Spirocyclische Cyclohexan-Derivate |
| DE102007009319A1 (de) * | 2007-02-22 | 2008-08-28 | Grünenthal GmbH | Spirocyclische Cyclohexan-Derivate |
| DE102007009235A1 (de) * | 2007-02-22 | 2008-09-18 | Grünenthal GmbH | Spirocyclische Cyclohexan-Derivate |
Families Citing this family (73)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7776314B2 (en) | 2002-06-17 | 2010-08-17 | Grunenthal Gmbh | Abuse-proofed dosage system |
| DE10252667A1 (de) * | 2002-11-11 | 2004-05-27 | Grünenthal GmbH | Spirocyclische Cyclohexan-Derivate |
| DE10361596A1 (de) | 2003-12-24 | 2005-09-29 | Grünenthal GmbH | Verfahren zur Herstellung einer gegen Missbrauch gesicherten Darreichungsform |
| DE102005005446A1 (de) | 2005-02-04 | 2006-08-10 | Grünenthal GmbH | Bruchfeste Darreichungsformen mit retardierter Freisetzung |
| US8075872B2 (en) | 2003-08-06 | 2011-12-13 | Gruenenthal Gmbh | Abuse-proofed dosage form |
| US20070048228A1 (en) | 2003-08-06 | 2007-03-01 | Elisabeth Arkenau-Maric | Abuse-proofed dosage form |
| DE102004032051A1 (de) | 2004-07-01 | 2006-01-19 | Grünenthal GmbH | Verfahren zur Herstellung einer gegen Missbrauch gesicherten, festen Darreichungsform |
| DE10336400A1 (de) | 2003-08-06 | 2005-03-24 | Grünenthal GmbH | Gegen Missbrauch gesicherte Darreichungsform |
| DE10360793A1 (de) * | 2003-12-23 | 2005-07-28 | Grünenthal GmbH | Spirocyclische Cyclohexan-Derivate |
| DE102004032049A1 (de) | 2004-07-01 | 2006-01-19 | Grünenthal GmbH | Gegen Missbrauch gesicherte, orale Darreichungsform |
| DE102005005449A1 (de) | 2005-02-04 | 2006-08-10 | Grünenthal GmbH | Verfahren zur Herstellung einer gegen Missbrauch gesicherten Darreichungsform |
| DE102005016460A1 (de) | 2005-04-11 | 2006-10-19 | Grünenthal GmbH | Spriocyclische Cyclohexanderivate zur Behandlung von Substanzabhängigkeit |
| DE102006033114A1 (de) * | 2006-07-18 | 2008-01-24 | Grünenthal GmbH | Spirocyclische Azaindol-Derivate |
| EP1894938A1 (en) * | 2006-08-31 | 2008-03-05 | Evonik Degussa GmbH | New cyclopentadienyl, indenyl or fluorenyl substituted phosphine compounds and their use in catalytic reactions |
| DE102006046745A1 (de) * | 2006-09-29 | 2008-04-03 | Grünenthal GmbH | Gemischte ORL1/µ-Agonisten zur Behandlung von Schmerz |
| DE102007011485A1 (de) | 2007-03-07 | 2008-09-11 | Grünenthal GmbH | Darreichungsform mit erschwertem Missbrauch |
| KR101614723B1 (ko) | 2008-01-11 | 2016-04-22 | 알바니 몰레큘라 리써치, 인크. | Ｍｃｈ 길항물질로서 (1-아지논)-치환된 피리도인돌 |
| NZ586792A (en) | 2008-01-25 | 2012-09-28 | Gruenenthal Chemie | Tamper resistant controlled release pharmaceutical tablets form having convex and concave surfaces |
| AU2009228643B2 (en) * | 2008-03-27 | 2013-07-11 | Grunenthal Gmbh | Spiro(5.5)undecane derivatives |
| CN103183630A (zh) | 2008-03-27 | 2013-07-03 | 格吕伦塔尔有限公司 | 取代的4-氨基环己烷衍生物 |
| PL2271613T3 (pl) | 2008-03-27 | 2014-09-30 | Gruenenthal Gmbh | Hydroksymetylocykloheksyloaminy |
| JP5597188B2 (ja) * | 2008-03-27 | 2014-10-01 | グリュネンタール・ゲゼルシャフト・ミト・ベシュレンクテル・ハフツング | 置換されたスピロ環状シクロヘキサン誘導体 |
