NO314585B1 - Pyrazolpyrimidinoner som hemmer cyklisk guanosin-3',5'- monofosfatfosfodiesterase type 5 (cGMP PDE5), for behandling av seksuell dysfunksjon - Google Patents

Info

Publication number

NO314585B1

NO314585B1 NO19995211A NO995211A NO314585B1 NO 314585 B1 NO314585 B1 NO 314585B1 NO 19995211 A NO19995211 A NO 19995211A NO 995211 A NO995211 A NO 995211A NO 314585 B1 NO314585 B1 NO 314585B1

Authority

NO

Norway

Prior art keywords

preparation

pyrimidin

title compound

pyrazolo

dihydro

Prior art date

1997-04-25

Links

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• Global Dossier
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• ZOOGRGPOEVQQDX-UUOKFMHZSA-N 3',5'-cyclic GMP Chemical compound C([C@H]1O2)OP(O)(=O)O[C@H]1[C@@H](O)[C@@H]2N1C(N=C(NC2=O)N)=C2N=C1 ZOOGRGPOEVQQDX-UUOKFMHZSA-N 0.000 title claims description 20
• ZOOGRGPOEVQQDX-UHFFFAOYSA-N cyclic GMP Natural products O1C2COP(O)(=O)OC2C(O)C1N1C=NC2=C1NC(N)=NC2=O ZOOGRGPOEVQQDX-UHFFFAOYSA-N 0.000 title description 14
• 238000011282 treatment Methods 0.000 title description 6
• 230000002401 inhibitory effect Effects 0.000 title description 3
• RGTMHUKTLKJHNW-UHFFFAOYSA-N 1H-pyrazole 1H-pyrimidin-2-one Chemical class N1C(N=CC=C1)=O.N1N=CC=C1 RGTMHUKTLKJHNW-UHFFFAOYSA-N 0.000 title 1
• 101100189582 Dictyostelium discoideum pdeD gene Proteins 0.000 title 1
• 101150098694 PDE5A gene Proteins 0.000 title 1
• 201000001880 Sexual dysfunction Diseases 0.000 title 1
• 102000011016 Type 5 Cyclic Nucleotide Phosphodiesterases Human genes 0.000 title 1
• 108010037581 Type 5 Cyclic Nucleotide Phosphodiesterases Proteins 0.000 title 1
• 102100029175 cGMP-specific 3',5'-cyclic phosphodiesterase Human genes 0.000 title 1
• 231100000872 sexual dysfunction Toxicity 0.000 title 1
• 238000002360 preparation method Methods 0.000 claims description 486
• 150000001875 compounds Chemical class 0.000 claims description 430
• 238000000034 method Methods 0.000 claims description 239
• -1 1-oxidopyridinyl Chemical group 0.000 claims description 100
• 230000002829 reductive effect Effects 0.000 claims description 83
• 239000000203 mixture Substances 0.000 claims description 69
• 150000003839 salts Chemical class 0.000 claims description 45
• 239000012453 solvate Substances 0.000 claims description 29
• 229910052757 nitrogen Inorganic materials 0.000 claims description 26
• 239000000460 chlorine Substances 0.000 claims description 22
• 239000003814 drug Substances 0.000 claims description 19
• 125000000623 heterocyclic group Chemical group 0.000 claims description 14
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 14
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 13
• 206010004446 Benign prostatic hyperplasia Diseases 0.000 claims description 12
• 208000004403 Prostatic Hyperplasia Diseases 0.000 claims description 12
• 125000004433 nitrogen atom Chemical group N* 0.000 claims description 12
• 125000004193 piperazinyl group Chemical group 0.000 claims description 12
• 125000001424 substituent group Chemical group 0.000 claims description 11
• 201000001068 Prinzmetal angina Diseases 0.000 claims description 10
• 238000004519 manufacturing process Methods 0.000 claims description 10
• 125000001425 triazolyl group Chemical group 0.000 claims description 10
• 229910052736 halogen Inorganic materials 0.000 claims description 9
• 238000007363 ring formation reaction Methods 0.000 claims description 9
• 206010057671 Female sexual dysfunction Diseases 0.000 claims description 8
• 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 8
• 125000002883 imidazolyl group Chemical group 0.000 claims description 8
• 125000002757 morpholinyl group Chemical group 0.000 claims description 8
• 208000010228 Erectile Dysfunction Diseases 0.000 claims description 7
• 241001465754 Metazoa Species 0.000 claims description 7
• 229940123333 Phosphodiesterase 5 inhibitor Drugs 0.000 claims description 7
• 238000009472 formulation Methods 0.000 claims description 7
• 150000002367 halogens Chemical class 0.000 claims description 7
• 201000001881 impotence Diseases 0.000 claims description 7
• 239000002590 phosphodiesterase V inhibitor Substances 0.000 claims description 7
• 238000011321 prophylaxis Methods 0.000 claims description 7
• 201000001320 Atherosclerosis Diseases 0.000 claims description 6
• 206010071445 Bladder outlet obstruction Diseases 0.000 claims description 6
• 206010007559 Cardiac failure congestive Diseases 0.000 claims description 6
• 206010013935 Dysmenorrhoea Diseases 0.000 claims description 6
