ZA200606252B - Methods for making 3-O-protected morphinones and 3-O-protected morphinone dienol carboxylates - Google Patents
Methods for making 3-O-protected morphinones and 3-O-protected morphinone dienol carboxylates Download PDFInfo
- Publication number
- ZA200606252B ZA200606252B ZA200606252A ZA200606252A ZA200606252B ZA 200606252 B ZA200606252 B ZA 200606252B ZA 200606252 A ZA200606252 A ZA 200606252A ZA 200606252 A ZA200606252 A ZA 200606252A ZA 200606252 B ZA200606252 B ZA 200606252B
- Authority
- ZA
- South Africa
- Prior art keywords
- alkyl
- compound
- formula
- base
- cio
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 53
- -1 3-O-protected morphinone dienol carboxylates Chemical class 0.000 title description 10
- 150000001875 compounds Chemical class 0.000 claims description 65
- 125000000217 alkyl group Chemical group 0.000 claims description 59
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical group CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 30
- 239000000203 mixture Substances 0.000 claims description 22
- 239000000460 chlorine Substances 0.000 claims description 17
- YRIZYWQGELRKNT-UHFFFAOYSA-N 1,3,5-trichloro-1,3,5-triazinane-2,4,6-trione Chemical compound ClN1C(=O)N(Cl)C(=O)N(Cl)C1=O YRIZYWQGELRKNT-UHFFFAOYSA-N 0.000 claims description 14
- 229950009390 symclosene Drugs 0.000 claims description 14
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 13
- 229910052801 chlorine Inorganic materials 0.000 claims description 13
- 125000006239 protecting group Chemical group 0.000 claims description 13
- 239000003153 chemical reaction reagent Substances 0.000 claims description 12
- 150000001299 aldehydes Chemical class 0.000 claims description 11
- 150000002576 ketones Chemical class 0.000 claims description 11
- 150000003333 secondary alcohols Chemical class 0.000 claims description 11
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 8
- YMWUJEATGCHHMB-UHFFFAOYSA-N dichloromethane Natural products ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 8
- 239000003960 organic solvent Substances 0.000 claims description 7
- 150000003138 primary alcohols Chemical class 0.000 claims description 7
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 6
- 125000003118 aryl group Chemical group 0.000 claims description 6
- 239000003795 chemical substances by application Substances 0.000 claims description 5
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 3
- 239000002253 acid Substances 0.000 claims description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 2
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 claims 8
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims 8
- HPYNZHMRTTWQTB-UHFFFAOYSA-N 2,3-dimethylpyridine Chemical compound CC1=CC=CN=C1C HPYNZHMRTTWQTB-UHFFFAOYSA-N 0.000 claims 6
- JRNVZBWKYDBUCA-UHFFFAOYSA-N N-chlorosuccinimide Chemical compound ClN1C(=O)CCC1=O JRNVZBWKYDBUCA-UHFFFAOYSA-N 0.000 claims 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims 5
- 150000001412 amines Chemical class 0.000 claims 4
- PSHKMPUSSFXUIA-UHFFFAOYSA-N n,n-dimethylpyridin-2-amine Chemical compound CN(C)C1=CC=CC=N1 PSHKMPUSSFXUIA-UHFFFAOYSA-N 0.000 claims 4
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims 4
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims 3
