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- Withdrawn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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- 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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- 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 |
| DE502004006697T DE502004006697D1 (de) | 2003-12-23 | 2004-12-21 | Spirocyclische cyclohexan-derivate mit affinität zum orl1-rezeptor |
| ES04804136T ES2303964T3 (es) | 2003-12-23 | 2004-12-21 | Derivados de ciclohexano espirociclicos con afinidad por el receptor orl1. |
| PT04804136T PT1725567E (pt) | 2003-12-23 | 2004-12-21 | Derivados espirocíclicos de ciclo-hexano com afinidade para o receptor orl-1 |
| PL04804136T PL1725567T3 (pl) | 2003-12-23 | 2004-12-21 | Spirocykliczne pochodne cykloheksanu o powinowactwie do receptora-ORL1 |
| NZ548317A NZ548317A (en) | 2003-12-23 | 2004-12-21 | Spirocyclic cyclohexane derivatives with affinity for the ORL1-receptor |
| CA2550868A CA2550868C (en) | 2003-12-23 | 2004-12-21 | Spirocyclic cyclohexane derivatives with affinity for the orl1-receptor |
| HR20080272T HRP20080272T3 (en) | 2003-12-23 | 2004-12-21 | Spirocyclic cyclohexane derivatives with affinity to the orl-1 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 |
| SI200430663T SI1725567T1 (sl) | 2003-12-23 | 2004-12-21 | Spirociklični cikloheksanski derivati z afiniteto za ORL1 receptor |
| DK04804136T DK1725567T3 (da) | 2003-12-23 | 2004-12-21 | Spirocykliske cyclohexanderivater med affinitet for ORL1-receptoren |
| AT04804136T ATE390430T1 (de) | 2003-12-23 | 2004-12-21 | Spirocyclische cyclohexan-derivate mit affinität zum orl1-rezeptor |
| 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 |
| MXPA06007171A MXPA06007171A (es) | 2003-12-23 | 2004-12-21 | Derivados de ciclohexano espirociclicos con afinidad para el receptor orl1. |
| RU2006126787/04A RU2383544C2 (ru) | 2003-12-23 | 2004-12-21 | Спироциклические производные циклогексана со сродством к orl1-рецептору |
| 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 |
| AU2004312147A AU2004312147B2 (en) | 2003-12-23 | 2004-12-21 | Spirocyclic cyclohexane derivatives with affinity for the ORL1-receptor |
| HK07103179.0A HK1095831B (en) | 2003-12-23 | 2004-12-21 | Spirocyclic cyclohexane derivatives with affinity to the orl-1 receptor |
| PCT/EP2004/014539 WO2005066183A1 (de) | 2003-12-23 | 2004-12-21 | Spirocyclische cyclohexan-derivate mit affinität zum orl1-rezeptor |
| BRPI0418052A BRPI0418052A2 (pt) | 2003-12-23 | 2004-12-21 | derivados de ciclohexano espiro-cíclicos com afinidade para o receptor orl1 |
| 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 |
| EC2006006667A ECSP066667A (es) | 2003-12-23 | 2006-06-21 | 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 |
| 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 |
| US8075872B2 (en) | 2003-08-06 | 2011-12-13 | Gruenenthal Gmbh | Abuse-proofed dosage form |
| DE10336400A1 (de) | 2003-08-06 | 2005-03-24 | Grünenthal GmbH | Gegen Missbrauch gesicherte Darreichungsform |
| DE10361596A1 (de) | 2003-12-24 | 2005-09-29 | Grünenthal GmbH | Verfahren zur Herstellung einer gegen Missbrauch gesicherten Darreichungsform |
| 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 |
| DE102005005446A1 (de) | 2005-02-04 | 2006-08-10 | Grünenthal GmbH | Bruchfeste Darreichungsformen mit retardierter Freisetzung |
| 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 |
| EP2240481A1 (en) | 2008-01-11 | 2010-10-20 | Albany Molecular Research, Inc. | (1-azinone) -substituted pyridoindoles as mch antagonists |
| US8383152B2 (en) | 2008-01-25 | 2013-02-26 | Gruenenthal Gmbh | Pharmaceutical dosage form |
| SI2271613T1 (sl) | 2008-03-27 | 2014-08-29 | Grunenthal Gmbh | Hidroksimetilcikloheksilamini |
| US8288430B2 (en) * | 2008-03-27 | 2012-10-16 | Grunenthal Gmbh | Spiro(5.5)undecane derivatives |
| TWI450899B (zh) * | 2008-03-27 | 2014-09-01 | 被取代之螺環環已烷衍生物 | |
| CA2719743A1 (en) | 2008-03-27 | 2009-10-01 | Gruenenthal Gmbh | Substituted cyclohexyldiamines |
| AR071066A1 (es) | 2008-03-27 | 2010-05-26 | Gruenenthal Chemie | Derivados de (hetero) aril-ciclohexano |
| RU2532545C2 (ru) | 2008-03-27 | 2014-11-10 | Грюненталь Гмбх | Замещенные производные 4-аминоциклогексана |
| TWI524904B (zh) | 2008-05-09 | 2016-03-11 | 歌林達股份有限公司 | 製備醫藥用固體劑型，尤指錠劑之方法，及製備固體劑型，尤指錠劑之前驅物之方法 |
| EP2356123B1 (en) | 2008-11-13 | 2012-10-03 | F.Hoffmann-La Roche Ag | Spiro-5,6-dihydro-4h-2,3,5,10b-tetraaza-benzo[e]azulenes |
