TW524805B - Pyrazolo[4,3-d]pyrimidine-7-one compounds having the effect of inhibiting phosphodiesterase (PDE-5) and the preparation processes, intermediates and pharmaceutical compositions or veterinary formulations thereof - Google Patents

Pyrazolo[4,3-d]pyrimidine-7-one compounds having the effect of inhibiting phosphodiesterase (PDE-5) and the preparation processes, intermediates and pharmaceutical compositions or veterinary formulations thereof Download PDF

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TW524805B
TW524805B TW87102657A TW87102657A TW524805B TW 524805 B TW524805 B TW 524805B TW 87102657 A TW87102657 A TW 87102657A TW 87102657 A TW87102657 A TW 87102657A TW 524805 B TW524805 B TW 524805B
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TW87102657A
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Mark Edward Bunnage
John Paul Mathias
Stephen Derek Albert Street
Anthony Wood
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Pfizer
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Abstract

Compounds of formulae (IA) and (IB): or pharmaceutically or veterinarily acceptable salts thereof, or pharmaceutically or veterinarily acceptable solvates of either entity, wherein R1 is C1 to C3 alkyl substituted with C3 to C6 cycloalkyl, CONR5R6 or a N-linked heterocyclic group; (CH2)nHet or (CH2)nAr; R2 is C1 to C6 alkyl; R3 is C1 to C6 alkyl optionally substituted with C1 to C4 alkoxy; R4 is SO2NR7R8; R5 and R6 are each independently selected from H and C1 to C4 alkyl optionally substituted with C1 to C4 alkoxy, or, together with the nitrogen atom to which they are attached, form a 5- or 6-membered heterocyclic group; R7 and R8, together with the nitrogen atom to which they are attached, form a 4-R10-piperazinyl group; R10 is H or C1 to C4 alkyl optionally substituted with OH, C1 to C4 alkoxy or CONH2; Het is an optionally substituted C-linked 5- or 6-membered heterocyclic group; Ar is optionally substituted phenyl; and n is 0 or 1; are potent and selective cGMP PDE5 inhibitors useful in the treatment of, inter alia, male erectile dysfunction and female sexual dysfunction.

Description