- KEQGZUUPPQEDPF-UHFFFAOYSA-N 1,3-dichloro-5,5-dimethylimidazolidine-2,4-dione Chemical compound CC1(C)N(Cl)C(=O)N(Cl)C1=O KEQGZUUPPQEDPF-UHFFFAOYSA-N 0.000 claims 2
- ZKQDCIXGCQPQNV-UHFFFAOYSA-N Calcium hypochlorite Chemical compound [Ca+2].Cl[O-].Cl[O-] ZKQDCIXGCQPQNV-UHFFFAOYSA-N 0.000 claims 2
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 claims 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 claims 2
- CEJLBZWIKQJOAT-UHFFFAOYSA-N dichloroisocyanuric acid Chemical compound ClN1C(=O)NC(=O)N(Cl)C1=O CEJLBZWIKQJOAT-UHFFFAOYSA-N 0.000 claims 2
- UHOVQNZJYSORNB-UHFFFAOYSA-N monobenzene Natural products C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 claims 2
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 claims 1
- DURPTKYDGMDSBL-UHFFFAOYSA-N 1-butoxybutane Chemical compound CCCCOCCCC DURPTKYDGMDSBL-UHFFFAOYSA-N 0.000 claims 1
- JWUJQDFVADABEY-UHFFFAOYSA-N 2-methyltetrahydrofuran Chemical compound CC1CCCO1 JWUJQDFVADABEY-UHFFFAOYSA-N 0.000 claims 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 claims 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 1
- AUHZEENZYGFFBQ-UHFFFAOYSA-N mesitylene Substances CC1=CC(C)=CC(C)=C1 AUHZEENZYGFFBQ-UHFFFAOYSA-N 0.000 claims 1
- 125000001827 mesitylenyl group Chemical group [H]C1=C(C(*)=C(C([H])=C1C([H])([H])[H])C([H])([H])[H])C([H])([H])[H] 0.000 claims 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 1
- 239000008096 xylene Substances 0.000 claims 1
- 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 16
- QMMFVYPAHWMCMS-UHFFFAOYSA-N Dimethyl sulfide Chemical compound CSC QMMFVYPAHWMCMS-UHFFFAOYSA-N 0.000 description 12
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 11
- 238000006243 chemical reaction Methods 0.000 description 9
- OROGSEYTTFOCAN-DNJOTXNNSA-N codeine Chemical compound C([C@H]1[C@H](N(CC[C@@]112)C)C3)=C[C@H](O)[C@@H]1OC1=C2C3=CC=C1OC OROGSEYTTFOCAN-DNJOTXNNSA-N 0.000 description 9
- 238000006859 Swern oxidation reaction Methods 0.000 description 7
- XYYVYLMBEZUESM-CMKMFDCUSA-N codeinone Chemical compound C([C@H]1[C@H](N(CC[C@@]112)C)C3)=CC(=O)[C@@H]1OC1=C2C3=CC=C1OC XYYVYLMBEZUESM-CMKMFDCUSA-N 0.000 description 7
- XYYVYLMBEZUESM-UHFFFAOYSA-N dihydrocodeine Natural products C1C(N(CCC234)C)C2C=CC(=O)C3OC2=C4C1=CC=C2OC XYYVYLMBEZUESM-UHFFFAOYSA-N 0.000 description 7
- 229930013053 morphinan alkaloid Natural products 0.000 description 6
- 229960005181 morphine Drugs 0.000 description 6
- 229920006395 saturated elastomer Polymers 0.000 description 6
- OROGSEYTTFOCAN-UHFFFAOYSA-N hydrocodone Natural products C1C(N(CCC234)C)C2C=CC(O)C3OC2=C4C1=CC=C2OC OROGSEYTTFOCAN-UHFFFAOYSA-N 0.000 description 5
- 229960004126 codeine Drugs 0.000 description 4
- NFDFQCUYFHCNBW-SCGPFSFSSA-N dienestrol Chemical compound C=1C=C(O)C=CC=1\C(=C/C)\C(=C\C)\C1=CC=C(O)C=C1 NFDFQCUYFHCNBW-SCGPFSFSSA-N 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 3
- 230000000202 analgesic effect Effects 0.000 description 3
- 239000006227 byproduct Substances 0.000 description 3
- FQXXSQDCDRQNQE-UHFFFAOYSA-N markiertes Thebain Natural products COC1=CC=C2C(N(CC3)C)CC4=CC=C(OC)C5=C4C23C1O5 FQXXSQDCDRQNQE-UHFFFAOYSA-N 0.000 description 3
- PFBSOANQDDTNGJ-YNHQPCIGSA-N morphinone Chemical compound O([C@H]1C(C=C[C@H]23)=O)C4=C5[C@@]12CCN(C)[C@@H]3CC5=CC=C4O PFBSOANQDDTNGJ-YNHQPCIGSA-N 0.000 description 3