| US8357705B2 (en) | 2008-03-27 | 2013-01-22 | Gruenenthal Gmbh | Substituted cyclohexyldiamines |
| WO2009118163A1 (de) | 2008-03-27 | 2009-10-01 | Grünenthal GmbH | (hetero-)aryl-cyclohexan-derivate |
| RU2508092C2 (ru) | 2008-05-09 | 2014-02-27 | Грюненталь Гмбх | Способ получения твердой лекарственной формы, в частности таблетки для фармацевтического применения, и способ получения прекурсора твердой лекарственной формы, в частности таблетки |
| PE20110537A1 (es) | 2008-11-13 | 2011-08-04 | Hoffmann La Roche | ESPIRO-5,6-DIHIDRO-4H-2,3,5,10B-TETRAAZA-BENZO[E]AZULENOS COMO ANTAGONISTAS DE LA V1a |
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| US8618299B2 (en) * | 2009-07-01 | 2013-12-31 | Albany Molecular Research, Inc. | Azinone-substituted azapolycycle MCH-1 antagonists, methods of making, and use thereof |
| WO2011003021A1 (en) * | 2009-07-01 | 2011-01-06 | Albany Molecular Research, Inc. | Azinone-substituted azabicycloalkane-indole and azabicycloalkane-pyrrolo-pyridine mch-1 antagonists, methods of making, and use thereof |
| JP2012532144A (ja) * | 2009-07-01 | 2012-12-13 | アルバニー モレキュラー リサーチ， インコーポレイテッド | アジノン置換アゼピノ［ｂ］インドールおよびピリド−ピロロ−アゼピンｍｃｈ−１拮抗薬、ならびにその作製方法および使用 |
| ES2534908T3 (es) | 2009-07-22 | 2015-04-30 | Grünenthal GmbH | Forma de dosificación de liberación controlada extruida por fusión en caliente |
| PL2456424T3 (pl) | 2009-07-22 | 2013-12-31 | Gruenenthal Gmbh | Stabilizowana przed utlenianiem odporna na naruszenie postać dawkowania |
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| UA107943C2 (xx) | 2009-11-16 | 2015-03-10 | Lilly Co Eli | Сполуки спіропіперидину як антагоністи рецептора orl-1 |
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| PL2611425T3 (pl) | 2010-09-02 | 2014-09-30 | Gruenenthal Gmbh | Odporna na ingerencję postać dawki zawierająca polimer anionowy |
| AR082861A1 (es) | 2010-09-02 | 2013-01-16 | Gruenenthal Gmbh | Forma de dosificacion resistente a alteracion que comprende un polimero anionico |
| PE20131102A1 (es) | 2010-09-02 | 2013-10-12 | Gruenenthal Chemie | Forma de dosificacion resistente a manipulacion que comprende una sal inorganica |
| US8993765B2 (en) | 2010-12-21 | 2015-03-31 | Albany Molecular Research, Inc. | Tetrahydro-azacarboline MCH-1 antagonists, methods of making, and uses thereof |
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| CA2839123A1 (en) | 2011-07-29 | 2013-02-07 | Grunenthal Gmbh | Tamper-resistant tablet providing immediate drug release |
| NO2736497T3 (enExample) | 2011-07-29 | 2018-01-20 | ||
| EA025500B1 (ru) * | 2012-02-03 | 2016-12-30 | Грюненталь Гмбх | (1R,4R)-6'-ФТОР-(N-МЕТИЛ- ИЛИ N,N-ДИМЕТИЛ-)-4-ФЕНИЛ-4',9'-ДИГИДРО-3'Н-СПИРО[ЦИКЛОГЕКСАН-1,1'-ПИРАНО[3,4,b]ИНДОЛ]-4-АМИН ДЛЯ ЛЕЧЕНИЯ ФИБРОМИАЛГИИ И СИНДРОМА ХРОНИЧЕСКОЙ УСТАЛОСТИ |
| WO2013127831A1 (en) | 2012-02-28 | 2013-09-06 | Grünenthal GmbH | Tamper-resistant dosage form comprising pharmacologically active compound and anionic polymer |