524805 A7 B7 五、發明説明（2 ) 或其藥學上或獸醫學上可接受之鹽類，或其藥學上或獸醫 學上可接受之溶劑合物， ‘ 其中 111爲（：1— C3 烷基，（CH2)nHet 或 ^ C Η 2 ) η Α Γ ，其中該Cl 一 C3院基係經C3 - 〇6環 烷基，C〇N R 5 R 6或以N -連結之雜環基所取代，此雜 環基係選自吡唑基，咪唑基，三唑基，吡咯啶基，六氫吡 陡基，嗎啉基（morpholinyl)及4 一 R9 —六氫吼哄基； (CH2)nHet 或（CH2)nAr; R2爲Ci — C6院基； R 3爲選擇性經c i 一 C 4烷氧基所取代之c i — C 6烷 基； R 4 爲 S 〇 2 N R 7 R 8 ; R 5與R 6係分別選自Η及選擇性經C i 一 C 4烷氧基所 取代之CX-C4烷基，或者R5與R6連同與其連接之氮原 子形成吼咯D定基，六氫吼u定基，嗎啉基或4 - R 9 -六氫批 哄基； 經濟部中央標準局員工消費合作社印製 f衣-- (請先閱讀背面之注意事項再填寫本頁) # R7與R8連同與其相接之氮原子形成4 一 R1C) —六氫 吡畊基； R9爲Ci — 〇4院基； R 1 ◦爲Η或選擇性經〇Η，C i 一 C 4烷氧基或 C〇N Η 2所取代之C i — C 4烷基； H e t爲含有一或二個氮原子之C 一連結的六員雜環 基（可選擇性呈其單-N-氧化物形式）或爲含有一至四 個選自氮，氧及硫之雜原子的C 一連結的五員雜環基，其 本纸張尺度適用中國國家標準（CNS ) A4規格（210x297公釐）-5 - 524805 A7 --- B7 " 一~—----------—------------—' 五、發明説明（3 ) 中無論爲前述六員或五員雜環基，均可選擇性經一或二個 選自c i 一 C 4烷基（可選擇性經c i — C 4烷氧基所取代之 )’ c i 一 c 4烷氧基，鹵基及N Η 2所取代； A r爲選擇性經一或二個選自C i 一 C 4烷基，C i 一 C4 烷氧基，鹵基，〇Ν，CONH2，N〇2，NH2， NHS〇2 (Ci—Cd烷基）及S〇2NH2所取代之苯基 :且 η爲〇或1 〇 在以上之定義中除非另有指明，否則含有三個或三個 以上碳原子的烷基及烷氧基可爲直鏈或具支鏈者，鹵基係 指氟，氯，溴或碘。 經濟部中央標準局員工消費合作社印製 (讀先閱讀背面之注意事項存填寫本頁) 式（I A )與（I Β )化合物可含有一或多個對掌中 心（chiral center)，因此可呈立體異構物（即鏡像異構物 (enantiomers)或非鏡像異構物（diastereoisomers)及其 混合物。本發明包括式（I A )與（I B )化合物的該兩 種個別立體異構物及其任意混合物。非鏡像異構物的分離 可透過慣用技術達成，例如將式（I A )或（I B )化合 物的非鏡像異構物混合物或其適當鹽類或衍生物以分段結 晶（fractional crystallization)或層析法（包括 Η P L C )加以分離。式（I A )或（I Β )化合物的個別鏡像異 構物可由對應的純旋光性中間物製備，或藉析解（ resolimon)的方式（可透過使用適當的對掌性載質對消旋 物進行Η P L C或於適當情況下把消旋物與適當的旋光性 酸或鹼之間的反應所形成的非鏡像異構鹽加以分段結晶） 本紙張尺度適用中國國家標準（CNS ) Α4規格（210X29*7公釐） -6 - 524805 A7 _JB7___ 五、發明説明（4 ) 製備之。 式（I A )與（I B )化合物也可呈互變異構（ tautomeric )形態，而且本發明也包括兩者的互變異構混合 物及個別的互變異構物。 式（I A )與（I B )化合物經過放射標記之衍生物 (適於生物硏究）也包括在本發明範掘內。 含有鹼性中心之式（I A )與（I B )化合物的藥學 上或獸醫學上可接受鹽舉例而言爲與無機酸（如氫氯酸， 氫溴酸，硫酸及磷酸），有機羧酸或有機磺酸所形成的無 毒性酸加成鹽。式（I A )與（I B )化合物也可與鹼形 成藥學上或獸醫學上可接受之金屬鹽，尤其是無毒性的驗 金屬鹽，其例子包括鈉鹽與鉀鹽。 較佳的鹽類爲檸檬酸鹽。 經濟部中央標率局員工消費合作社印製 (請先閱讀背面之注意事項再填寫本頁) 式（I A )奠（I B )化合物中較佳者爲R 1係經C 3 一 C5環烷基，C〇NR5R6或N -連結之雜環基（選自 吡唑基，三唑基，嗎啉基及4 - R 9 -六氫吡畊基）所取代 iCi—Cs 烷基，（CH2)nHet 或（CH2)nAr ;R 5爲Η而R 6爲選擇性經C : 一 C 4烷氧基所取代之c丄 - C4烷基或者R5與R6連同與其連接之氮原子形成嗎啉 基；H e t係選自吡啶基，1 —氧吡啶基（1 · oxidopyridinyl )，嗒畊基，嘧啶基，吡畊基，咪唑基，異 口萼唑基，噻唑基，三唑基，及鳄二唑基，而任一者均可選 擇性經一或二個選自CH3，CH2CH2〇CH3， 〇CH3 及 NH2 所取代；且 R2，R3，R4，R9，Ar 本紙張尺度適用中國國家標準（CNS ) A4規格（210X297公楚1 Z 一 — ~~ 524805 A7 ______ B7 ___ 五、發明説明（5 ) 和η均如以上所定義者之化合物。 (請先閱讀背面之注意事項再填寫本頁) 式（I A )與（I Β )化合物中更佳者爲R 1係經環丁 基，C〇NR5R6，吡唑一1—基，1 ，2，3 —三唑一 1一基，l·，2，4 一三唑一 1 一基，嗎啉—4 一基，或 4 一甲基六氣吼哄一 1 一基所取代之C 1 一 C 2 k基’ C Η 2 H e t 或（CH2) nAr ; R2 爲 Ci 一 C3 院基’ R 3爲選擇性經C : 一 C 2烷氧基所取代之C i 一 C 3院基； R 5爲H而R 6爲選擇性經C i 一 C 2烷氧基所取代之C 1 一 C 2烷基或者R5與R6連同與其連接之氮原子形成嗎啉一 4 —基；R10爲選擇性經OH，〇CH3或CONH2單取 代之Cx— C2烷基；He t係選自吡啶—2 —基，1 一氧 口比n定一 2 —基，吼π定—3 -基，塔哄—3 —基，塔哄一 4 一基，嘧啶—4 一基，嘧啶—5 —基，吡畊一 2 —基，3 —甲氧吡啶一2 —基，6 —胺基吡啶一2 —基，1 一甲基 咪唑一2 —基，3，5 —二甲基異鳄唑一4 一基，2 —甲 基嘻π坐—4 一基，1 一甲基—1，2，4 一三哩一 5 —基 ，1— (2 —甲氧乙基）一1 ，2，4 —三唑一5 —基’ 經濟部中央標率局員工消費合作社印製 4 —甲基一1 ，2，4 —三唑一3 —基，3 —甲基一 1 ’ .2，4 —三唑—5 —基，1，2，4 —噚二唑一3 -基及 5 —甲基一 1，2，4 —噚二唑一 3 —基；Ar係選自苯 基，4 一氯苯基，4 一溴苯基，2 -氰苯基，2 -胺鑛基 苯基，4 一胺羰基苯基，2 -硝苯基，4 一硝苯基’ 2 一 胺苯基，4 一胺苯基，2 -甲烷磺醯胺苯基，4 一甲院磺 醯胺苯基，4 一乙烷磺醯胺苯基，4—(丙一 2 -基院磺 本紙張尺度適用中國國家標準（CNS ) A4規格（210X297公釐） 524805 A7 B7 五、發明説明（6 ) 醯胺基）苯基，及4 -胺烷磺醯基苯基；且η係如先前所 定義者之化合物。 