- 230000003647 oxidation Effects 0.000 description 3
- 238000007254 oxidation reaction Methods 0.000 description 3
- 230000001590 oxidative effect Effects 0.000 description 3
- 125000000075 primary alcohol group Chemical group 0.000 description 3
- 239000000376 reactant Substances 0.000 description 3
- 150000003462 sulfoxides Chemical class 0.000 description 3
- 229930003945 thebaine Natural products 0.000 description 3
- FQXXSQDCDRQNQE-VMDGZTHMSA-N thebaine Chemical compound C([C@@H](N(CC1)C)C2=CC=C3OC)C4=CC=C(OC)C5=C4[C@@]21[C@H]3O5 FQXXSQDCDRQNQE-VMDGZTHMSA-N 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- 239000004215 Carbon black (E152) Substances 0.000 description 2
- 238000005675 Corey-Kim oxidation reaction Methods 0.000 description 2
- BRUQQQPBMZOVGD-XFKAJCMBSA-N Oxycodone Chemical compound O=C([C@@H]1O2)CC[C@@]3(O)[C@H]4CC5=CC=C(OC)C2=C5[C@@]13CCN4C BRUQQQPBMZOVGD-XFKAJCMBSA-N 0.000 description 2
- UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 description 2
- 230000010933 acylation Effects 0.000 description 2
- 238000005917 acylation reaction Methods 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 229930195733 hydrocarbon Natural products 0.000 description 2
- 150000002430 hydrocarbons Chemical class 0.000 description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- NUJOXMJBOLGQSY-UHFFFAOYSA-N manganese dioxide Chemical compound O=[Mn]=O NUJOXMJBOLGQSY-UHFFFAOYSA-N 0.000 description 2
- 229960004127 naloxone Drugs 0.000 description 2
- UZHSEJADLWPNLE-GRGSLBFTSA-N naloxone Chemical compound O=C([C@@H]1O2)CC[C@@]3(O)[C@H]4CC5=CC=C(O)C2=C5[C@@]13CCN4CC=C UZHSEJADLWPNLE-GRGSLBFTSA-N 0.000 description 2
- DQCKKXVULJGBQN-XFWGSAIBSA-N naltrexone Chemical compound N1([C@@H]2CC3=CC=C(C=4O[C@@H]5[C@](C3=4)([C@]2(CCC5=O)O)CC1)O)CC1CC1 DQCKKXVULJGBQN-XFWGSAIBSA-N 0.000 description 2
- 229960003086 naltrexone Drugs 0.000 description 2
- CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 2
- 229960002085 oxycodone Drugs 0.000 description 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
- MLVMHYBEWQXNNS-OEUJKCCCSA-N (4R,4aR,7aR,12bS)-9-acetyl-9-hydroxy-3-methyl-2,4,4a,7a,10,13-hexahydro-1H-4,12-methanobenzofuro[3,2-e]isoquinolin-7-one Chemical compound C(C)(=O)C1(CC=C2C[C@@H]3[C@@H]4C=CC([C@H]5[C@@]4(C2=C1O5)CCN3C)=O)O MLVMHYBEWQXNNS-OEUJKCCCSA-N 0.000 description 1
- PQORVHDYUUYHSR-VBVDBJQASA-N (4r,4ar,7ar,12bs)-3-methyl-9-phenylmethoxy-1,2,4,4a,7a,13-hexahydro-4,12-methanobenzofuro[3,2-e]isoquinoline-7-one Chemical compound O([C@@H]1[C@]23CCN([C@H](C4)[C@@H]3C=CC1=O)C)C1=C2C4=CC=C1OCC1=CC=CC=C1 PQORVHDYUUYHSR-VBVDBJQASA-N 0.000 description 1
- BUAKPITZELZWNI-UHFFFAOYSA-N 1-chlorocyclohexene Chemical compound ClC1=CCCCC1 BUAKPITZELZWNI-UHFFFAOYSA-N 0.000 description 1
- CJPDBKNETSCHCH-UHFFFAOYSA-N 1-methylsulfinyldodecane Chemical compound CCCCCCCCCCCCS(C)=O CJPDBKNETSCHCH-UHFFFAOYSA-N 0.000 description 1
- GMLREHXYJDLZOU-LEPYJNQMSA-N 3-Acetylmorphine Chemical compound O([C@H]1[C@H](C=C[C@H]23)O)C4=C5[C@@]12CCN(C)[C@@H]3CC5=CC=C4OC(C)=O GMLREHXYJDLZOU-LEPYJNQMSA-N 0.000 description 1
- LMCSMHJWQWMKAE-UHFFFAOYSA-N 6-methylsulfinylhexanoic acid Chemical compound CS(=O)CCCCCC(O)=O LMCSMHJWQWMKAE-UHFFFAOYSA-N 0.000 description 1