• 208000010412 Glaucoma Diseases 0.000 claims description 6
• 206010019280 Heart failures Diseases 0.000 claims description 6
• 206010020772 Hypertension Diseases 0.000 claims description 6
• 206010021639 Incontinence Diseases 0.000 claims description 6
• 208000018262 Peripheral vascular disease Diseases 0.000 claims description 6
• 206010036600 Premature labour Diseases 0.000 claims description 6
• 206010039085 Rhinitis allergic Diseases 0.000 claims description 6
• 208000006011 Stroke Diseases 0.000 claims description 6
• 208000003800 Urinary Bladder Neck Obstruction Diseases 0.000 claims description 6
• 201000009961 allergic asthma Diseases 0.000 claims description 6
• 201000010105 allergic rhinitis Diseases 0.000 claims description 6
• 208000006673 asthma Diseases 0.000 claims description 6
• 206010006451 bronchitis Diseases 0.000 claims description 6
• 229910052801 chlorine Inorganic materials 0.000 claims description 6
• 208000023819 chronic asthma Diseases 0.000 claims description 6
• 201000010099 disease Diseases 0.000 claims description 6
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 6
• 230000008991 intestinal motility Effects 0.000 claims description 6
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 6
• 239000008194 pharmaceutical composition Substances 0.000 claims description 6
• 208000002815 pulmonary hypertension Diseases 0.000 claims description 6
• 125000004076 pyridyl group Chemical group 0.000 claims description 6
• 206010002388 Angina unstable Diseases 0.000 claims description 5
• 208000007718 Stable Angina Diseases 0.000 claims description 5
• 208000007814 Unstable Angina Diseases 0.000 claims description 5
• 208000009325 Variant Angina Pectoris Diseases 0.000 claims description 5
• 230000015572 biosynthetic process Effects 0.000 claims description 5
• 238000009109 curative therapy Methods 0.000 claims description 5
• 229940079593 drug Drugs 0.000 claims description 5
• 201000004332 intermediate coronary syndrome Diseases 0.000 claims description 5
• 125000000842 isoxazolyl group Chemical group 0.000 claims description 5
• 125000001715 oxadiazolyl group Chemical group 0.000 claims description 5
• 230000008569 process Effects 0.000 claims description 5
• 125000003373 pyrazinyl group Chemical group 0.000 claims description 5
• 125000003226 pyrazolyl group Chemical group 0.000 claims description 5
• 125000002098 pyridazinyl group Chemical group 0.000 claims description 5
• 125000000714 pyrimidinyl group Chemical group 0.000 claims description 5
• 125000000335 thiazolyl group Chemical group 0.000 claims description 5
• ZYHQGITXIJDDKC-UHFFFAOYSA-N 2-[2-(2-aminophenyl)ethyl]aniline Chemical group NC1=CC=CC=C1CCC1=CC=CC=C1N ZYHQGITXIJDDKC-UHFFFAOYSA-N 0.000 claims description 4
• 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 4
• 239000003085 diluting agent Substances 0.000 claims description 4
• 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 4
• 125000004307 pyrazin-2-yl group Chemical group [H]C1=C([H])N=C(*)C([H])=N1 0.000 claims description 4
• 125000002206 pyridazin-3-yl group Chemical group [H]C1=C([H])C([H])=C(*)N=N1 0.000 claims description 4
• 125000000246 pyrimidin-2-yl group Chemical group [H]C1=NC(*)=NC([H])=C1[H] 0.000 claims description 4
• 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 3
• 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims description 3
• 125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 claims description 3
• 208000006399 Premature Obstetric Labor Diseases 0.000 claims description 3
• 125000003545 alkoxy group Chemical group 0.000 claims description 3
• 230000017531 blood circulation Effects 0.000 claims description 3
• 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 claims description 3
• 125000001309 chloro group Chemical group Cl* 0.000 claims description 3
• 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 3
• 125000003386 piperidinyl group Chemical group 0.000 claims description 3
• 208000026440 premature labor Diseases 0.000 claims description 3
• 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 3
• 125000001607 1,2,3-triazol-1-yl group Chemical group [*]N1N=NC([H])=C1[H] 0.000 claims description 2
• 125000001766 1,2,4-oxadiazol-3-yl group Chemical group [H]C1=NC(*)=NO1 0.000 claims description 2
• 125000003626 1,2,4-triazol-1-yl group Chemical group [*]N1N=C([H])N=C1[H] 0.000 claims description 2
• DRIPPBPKPZJMRK-UHFFFAOYSA-N 1-[(1-methylimidazol-2-yl)methyl]-5-[5-(4-methylpiperazin-1-yl)sulfonyl-2-propoxyphenyl]-3-propyl-4h-pyrazolo[4,3-d]pyrimidin-7-one Chemical compound CCCOC1=CC=C(S(=O)(=O)N2CCN(C)CC2)C=C1C(NC(=O)C=12)=NC=1C(CCC)=NN2CC1=NC=CN1C DRIPPBPKPZJMRK-UHFFFAOYSA-N 0.000 claims description 2