式（I A )與（I Β )化合物中特佳者爲R 1係環丁基 甲基，嗎琳一 4 —基鑛甲基’ 2 —（嗎琳一 4 一基）乙基 ，嘧啶—2 —基，CH2He t 或（CH2) nAr ; R2係 CH2CH3 或 CH2CH2CH3 ; R3 爲 CH2CH3， CH2CH2CH3 或 CH2CH2〇CH3 ; R10 爲 CH3 ，CH2CHs或CH2CH2〇H ; He t係選自吡啶一2 一基，嗒畊一 3 —基，吡畊一2 —基，3 —甲氧吡啶一 2 —基，6 —胺吡啶—2 —基，1—甲基咪唑一 2 —基，3 ，5—二甲基異噚唑一4 —基，1—甲基一1 ，2，4 — 三唑一5 —基，1— (2 —甲氧乙基）一1 ，2，4 —三 唑—5 —基及5 —甲基一1，2，4 —噚二唑一3 —基； A r爲選自苯基，’2 -胺苯基，2 -甲烷磺醯胺苯基，4 一甲烷磺醯胺苯基，4 一乙烷磺醯胺苯基及4 一（丙一 2 -基院礦酿胺基）苯基；且π係如以上所疋義者之化合物 0 經濟部中央標準局員工消費合作社印製 (請先閱讀背面之注意事項再填寫本頁) 本發明中尤佳之化合物包括： 5 — {5 —〔4 — (2 —羥乙基）六氫吡畊一 1—基 磺醯基〕一 2 -正丙氧苯基} — 3 -正丙基一 1_ (吡啶 —2 —基）甲基一 1，6 —二氫一 7H —吡唑並〔4，3 一 d〕嘧啶—7 —酮； 1— (1 一甲基咪唑一2 —基）甲基一5 —〔5—（ 4一甲基六氫吡畊一1一基磺醯基）一2—正丙氧苯基〕 本纸張尺度適用中國國家標準（CNS ) A4規格（210X297公釐） -9 - 524805 Μ Β7 五、發明説明（7 ) —3 —正丙基—1，6 -二氫—7Η -吡唑並〔4，3 — d〕嘧啶—7 —酮； 5 — { 5 —〔4 一（2 —羥乙基）六氫吡畊一 1—基 磺醯基〕一 2 -正丙氧苯基} 一 3 -正丙基一 2 -（吡D定 —2 —基）甲基一 2，6 —二氫—7H —吡唑並〔4，3 —d〕嘧D定一 7 —酮； 5 -〔5 — (4 —乙基六氫吡哄—1—基磺醯基）一 2 —正丙氧苯基〕一 3 —正丙基一 2—(吡啶一 2 -基） 甲基一 2，6 —二氫一7H —吡唑並〔4，3 — d〕嘧D定 —7 —酮； 3 —乙基一5 —〔5 —（4 —乙基六氫吡畊一1 一基 礦釀基）一2 —正丙氧苯基〕一 2 —（吼卩定一 2 —基）甲 基-2，6—二氫—7H —吡唑並〔4，3 — d〕嘧啶― 7 —酮； · 5 —〔5 — (4 —乙基六氫吼哄一 1 一基磺醯基）— 2 -正丙氧苯基〕一 3 -正丙基—2 -（塔哄—3 —基） 經濟部中央標準局員工消費合作社印？木 (請先閲讀背面之注意事項再填寫本頁) 甲基一2，6 —二氫一7H —吡唑並〔4，3 — d〕嘧D定 -7 -酮； 5 —〔5 — (4 —乙基六氫吡畊一 1—基磺醯基）— 2 -正丙氧苯基〕一 3 —正丙基一 2-（塔畊基—2 —基 )甲基—2，6 —二氫—7 Η —吡唑並〔4，3 — d〕喃 口定一 7 —酮；以及 5 —〔2 —乙氧基一5 — (4 —乙氧六氫吡畊一 1 — 基磺醯基）苯基〕—3 -正丙基—2 -（吡啶一 2 -基） 本紙張尺度適用中國國家標準（CNS ) A4規格（210X297公釐） _彳〇 _ 524805 經濟部中央標準局t貝工消費合作社印繁 ΑΊ B7 五、發明説明（8 ) 甲基一 2，6 —二氫一7H —吡唑並〔4，3 — d〕嘧啶 —酮。 本發明另一方面提出式（I A)與式（I B )化合物 ，其藥學上或獸醫學上可接受鹽類及其藥學上或獸醫學上 可接受之溶劑合物等的製備方法，如以下之說明。 熟習此項技藝者會知道對這些製法提供某種程度上的 說明後，所用合成步驟的順序可加以變更’而且這些步驟 的順序尤其仍須視多項因素而定，如特定基質中所含其他 官能基的本質（nature )，關鍵中間物是否易於取得，以 及即將採用的保護基策略（如果有）。而這些因素也顯然 會影響到此等合成步驟所用試劑的選擇。 保護基策略的說明係如以下實施例之合成途徑，在實 施例5 6中利用第三丁基二甲矽烷基之醇保護步驟是在所 要的N -甲磺醯化步驟之前，在實施例6 3中六氫吡哄4 -位置係經B 〇 c (第三丁氧羰基）保護以阻止該六氫吡 畊的雙磺醯化，而在實施例2 3與6 8中利用三甲基乙酶 基之胺保護步驟是在倒數第二個氯磺酸化步驟之前。 此外也應知道的是，在某些式（I A )與式（I B ) 化合物中各種不同的標準取代基或官能基的互相轉化（ interconversions)與轉變（transformations)會得到其他式 (I A)與式（I B)化合物。其例子包括5 -苯基取代 基2 —位置之烷氧基（alkoxide )互換（見實施例4 1至 實施例4 2之轉化），氰基水解爲胺羰基（見實施例4 6 至實施例4 7之轉化），硝基還原爲胺基（見實施例4 9 (請先閱讀背面之注意事項再填寫本頁) 装· 、11 本纸張尺度適用中國國家標準（CNS ) A4規格（210χ297公楚） -11 - 5248〇5 A7 i'發明説明（9) ’ 5〇，5i，91，115，118，121 分別轉化 至實施例 52，53，54，93，116，119， 1 2 2 )，胺基的磺醯化（見實施例5 2，5 4，1 1 6 ’ 1 1 9，1 1 2分別轉化至實施例5 5，5 7，1 1 7 ’ 12〇，123，124)，鹵基的氫解（見實施例 8 8至實施例8 7之轉化），以及吡啶基的N -氧化（見 實施例6，1 2分別轉化至實施例1 2 8，1 2 9 )。 