- FSNCEEGOMTYXKY-JTQLQIEISA-N Lycoperodine 1 Natural products N1C2=CC=CC=C2C2=C1CN[C@H](C(=O)O)C2 FSNCEEGOMTYXKY-JTQLQIEISA-N 0.000 description 1
- SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 1
- 150000001204 N-oxides Chemical class 0.000 description 1
- UQCNKQCJZOAFTQ-ISWURRPUSA-N Oxymorphone Chemical compound O([C@H]1C(CC[C@]23O)=O)C4=C5[C@@]12CCN(C)[C@@H]3CC5=CC=C4O UQCNKQCJZOAFTQ-ISWURRPUSA-N 0.000 description 1
- 240000001090 Papaver somniferum Species 0.000 description 1
- 230000003042 antagnostic effect Effects 0.000 description 1
- RDJGWRFTDZZXSM-RNWLQCGYSA-N benzylmorphine Chemical compound O([C@@H]1[C@]23CCN([C@H](C4)[C@@H]3C=C[C@@H]1O)C)C1=C2C4=CC=C1OCC1=CC=CC=C1 RDJGWRFTDZZXSM-RNWLQCGYSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 150000007942 carboxylates Chemical class 0.000 description 1
- PQANGXXSEABURG-UHFFFAOYSA-N cyclohex-2-en-1-ol Chemical group OC1CCCC=C1 PQANGXXSEABURG-UHFFFAOYSA-N 0.000 description 1
- FWFSEYBSWVRWGL-UHFFFAOYSA-N cyclohex-2-enone Chemical compound O=C1CCCC=C1 FWFSEYBSWVRWGL-UHFFFAOYSA-N 0.000 description 1
- 125000001475 halogen functional group Chemical group 0.000 description 1
- LLPOLZWFYMWNKH-CMKMFDCUSA-N hydrocodone Chemical compound C([C@H]1[C@H](N(CC[C@@]112)C)C3)CC(=O)[C@@H]1OC1=C2C3=CC=C1OC LLPOLZWFYMWNKH-CMKMFDCUSA-N 0.000 description 1
- 229960000240 hydrocodone Drugs 0.000 description 1
- WVLOADHCBXTIJK-YNHQPCIGSA-N hydromorphone Chemical compound O([C@H]1C(CC[C@H]23)=O)C4=C5[C@@]12CCN(C)[C@@H]3CC5=CC=C4O WVLOADHCBXTIJK-YNHQPCIGSA-N 0.000 description 1
- 229960001410 hydromorphone Drugs 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- PWBJWDKDPAPGED-UHFFFAOYSA-N n'-chlorobutanediamide Chemical compound NC(=O)CCC(=O)NCl PWBJWDKDPAPGED-UHFFFAOYSA-N 0.000 description 1
- 239000007800 oxidant agent Substances 0.000 description 1
- 229960005118 oxymorphone Drugs 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 239000000955 prescription drug Substances 0.000 description 1
- 230000001737 promoting effect Effects 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- OSBSFAARYOCBHB-UHFFFAOYSA-N tetrapropylammonium Chemical compound CCC[N+](CCC)(CCC)CCC OSBSFAARYOCBHB-UHFFFAOYSA-N 0.000 description 1
- LLPOLZWFYMWNKH-UHFFFAOYSA-N trans-dihydrocodeinone Natural products C1C(N(CCC234)C)C2CCC(=O)C3OC2=C4C1=CC=C2OC LLPOLZWFYMWNKH-UHFFFAOYSA-N 0.000 description 1
- MDDPTCUZZASZIQ-UHFFFAOYSA-N tris[(2-methylpropan-2-yl)oxy]alumane Chemical compound [Al+3].CC(C)(C)[O-].CC(C)(C)[O-].CC(C)(C)[O-] MDDPTCUZZASZIQ-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D489/00—Heterocyclic compounds containing 4aH-8, 9 c- Iminoethano-phenanthro [4, 5-b, c, d] furan ring systems, e.g. derivatives of [4, 5-epoxy]-morphinan of the formula:
- C07D489/02—Heterocyclic compounds containing 4aH-8, 9 c- Iminoethano-phenanthro [4, 5-b, c, d] furan ring systems, e.g. derivatives of [4, 5-epoxy]-morphinan of the formula: with oxygen atoms attached in positions 3 and 6, e.g. morphine, morphinone
-
- 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
- A61P25/04—Centrally acting analgesics, e.g. opioids
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- 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