| EP2819657A1 (en) | 2012-02-28 | 2015-01-07 | Grünenthal GmbH | Tamper-resistant pharmaceutical dosage form comprising nonionic surfactant |
| DK2838512T3 (en) | 2012-04-18 | 2018-11-19 | Gruenenthal Gmbh | MANIPULATED AND DOSAGE DUMPED PHARMACEUTICAL DOSAGE FORM |
| MX357783B (es) | 2012-05-11 | 2018-07-25 | Gruenenthal Gmbh | Forma de dosificacion farmaceutica termoconformada, resistente al uso indebido, que contiene zinc. |
| US10064945B2 (en) | 2012-05-11 | 2018-09-04 | Gruenenthal Gmbh | Thermoformed, tamper-resistant pharmaceutical dosage form containing zinc |
| US9320729B2 (en) * | 2012-05-18 | 2016-04-26 | Gruenenthal Gmbh | Pharmaceutical composition comprising (1r,4r)-6′-flouro-N,N-dimethyl-4-phenyl-4′,9′-dihydro-3′H-spiro[cyclohexane-1,1′-pyrano-[3,4,b]indol]-4-amine and a propionic acid derivative |
| US8912226B2 (en) * | 2012-05-18 | 2014-12-16 | Gruenenthal Gmbh | Pharmaceutical composition comprising (1r,4r) -6′-fluoro-N,N-dimethyl-4-phenyl-4′,9′-dihydro-3′H-spiro[cyclohexane-1,1′-pyrano[3,4,b]indol]-4-amine and a NSAR |
| US9308196B2 (en) | 2012-05-18 | 2016-04-12 | Gruenenthal Gmbh | Pharmaceutical composition comprising (1 r,4r) -6'-fluoro-N ,N-dimethyl-4-phenyl-4',9'-d ihydro-3'H-spiro[cyclohexane-1,1'-pyrano-[3,4,b]indol]-4-amine and an oxicam |
| US20130310385A1 (en) * | 2012-05-18 | 2013-11-21 | Gruenenthal Gmbh | Pharmaceutical Composition Comprising (1r,4r)-6'-fluoro-N,N-dimethyl-4-phenyl-4',9'-dihydro-3'H-spiro[cyclohexane-1,1'-pyrano[3,4,b]indol]-4-amine and Antidepressants |
| US9320725B2 (en) * | 2012-05-18 | 2016-04-26 | Gruenenthal Gmbh | Pharmaceutical composition comprising (1r,4r)-6′-fluoro-N,N-dimethyl-4-phenyl-4′9′-dihydro-3′H-spiro[cyclohexane-1,1′-pyrano[3,4,b]indol]-4-amine and a gabapentinoid |
| US9345689B2 (en) * | 2012-05-18 | 2016-05-24 | Gruenenthal Gmbh | Pharmaceutical composition comprising (1r,4r)-6′-fluoro-N, N-dimethyl-4-phenyl-4,9′-dihydro-3′H-spiro[cyclohexane-1,1′-pyrano[3,4,b]indol]-4-amine and an anticonvulsant |
| US20130310435A1 (en) | 2012-05-18 | 2013-11-21 | Gruenenthal Gmbh | Pharmaceutical Composition Comprising (1r,4r)-6'-fluoro-N, N-dimethyl-4-phenyl-4,9' -dihydro-3'H-spiro[cyclohexane-1,1' -pyrano[3,4,b]indol]-4-amine and Paracetamol or Propacetamol |
| US9855286B2 (en) | 2012-05-18 | 2018-01-02 | Gruenenthal Gmbh | Pharmaceutical composition comprising (1r,4r)-6′-fluoro-N,N-di methyl-4-phenyl-4′,9′-dihydro-3′H-spiro[cyclohexane-1,1′-pyrano-[3,4,b]indol]-4-amine and a salicylic acid component |
| SI2970284T1 (en) | 2013-03-15 | 2018-02-28 | Gruenenthal Gmbh | Crystalline cis- (E) -4- (3-fluorophenyl) -2 ', 3', 4 ', 9'-tetrahydro-N, N-dimethyl-2' - (1-oxo-3-phenyl-2-propenyl ) -spiro (cyclohexane-1,1 '(1H) -pyrido (3,4-b) indol) -4-amine |
| JP6466417B2 (ja) | 2013-05-29 | 2019-02-06 | グリュネンタール・ゲゼルシャフト・ミト・ベシュレンクテル・ハフツング | 二峰性放出プロファイルを有する改変防止（ｔａｍｐｅｒ−ｒｅｓｉｓｔａｎｔ）剤形 |