| WO2011003005A1 (en) * | 2009-07-01 | 2011-01-06 | Albany Molecular Research, Inc. | Azinone-substituted azepino[b]indole and pyrido-pyrrolo-azepine mch-1 antagonists, methods of making, and use thereof |
| WO2011003012A1 (en) * | 2009-07-01 | 2011-01-06 | 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 |
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| JP5667183B2 (ja) | 2009-07-22 | 2015-02-12 | 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 | 加熱溶融押出成型した制御放出性投与剤型 |
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| MX2012005690A (es) * | 2009-11-16 | 2012-06-13 | Lilly Co Eli | Compuestos de espiropiperidina como antagonista del receptor orl-1. |
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| US10064945B2 (en) | 2012-05-11 | 2018-09-04 | Gruenenthal Gmbh | Thermoformed, tamper-resistant pharmaceutical dosage form containing zinc |
| LT2846835T (lt) | 2012-05-11 | 2017-12-27 | Grünenthal GmbH | Termiškai suformuota, sugadinimui atspari vaistinė dozavimo forma, turinti cinko |
| 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 |
| 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 |
| 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 |
| 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 |
| 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 |
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| 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 |
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| BR112015026549A2 (pt) | 2013-05-29 | 2017-07-25 | Gruenenthal Gmbh | forma de dosagem à prova de violação contendo uma ou mais partículas |
| US9737490B2 (en) | 2013-05-29 | 2017-08-22 | Grünenthal GmbH | Tamper resistant dosage form with bimodal release profile |
| AU2014289187B2 (en) | 2013-07-12 | 2019-07-11 | Grunenthal Gmbh | Tamper-resistant dosage form containing ethylene-vinyl acetate polymer |
| AU2014356581C1 (en) | 2013-11-26 | 2020-05-28 | Grunenthal Gmbh | Preparation of a powdery pharmaceutical composition by means of cryo-milling |
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| MX2016014738A (es) | 2014-05-12 | 2017-03-06 | Gruenenthal Gmbh | Formulacion en capsula de liberacion inmediata resistente a alteraciones que comprende tapentadol. |
| CN106456550A (zh) | 2014-05-26 | 2017-02-22 | 格吕伦塔尔有限公司 | 避免乙醇剂量倾泻的多颗粒 |
| 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 |
| PL3169666T3 (pl) | 2014-07-15 | 2019-03-29 | Grünenthal GmbH | Podstawione pochodne azaspiro(4,5)dekanu |
| JP2018503693A (ja) | 2015-02-03 | 2018-02-08 | 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 | ポリエチレングリコールグラフトコポリマーを含む改変防止剤形 |
| BR112017021475A2 (pt) | 2015-04-24 | 2018-07-10 | Gruenenthal Gmbh | forma de dosagem resistente à adulteração (tamper) com liberação imediata e resistência contra extração de solvente |
| CA2998259A1 (en) | 2015-09-10 | 2017-03-16 | Grunenthal Gmbh | Protecting oral overdose with abuse deterrent immediate release formulations |
| KR20180108567A (ko) | 2015-10-22 | 2018-10-04 | 주노 테라퓨틱스 게엠베하 | 형질도입을 위한 방법, 키트, 제제 및 장치 |
| AU2017294524A1 (en) | 2016-07-06 | 2018-12-20 | Grünenthal 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
- 2004-12-21 BR BRPI0418052A patent/BRPI0418052A2/pt not_active Application Discontinuation
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- 2004-12-21 RU RU2006126787/04A patent/RU2383544C2/ru not_active IP Right Cessation
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- 2004-12-21 CN CN2004800420360A patent/CN1922189B/zh not_active Expired - Fee Related
- 2004-12-21 PL PL04804136T patent/PL1725567T3/pl unknown
- 2004-12-21 HR HR20080272T patent/HRP20080272T3/xx unknown
- 2004-12-21 WO PCT/EP2004/014539 patent/WO2005066183A1/de not_active Ceased
- 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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2005
- 2005-01-03 PE PE2005000023A patent/PE20050758A1/es not_active Application Discontinuation
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2006
- 2006-06-21 IL IL176457A patent/IL176457A/en not_active IP Right Cessation
- 2006-06-21 EC EC2006006667A patent/ECSP066667A/es unknown
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- 2006-07-24 NO NO20063422A patent/NO337127B1/no not_active IP Right Cessation
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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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