- C07D491/22—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 four or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/18—Compounds having one or more C—Si linkages as well as one or more C—O—Si linkages
- C07F7/1804—Compounds having Si-O-C linkages
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Neurosurgery (AREA)
- Life Sciences & Earth Sciences (AREA)
- Neurology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pain & Pain Management (AREA)
- Pharmacology & Pharmacy (AREA)
- Biomedical Technology (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Catalysts (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Steroid Compounds (AREA)
- Saccharide Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US54271104P | 2004-02-06 | 2004-02-06 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ZA200606252B true ZA200606252B (en) | 2007-11-28 |
Family
ID=34860329
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ZA200606252A ZA200606252B (en) | 2004-02-06 | 2006-07-28 | Methods for making 3-O-protected morphinones and 3-O-protected morphinone dienol carboxylates |
Country Status (34)
| Country | Link |
|---|---|
| US (6) | US8003793B2 (no) |
| EP (3) | EP2194059A3 (no) |
| JP (1) | JP4963968B2 (no) |
| KR (4) | KR20070108956A (no) |
| CN (1) | CN1918168B (no) |
| AP (1) | AP2006003716A0 (no) |
| AT (2) | ATE406372T1 (no) |
| AU (1) | AU2005212258B2 (no) |
| BR (1) | BRPI0506607B8 (no) |
| CA (2) | CA2808199C (no) |
| CR (1) | CR8590A (no) |
| CY (2) | CY1108506T1 (no) |
| DE (2) | DE602005009321D1 (no) |
| DK (2) | DK1864987T3 (no) |
| EA (2) | EA016062B1 (no) |
| EC (1) | ECSP066824A (no) |
| ES (2) | ES2313299T3 (no) |
| GE (1) | GEP20084454B (no) |
| HK (2) | HK1119160A1 (no) |
| HR (2) | HRP20080618T3 (no) |
| IL (2) | IL177281A (no) |
| MA (1) | MA28346A1 (no) |
| MX (1) | MXPA06008931A (no) |
| NO (2) | NO20063989L (no) |
| NZ (2) | NZ548786A (no) |
| PL (2) | PL1864987T3 (no) |
| PT (2) | PT1864987E (no) |
| RS (2) | RS50663B (no) |
| SG (1) | SG150500A1 (no) |
| SI (2) | SI1711502T1 (no) |
| TN (1) | TNSN06248A1 (no) |
| UA (2) | UA88646C2 (no) |
| WO (1) | WO2005077957A2 (no) |
| ZA (1) | ZA200606252B (no) |
Families Citing this family (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ES2313299T3 (es) | 2004-02-06 | 2009-03-01 | Euro-Celtique S.A. | Procedimientos para producir morfinonas 3 o protegidas y carboxilatos de morfinona dienol 3 o protegidos. |
| CA2663909A1 (en) * | 2006-09-20 | 2008-03-27 | Mallinckrodt Inc. | Preparation of substituted morphinan-6-ones and salts and intermediates thereof |
| CA2707757C (en) * | 2007-03-06 | 2017-01-03 | Peter X. Wang | Process for the preparation of quaternary n-alkyl morphinan alkaloid salts |
| US9040726B2 (en) * | 2007-03-06 | 2015-05-26 | Mallinckrodt Llc | Process for the preparation of quaternary N-alkyl morphinan alkaloid salts |
| CA2726220C (en) * | 2008-05-27 | 2017-03-28 | Mallinckrodt Inc. | Processes and compounds for the preparation of normorphinans |
| US9458109B2 (en) * | 2008-09-03 | 2016-10-04 | Mallinckrodt Llc | Substituted berbines and processes for their synthesis |
| US9700508B2 (en) | 2010-05-10 | 2017-07-11 | Euro-Celtique S.A. | Pharmaceutical compositions comprising hydromorphone and naloxone |
| WO2011141490A1 (en) | 2010-05-10 | 2011-11-17 | Euro-Celtique S.A. | Combination of active loaded granules with additional actives |