此外，某些式（I A )與式（I B )化合物可直接由 其對應的4 一未取代六氫吡畊同系物，即式（I A )與式 (I B )化合物中R 1 ^爲氫者，依標準烷化步驟製得。 以下製程係可用於製得本發明化合物大槪合成步驟之 說明。 1 ·式（I A )或式（I B )化合物可分別由式（ H A )或（Π B )_化合物與式（m )化合物反應而製得 (請先閱讀背面之注意事項再填寫本頁) 經濟部中央標準局員工消費合作社印繁524805 A7 B7 V. Description of the invention (2) or a pharmaceutically or veterinarily acceptable salt thereof, or a pharmaceutically or veterinarily acceptable solvate thereof, wherein '111 is (: 1-C3 alkyl , (CH2) nHet or ^ C Η 2) η Α Γ, wherein the Cl-C3 radical is substituted by C3--O6 cycloalkyl, CONR 5R6 or N-linked heterocyclic group, The heterocyclic group is selected from pyrazolyl, imidazolyl, triazolyl, pyrrolidinyl, hexahydropyridyl, morpholinyl and 4-R9-hexahydrocarbyl; (CH2) nHet or (CH2) nAr; R2 is Ci—C6 courtyard; R3 is ci—C6 alkyl optionally substituted by ci—C4 alkoxy; R4 is S〇2 NR 7 R 8; R 5 and R 6 is selected from the group consisting of Η and CX-C4 alkyl optionally substituted by C i -C 4 alkoxy, or R 5 and R 6 together with the nitrogen atom attached to them form a C-D amidyl group, a hexahydro-A amidyl group, Morpholine or 4-R 9 -hexahydropyridine; printed f-shirts by the Consumer Cooperatives of the Central Bureau of Standards of the Ministry of Economic Affairs-(Please read the notes on the back before filling this page) # R7 and R8 together with it Nitrogen atom formation 4 -R1C)-hexahydropyridyl; R9 is Ci-〇4 courtyard; R 1 ◦ is Η or C i substituted by 〇Η, C i -C 4 alkoxy or CON Η 2 — C 4 alkyl; Het is a C-linked six-membered heterocyclic group containing one or two nitrogen atoms (optionally in its mono-N-oxide form) or one to four selected from nitrogen, The C-linked five-membered heterocyclic group of oxygen and sulfur heteroatoms, the paper size of this paper applies to the Chinese National Standard (CNS) A4 specification (210x297 mm) -5-524805 A7 --- B7 " one ~ — -------------------------- 'V. Description of Invention (3) Regardless of the aforementioned six-membered or five-membered heterocyclic group, the One or two selected from ci-C 4 alkyl (optionally substituted by ci-C 4 alkoxy) 'ci-c 4 alkoxy, halo and N Η 2; A r is selected One or two are selected from Ci-C4 alkyl, Ci-C4 alkoxy, halo, ON, CONH2, No2, NH2, NHS〇2 (Ci-Cd alkyl) and S 〇2NH2 substituted phenyl: and η is 0 or 1 〇 In the above definition, unless otherwise specified, contains three