• NIBCDDKWFDEBEP-UHFFFAOYSA-N 3-ethyl-5-[5-(4-ethylpiperazin-1-yl)sulfonyl-2-propoxyphenyl]-2-(pyridin-2-ylmethyl)-4h-pyrazolo[4,3-d]pyrimidin-7-one Chemical compound CCCOC1=CC=C(S(=O)(=O)N2CCN(CC)CC2)C=C1C(NC1=C2CC)=NC(=O)C1=NN2CC1=CC=CC=N1 NIBCDDKWFDEBEP-UHFFFAOYSA-N 0.000 claims description 2
• 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 2
• 125000004800 4-bromophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Br 0.000 claims description 2
• 125000004195 4-methylpiperazin-1-yl group Chemical group [H]C([H])([H])N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 claims description 2
• UYAYUQTWQGZTRW-UHFFFAOYSA-N 5-[5-(4-ethylpiperazin-1-yl)sulfonyl-2-propoxyphenyl]-3-propyl-2-(pyrazin-2-ylmethyl)-4h-pyrazolo[4,3-d]pyrimidin-7-one Chemical compound CCCOC1=CC=C(S(=O)(=O)N2CCN(CC)CC2)C=C1C(NC(=O)C1=N2)=NC1=C(CCC)N2CC1=CN=CC=N1 UYAYUQTWQGZTRW-UHFFFAOYSA-N 0.000 claims description 2
• OQYWVCNPOTZBOU-UHFFFAOYSA-N 5-[5-(4-ethylpiperazin-1-yl)sulfonyl-2-propoxyphenyl]-3-propyl-2-(pyridazin-3-ylmethyl)-4h-pyrazolo[4,3-d]pyrimidin-7-one Chemical compound CCCOC1=CC=C(S(=O)(=O)N2CCN(CC)CC2)C=C1C(NC(=O)C1=N2)=NC1=C(CCC)N2CC1=CC=CN=N1 OQYWVCNPOTZBOU-UHFFFAOYSA-N 0.000 claims description 2
• AFXWHZNUUIIFFR-UHFFFAOYSA-N 5-[5-(4-ethylpiperazin-1-yl)sulfonyl-2-propoxyphenyl]-3-propyl-2-(pyridin-2-ylmethyl)-4h-pyrazolo[4,3-d]pyrimidin-7-one Chemical compound CCCOC1=CC=C(S(=O)(=O)N2CCN(CC)CC2)C=C1C(NC(=O)C1=N2)=NC1=C(CCC)N2CC1=CC=CC=N1 AFXWHZNUUIIFFR-UHFFFAOYSA-N 0.000 claims description 2
• ORWIHWJJQPOUJI-UHFFFAOYSA-N 5-[5-[4-(2-hydroxyethyl)piperazin-1-yl]sulfonyl-2-propoxyphenyl]-3-propyl-1-(pyridin-2-ylmethyl)-4h-pyrazolo[4,3-d]pyrimidin-7-one Chemical compound CCCOC1=CC=C(S(=O)(=O)N2CCN(CCO)CC2)C=C1C(NC=1C(CCC)=N2)=NC(=O)C=1N2CC1=CC=CC=N1 ORWIHWJJQPOUJI-UHFFFAOYSA-N 0.000 claims description 2
• 125000000217 alkyl group Chemical group 0.000 claims description 2
• MDFFNEOEWAXZRQ-UHFFFAOYSA-N aminyl Chemical compound [NH2] MDFFNEOEWAXZRQ-UHFFFAOYSA-N 0.000 claims description 2
• 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 2
• 125000004850 cyclobutylmethyl group Chemical group C1(CCC1)C* 0.000 claims description 2
• UKJLNMAFNRKWGR-UHFFFAOYSA-N cyclohexatrienamine Chemical group NC1=CC=C=C[CH]1 UKJLNMAFNRKWGR-UHFFFAOYSA-N 0.000 claims description 2
• 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims description 2
• 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 2
• 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims description 2
• 125000000636 p-nitrophenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)[N+]([O-])=O 0.000 claims description 2
• 125000004353 pyrazol-1-yl group Chemical group [H]C1=NN(*)C([H])=C1[H] 0.000 claims description 2
• 125000004940 pyridazin-4-yl group Chemical group N1=NC=C(C=C1)* 0.000 claims description 2
• 125000004527 pyrimidin-4-yl group Chemical group N1=CN=C(C=C1)* 0.000 claims description 2
• 125000004528 pyrimidin-5-yl group Chemical group N1=CN=CC(=C1)* 0.000 claims description 2
• 125000005843 halogen group Chemical group 0.000 claims 2
• 230000035876 healing Effects 0.000 claims 2
• 125000000753 cycloalkyl group Chemical group 0.000 claims 1
• 229940126601 medicinal product Drugs 0.000 claims 1
• 239000007787 solid Substances 0.000 description 169
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 144
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 137
• 239000000243 solution Substances 0.000 description 107
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 87
• 239000006260 foam Substances 0.000 description 73
• PVOAHINGSUIXLS-UHFFFAOYSA-N 1-Methylpiperazine Chemical compound CN1CCNCC1 PVOAHINGSUIXLS-UHFFFAOYSA-N 0.000 description 55
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 53
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 52
• 239000011541 reaction mixture Substances 0.000 description 41
• HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 39
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 34
• 238000004440 column chromatography Methods 0.000 description 34
• VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 33
• 239000000741 silica gel Substances 0.000 description 33
• 229910002027 silica gel Inorganic materials 0.000 description 33
• WGCYRFWNGRMRJA-UHFFFAOYSA-N 1-ethylpiperazine Chemical compound CCN1CCNCC1 WGCYRFWNGRMRJA-UHFFFAOYSA-N 0.000 description 32
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 28
• CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 27
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 27
• 238000010992 reflux Methods 0.000 description 25
• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 24
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 22
• 238000006243 chemical reaction Methods 0.000 description 21
• VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 21
• ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 20
• 239000002904 solvent Substances 0.000 description 20
• 239000000725 suspension Substances 0.000 description 19
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 18
• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 18
• 239000003480 eluent Substances 0.000 description 18
• 239000003921 oil Substances 0.000 description 18
• 235000019198 oils Nutrition 0.000 description 18
• WFCSWCVEJLETKA-UHFFFAOYSA-N 2-piperazin-1-ylethanol Chemical compound OCCN1CCNCC1 WFCSWCVEJLETKA-UHFFFAOYSA-N 0.000 description 17
• 239000011734 sodium Substances 0.000 description 17
• YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 17
• JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 16
• 239000012458 free base Substances 0.000 description 16
• 239000000284 extract Substances 0.000 description 15
• 239000000843 powder Substances 0.000 description 15
• 102000004861 Phosphoric Diester Hydrolases Human genes 0.000 description 14
• 108090001050 Phosphoric Diester Hydrolases Proteins 0.000 description 14
• HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 14
• FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 14
• 238000001816 cooling Methods 0.000 description 13
• 238000010828 elution Methods 0.000 description 13
• DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 12
• 239000008346 aqueous phase Substances 0.000 description 12
• KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 12
• 239000012074 organic phase Substances 0.000 description 12
• BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 12
• 238000002425 crystallisation Methods 0.000 description 11
• 230000008025 crystallization Effects 0.000 description 11
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• YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 10
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• 239000002253 acid Substances 0.000 description 10
• 239000002585 base Substances 0.000 description 10
• 239000012267 brine Substances 0.000 description 10
• 239000000706 filtrate Substances 0.000 description 10
• HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 10
• WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 9
• 102100024085 Alpha-aminoadipic semialdehyde dehydrogenase Human genes 0.000 description 9
• SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 9
• 101710135349 Venom phosphodiesterase Proteins 0.000 description 9
• QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Natural products N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 9
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• NJWIMFZLESWFIM-UHFFFAOYSA-N 2-(chloromethyl)pyridine Chemical compound ClCC1=CC=CC=N1 NJWIMFZLESWFIM-UHFFFAOYSA-N 0.000 description 8
• KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 8
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• WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 8
• 239000012043 crude product Substances 0.000 description 8
• 238000001914 filtration Methods 0.000 description 8
• 239000002244 precipitate Substances 0.000 description 8
• UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 8
• 238000003756 stirring Methods 0.000 description 8
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical group CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 7
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• WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 6
• 230000029936 alkylation Effects 0.000 description 6
• 239000003153 chemical reaction reagent Substances 0.000 description 6
• 239000000543 intermediate Substances 0.000 description 6
• BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 6
• JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 6
• RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 5
• DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 5
• 239000007864 aqueous solution Substances 0.000 description 5
• 210000005226 corpus cavernosum Anatomy 0.000 description 5
• LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 5
• 229910052708 sodium Inorganic materials 0.000 description 5
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