| BR112012028788A2 (pt) | 2010-05-10 | 2016-07-19 | Euro Celtique Sa | fabricação de grânulos sem ativos |
| EP3068397A1 (en) | 2013-11-13 | 2016-09-21 | Euro-Celtique S.A. | Hydromorphone and naloxone for treatment of pain and opioid bowel dysfunction syndrome |
| WO2017057460A1 (ja) * | 2015-09-30 | 2017-04-06 | 富士フイルムファインケミカルズ株式会社 | 有機化合物の製造方法 |
Family Cites Families (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2654756A (en) * | 1949-10-20 | 1953-10-06 | Mallinckrodt Chemical Works | Process of preparing codeinone, dihydrocodeinone, and dihydromorphinone |
| DE902257C (de) | 1951-07-17 | 1954-01-21 | Knoll Ag | Verfahren zur Herstellung von Acylderivaten der Enolform des Codeinons |
| GB1495271A (en) * | 1974-04-10 | 1977-12-14 | Macfarlan Smith Ltd | Dehydrohalogenation of codeinone derivatives |
| US4472253A (en) * | 1981-08-17 | 1984-09-18 | The Florida Board Of Regents On Behalf Of The Florida State University | Process for the preparation of an N-substituted 3-O-alkyl-14-hydroxynormorphinone derivative |
| US5112975A (en) * | 1984-03-27 | 1992-05-12 | Mallinckrodt Specialty Chemicals Company | Preparation of noroxymorphone from morphine |
| SE9003665D0 (sv) * | 1990-11-16 | 1990-11-16 | Kabivitrum Ab | Morphine prodrugs |
| GB9116909D0 (en) * | 1991-08-06 | 1991-09-18 | Salford Ultrafine Chem & Res | Morphine derivatives |
| US5821374A (en) * | 1995-11-21 | 1998-10-13 | Hoffmann-La Roche Inc. | Process for the oxidation of alcohols |
| US5869669A (en) * | 1996-07-26 | 1999-02-09 | Penick Corporation | Preparation of 14-hydroxynormorphinones from normorphinone dienol acylates |
| GB9713703D0 (en) * | 1997-06-30 | 1997-09-03 | Johnson Matthey Plc | Preparation of opiates |
| US6177567B1 (en) | 1999-10-15 | 2001-01-23 | Boehringer Ingelheim Chemicals, Inc. | Method for preparing oxycodone |
| US6596877B2 (en) * | 2001-10-17 | 2003-07-22 | Novartis Ag | Accelerated process for preparing O-methyl phenols, N-methyl heteroaromatic compounds, and methylated aminophenols |
| ES2313299T3 (es) | 2004-02-06 | 2009-03-01 | Euro-Celtique S.A. | Procedimientos para producir morfinonas 3 o protegidas y carboxilatos de morfinona dienol 3 o protegidos. |
-
2005
- 2005-02-04 ES ES05712726T patent/ES2313299T3/es active Active
- 2005-02-04 MX MXPA06008931A patent/MXPA06008931A/es active IP Right Grant
- 2005-02-04 CA CA2808199A patent/CA2808199C/en active Active
- 2005-02-04 AP AP2006003716A patent/AP2006003716A0/xx unknown
- 2005-02-04 KR KR1020077025207A patent/KR20070108956A/ko not_active Application Discontinuation
- 2005-02-04 NZ NZ548786A patent/NZ548786A/en unknown
- 2005-02-04 EP EP09015220A patent/EP2194059A3/en not_active Withdrawn
- 2005-02-04 RS RSP-2008/0553A patent/RS50663B/sr unknown
- 2005-02-04 ES ES07014411T patent/ES2338054T3/es active Active
- 2005-02-04 SI SI200530468T patent/SI1711502T1/sl unknown
- 2005-02-04 US US10/588,637 patent/US8003793B2/en active Active
- 2005-02-04 PL PL07014411T patent/PL1864987T3/pl unknown
- 2005-02-04 PL PL05712726T patent/PL1711502T3/pl unknown
- 2005-02-04 RS RSP-2010/0064A patent/RS51317B/sr unknown
- 2005-02-04 EA EA200801811A patent/EA016062B1/ru not_active IP Right Cessation
- 2005-02-04 KR KR1020097016500A patent/KR101011460B1/ko active IP Right Grant