Alkyl and alkoxy groups of three or more carbon atoms may be linear or branched person, based halo refers to fluorine, chlorine, bromine or iodine. Printed by the Consumer Cooperatives of the Central Standards Bureau of the Ministry of Economic Affairs (read the precautions on the back and fill in this page) The compounds of formula (IA) and (IB) can contain one or more chiral centers, so they can be presented Stereoisomers (ie enantiomers or diastereoisomers) and mixtures thereof. The present invention includes these two individual stereoisomers of compounds of formula (IA) and (IB) and any of them Mixtures. Separation of non-image isomers can be achieved by conventional techniques, such as fractional crystallization of a mixture of non-image isomers of a compound of formula (IA) or (IB) or an appropriate salt or derivative thereof, or Chromatography (including Η PLC) to separate. Individual mirror image isomers of compounds of formula (IA) or (IB) can be prepared from the corresponding pure optically active intermediates, or by means of resolimon (resolimon) Appropriate pairing of the carrier with the racemateΗ PLC or, in appropriate cases, the non-mirromeric isomer salt formed by the reaction between the racemate and the appropriate optically active acid or base ） This paper size applies Chinese National Standard (CNS) A4 specification (210X29 * 7mm) -6-524805 A7 _JB7___ V. Description of the invention (4) It is prepared. The compounds of formula (IA) and (IB) can also exhibit mutual variation Tautomeric, and the invention also includes tautomeric mixtures of the two and individual tautomers. Radiolabeled derivatives of compounds of formula (IA) and (IB) (suitable for biological investigation) also include Within the scope of the present invention. Pharmaceutically or veterinarily acceptable salts of compounds of formulae (IA) and (IB) containing basic centers are, for example, with inorganic acids such as hydrochloric acid, hydrobromic acid, sulfuric acid and Phosphoric acid), non-toxic acid addition salts formed by organic carboxylic acids or organic sulfonic acids. Compounds of formula (IA) and (IB) can also form pharmaceutically or veterinarily acceptable metal salts with bases, especially non-toxic Examples of metal test salts include sodium and potassium salts. The preferred salts are citrates. Printed by the Consumer Cooperatives of the Central Standards Bureau of the Ministry of Economic Affairs (please read the precautions on the back