| AU2014273227B2 (en) | 2013-05-29 | 2019-08-15 | Grunenthal Gmbh | Tamper-resistant dosage form containing one or more particles |
| BR112016000194A8 (pt) | 2013-07-12 | 2019-12-31 | Gruenenthal Gmbh | forma de dosagem resistente à violação contendo o polímero de acetato de etileno-vinila |
| WO2015078891A1 (en) | 2013-11-26 | 2015-06-04 | Farmaceutici Formenti S.P.A. | Preparation of a powdery pharmaceutical composition by means of cryo-milling |
| WO2015091352A1 (en) | 2013-12-16 | 2015-06-25 | Grünenthal GmbH | Tamper resistant dosage form with bimodal release profile manufactured by co-extrusion |
| CN106572980A (zh) | 2014-05-12 | 2017-04-19 | 格吕伦塔尔有限公司 | 包含他喷他多的防篡改即释胶囊制剂 |
| EA201692388A1 (ru) | 2014-05-26 | 2017-05-31 | Грюненталь Гмбх | Лекарственная форма в виде множества частиц, защищенная от вызываемого этанолом сброса дозы |
| DK3169666T3 (en) | 2014-07-15 | 2018-07-30 | Gruenenthal Gmbh | SUBSTITUTED AZASPIRO (4.5) DECAN DERIVATES |
| TW201607923A (zh) | 2014-07-15 | 2016-03-01 | 歌林達有限公司 | 被取代之氮螺環（４．５）癸烷衍生物 |
| CA2975653A1 (en) | 2015-02-03 | 2016-08-11 | Grunenthal Gmbh | Tamper-resistant dosage form comprising a polyethylene glycol graft copolymer |
| MX2017013637A (es) | 2015-04-24 | 2018-03-08 | Gruenenthal Gmbh | Forma de dosificacion resistente a alteraciones con liberacion inmediata y resistencia contra la extraccion por solventes. |
| CA2998259A1 (en) | 2015-09-10 | 2017-03-16 | Grunenthal Gmbh | Protecting oral overdose with abuse deterrent immediate release formulations |
| CN108474002B (zh) | 2015-10-22 | 2023-05-23 | 朱诺治疗学有限公司 | 用于转导的方法、反应剂盒、反应剂和设备 |
| CA3029869A1 (en) | 2016-07-06 | 2018-01-11 | Grunenthal Gmbh | Reinforced pharmaceutical dosage form |
| GB202306662D0 (en) | 2023-05-05 | 2023-06-21 | Union Therapeutics As | Dosage regimen |
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- 2004-12-21 EP EP04804136A patent/EP1725567B1/de not_active Expired - Lifetime
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- 2004-12-21 DE DE502004006697T patent/DE502004006697D1/de not_active Expired - Lifetime
- 2004-12-21 RU RU2006126787/04A patent/RU2383544C2/ru not_active IP Right Cessation
- 2004-12-22 AR ARP040104857A patent/AR047163A1/es not_active Application Discontinuation
- 2004-12-23 US US11/019,372 patent/US7332519B2/en not_active Expired - Fee Related
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| DE102006019597A1 (de) * | 2006-04-27 | 2007-10-31 | Grünenthal GmbH | Spirocyclische Cyclohexan-Derivate |
| DE102007009319A1 (de) * | 2007-02-22 | 2008-08-28 | Grünenthal GmbH | Spirocyclische Cyclohexan-Derivate |
| DE102007009235A1 (de) * | 2007-02-22 | 2008-09-18 | Grünenthal GmbH | Spirocyclische Cyclohexan-Derivate |
| US7960404B2 (en) | 2007-02-22 | 2011-06-14 | Gruenenthal Gmbh | Spirocyclic cyclohexane compounds |
| US8404740B2 (en) | 2007-02-22 | 2013-03-26 | Gruenenthal Gmbh | Spirocyclic cyclohexane compounds |
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