- 2005-02-04 SI SI200530925T patent/SI1864987T1/sl unknown
- 2005-02-04 EP EP05712726A patent/EP1711502B1/en active Active
- 2005-02-04 EP EP07014411A patent/EP1864987B1/en active Active
- 2005-02-04 PT PT07014411T patent/PT1864987E/pt unknown
- 2005-02-04 CA CA2555215A patent/CA2555215C/en active Active
- 2005-02-04 PT PT05712726T patent/PT1711502E/pt unknown
- 2005-02-04 JP JP2006552236A patent/JP4963968B2/ja active Active
- 2005-02-04 AT AT05712726T patent/ATE406372T1/de active
- 2005-02-04 DK DK07014411.8T patent/DK1864987T3/da active
- 2005-02-04 GE GEAP20059608A patent/GEP20084454B/en unknown
- 2005-02-04 KR KR1020077025206A patent/KR100921695B1/ko active IP Right Grant
- 2005-02-04 AT AT07014411T patent/ATE451374T1/de active
- 2005-02-04 EA EA200601394A patent/EA012905B1/ru not_active IP Right Cessation
- 2005-02-04 BR BRPI0506607A patent/BRPI0506607B8/pt active IP Right Grant
- 2005-02-04 SG SG200900838-4A patent/SG150500A1/en unknown
- 2005-02-04 NZ NZ565355A patent/NZ565355A/en unknown
- 2005-02-04 CN CN2005800040830A patent/CN1918168B/zh active Active
- 2005-02-04 DE DE602005009321T patent/DE602005009321D1/de active Active
- 2005-02-04 AU AU2005212258A patent/AU2005212258B2/en active Active
- 2005-02-04 DK DK05712726T patent/DK1711502T3/da active
- 2005-02-04 DE DE602005018265T patent/DE602005018265D1/de active Active
- 2005-02-04 WO PCT/US2005/003390 patent/WO2005077957A2/en active Application Filing
- 2005-02-04 UA UAA200704105A patent/UA88646C2/uk unknown
- 2005-04-02 UA UAA200609622A patent/UA87833C2/uk unknown
-
2006
- 2006-07-28 ZA ZA200606252A patent/ZA200606252B/en unknown
- 2006-08-03 IL IL177281A patent/IL177281A/en active IP Right Grant
- 2006-08-04 MA MA29240A patent/MA28346A1/fr unknown
- 2006-08-04 TN TNP2006000248A patent/TNSN06248A1/fr unknown
- 2006-09-01 CR CR8590A patent/CR8590A/es unknown
- 2006-09-05 EC EC2006006824A patent/ECSP066824A/es unknown
- 2006-09-05 KR KR1020067018113A patent/KR100921696B1/ko active IP Right Grant
- 2006-09-06 NO NO20063989A patent/NO20063989L/no not_active Application Discontinuation
-
2007
- 2007-04-18 HK HK08106459.3A patent/HK1119160A1/xx unknown
- 2007-04-18 HK HK07104100.2A patent/HK1103071A1/xx unknown
-
2008
- 2008-11-12 CY CY20081101295T patent/CY1108506T1/el unknown
- 2008-11-26 HR HR20080618T patent/HRP20080618T3/xx unknown
-
2010
- 2010-02-25 CY CY20101100178T patent/CY1109838T1/el unknown
- 2010-03-05 HR HR20100123T patent/HRP20100123T1/hr unknown
- 2010-05-06 IL IL205596A patent/IL205596A/en active IP Right Grant
-
2011
- 2011-07-22 US US13/189,228 patent/US8198444B2/en active Active
-
2012
- 2012-05-15 US US13/472,227 patent/US8685996B2/en active Active
-
2014
- 2014-02-24 US US14/188,430 patent/US8975257B2/en active Active
-
2015
- 2015-03-02 NO NO20150276A patent/NO339083B1/no unknown
- 2015-03-03 US US14/637,129 patent/US9670218B2/en not_active Expired - Fee Related
-
2017
- 2017-05-04 US US15/587,118 patent/US20170233400A1/en not_active Abandoned
Also Published As
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| ZA200606252B (en) | Methods for making 3-O-protected morphinones and 3-O-protected morphinone dienol carboxylates | |
| AU2008201587B2 (en) | Methods for making 3-O-protected morphinones and 3-O-protected morphinone dienol carboxylates |