before filling out this page). IA) compound (IB) Preferably, R 1 is a heterocyclic group linked through C 3 -C5 cycloalkyl, CONR 5R6 or N-(selected from pyrazolyl, triazolyl, morpholinyl, and 4-R 9 -hexahydropyridine ICi-Cs alkyl substituted by ()), (CH2) nHet or (CH2) nAr; R 5 is Η and R 6 is c 丄 -C4 alkyl or R5 optionally substituted by C: -C 4 alkoxy Forms morpholinyl with R6 and the nitrogen atom attached to it; Het is selected from pyridyl, 1-oxidopyridinyl, dacrotyl, pyrimidinyl, pyridoyl, imidazolyl, isoxazole Group, thiazolyl group, triazolyl group, and crocodiazolyl group, each of which may be optionally substituted with one or two members selected from CH3, CH2CH2, OCH3, OCH3 and NH2; and R2, R3, R4, R9, Ar This paper size applies to Chinese National Standard (CNS) A4 specifications (210X297 Gongchu 1 Z 1 ~ ~ 524805 A7 ______ B7 ___ V. Description of the invention (5) and η are compounds as defined above. (Please read the precautions on the back before filling out this page.) Among the compounds of formula (IA) and (IB), R 1 is more preferably cyclobutyl, CONR5R6, pyrazol 1-yl, 1, 2 , 3 -triazole- 1-yl, l ·, 2,4-triazole- 1-yl, morpholine-4-yl, or 4-methylhexazine-C1- C 2 k group 'C Η 2 Het or (CH2) nAr; R2 is Ci-C3 courtyard group; R 3 is C i -C 3 courtyard group optionally substituted by C: -C 2 alkoxy group; R 5 is H and R 6 is a C 1 -C 2 alkyl group optionally substituted by C i -C 2 alkoxy or R 5 and R 6 together with the nitrogen atom attached thereto form a morpholine 4- group; R 10 is selective Cx-C2 alkyl mono-substituted by OH, 0CH3 or CONH2; He t is selected from pyridin-2-yl, 1-oxyl ratio is n-2-yl, π-yl-3-yl, tower coo- 3-base, tower-base 4-base, pyrimidine-4 base, pyrimidine-5 base, pyrimidine 2-base, 3-methoxypyridine 2-base, 6-aminopyridine 2-base, 1-methylimidazol-2-yl, 3,5-dimethylisocrocodazole-4-yl, 2-methylhexyl 4-one, 1-methyl—1,2,4, one three-mile, one 5-based, 1— (2-methoxyethyl) —1,2,4-triazole—5-based 'Central Standard of the Ministry of Economic Affairs Lead bureau employee consumer cooperatives to print 4-methyl-1,2,4-triazole-3-yl, 3-methyl-1'.2,4-triazole-5-yl, 1,2,4- Oxadiazol-3-yl and 5-methyl-1,2,4- oxadiazol-3-yl; Ar is selected from phenyl, 4-chlorochloro, 4-bromophenyl, 2-cyanobenzene , 2-aminoamine phenyl, 4-monoaminocarbonylphenyl, 2-nitrophenyl, 4-mononitrophenyl '2-monoaminophenyl, 4-monoaminophenyl, 2-methanesulfonamidophenyl, 4 Yijiayuan sulfonamidophenyl, 4 monoethanesulfonamidophenyl, 4— (propylene-2-sulfonium sulfonate paper size applicable to Chinese National Standard (CNS) A4 specification (210X297 mm) 524805 A7 B7 5. Description of the invention (6) fluorenylamino) phenyl, and 4-aminoalkylsulfonylphenyl; and η is a compound as defined previously. Particularly preferred among the compounds of the formula (IA) and (IB) are R 1-based cyclobutylmethyl, morphine-4-yl group methyl '2-(morphine-4yl) ethyl, pyrimidine-2-yl , CH2He t or (CH2) nAr; R2 is CH2CH3 or CH2CH2CH3; R3 is CH2CH3, CH2CH2CH3 or CH2CH2〇CH3; R10 is CH3, CH2CHs or CH2CH2〇H; He t is selected from pyridyl-2 2-yl, dagen-1 -Yl, pyrenyl 2-yl, 3-methoxypyridine 2-yl, 6-aminopyridine 2-yl, 1-methylimidazole 2-yl, 3, 5-dimethylisoxazole 4-based, 1-methyl-1,2,4-triazole-5-yl, 1- (2-methoxyethyl) -1,2,4-triazole-5-yl and 5-methyl A 1,2,4-pyridadiazol-3-yl group; A r is selected from the group consisting of phenyl, '2-aminophenyl, 2-methanesulfonamidophenyl, 4 methanesulfonamidophenyl, 4 a Ethyl sulfonamide phenyl and 4- (propyl 2-aminoamine amine) phenyl; and π is a compound as defined above 0 Printed by the Consumer Cooperative of the Central Standards Bureau of the Ministry of Economic Affairs (please first (Read the notes on the back and fill out this page) In the present invention The preferred compounds include: 5 — {5 — [4 — (2-hydroxyethyl) hexahydropyridine—1-sulfofluorenyl] —2—n-propoxyphenyl} — 3—n-propyl-1— (pyridine —2 —yl) methyl-1,6-dihydro-7H —pyrazolo [4,3 —d] pyrimidin-7 —one; 1 — (1-methylimidazol-2-yl) methyl-5 — [5 -— (4-methylhexahydropyridine-1-ylsulfofluorenyl) —2-n-propoxyphenyl] This paper size applies to China National Standard (CNS) A4 (210X297 mm) -9 -524805 Μ B7 V. Description of the invention (7) —3 —n-propyl-1,6-dihydro-7Η-pyrazolo [4,3 — d] pyrimidin-7 —one; 5 — {5 — [4 Mono (2-hydroxyethyl) hexahydropyridine- 1-sulfosulfanyl] -2-n-propoxyphenyl} 3-n-propyl- 2-(pyridine-2-yl) methyl- 2,6-dihydro-7H-pyrazolo [4,3-d] pyrimidinyl-7-one; 5- [5- (4-ethylhexahydropyridin-1-ylsulfonyl)- 2-n-propoxyphenyl] -3-n-propyl-2- (pyridine-2-yl) methyl-2,6-dihydro-7H-pyrazolo 4,3 — d] pyrimidin-7-one; 3-ethyl-5 — [5 — (4-ethylhexahydropyridine-1 1-based mineral group) — 2-n-propoxyphenyl] 1 2-(sulidine 2 -yl) methyl-2,6-dihydro-7H-pyrazolo [4,3-d] pyrimidin-7-one; 5-[5-(4 -B Hexahydro hydrazine-1-1-sulfofluorenyl)-2-n-propoxyphenyl]-3-n-propyl-2-(tower-3-base) printed by the Consumers' Cooperative of the Central Standards Bureau of the Ministry of Economic Affairs? Wood (Please read the notes on the back before filling this page) Methyl-2,6-dihydro-7H-pyrazolo [4,3 — d] pyrimidin-7-one; 5 — [5 — ( 4-Ethylhexahydropyridine- 1-sulfosulfanyl) -2- 2-n-propoxyphenyl] -3-n-propyl-2- (takeryl-2-yl) methyl-2,6 — Dihydro-7, pyrene-pyrazolo [4,3-d], and 7-one; and 5- [2-ethoxy-6- (4-ethoxyhexahydropyridine 1-sulfone) Fluorenyl) phenyl] -3 -n-propyl-2-(pyridine-2-yl) This paper size is applicable to China National Standard (CNS) A4 (210X297 mm) _ 彳 〇_ 524805 Central Bureau of Standards, Ministry of Economic Affairs Shellfish Consumer Cooperatives Co., Ltd. Yinfan AΊ B7 V. Description of the invention (8) Methyl-2,6-dihydro-7H-pyrazolo [4,3-d] pyrimidin-one. Another aspect of the present invention proposes a method for preparing compounds of formula (IA) and formula (IB), pharmaceutically or veterinarily acceptable salts thereof, and pharmaceutically or veterinarily acceptable solvates thereof, as follows Instructions. Those skilled in the art will know that after providing a certain degree of explanation to these methods, the order of the synthetic steps used can be changed ', and the order of these steps especially depends on many factors, such as other functionalities contained in a particular matrix The nature of the base, whether key intermediates are easily accessible, and the protection base strategy (if any) to be adopted. These factors will obviously affect the choice of reagents used in these synthetic steps. The explanation of the protecting group strategy is as the synthetic route of the following example. The alcohol protection step using the third butyldisilyl group in Examples 5 and 6 is before the desired N-methanesulfonation step in Example 6. The 4-position of hexahydropyridine in 3 is protected by Boc (third butoxycarbonyl) to prevent the disulfonylation of the hexahydropyridine, and trimethylethyl is used in Examples 2 3 and 68. The enzyme-based amine protection step precedes the penultimate chlorosulfonation step. It should also be known that the interconversions and transformations of various different standard substituents or functional groups in certain compounds of formula (IA) and formula (IB) will yield other formulas (IA) and formulas. (IB) Compound. Examples include the 5-position substitution of alkoxide at the 2-phenyl substituent (see the conversion from Example 41 to Example 4 2), and the cyano group is hydrolyzed to the amine carbonyl group (see Example 46 to Example 6). Conversion of 4 to 7), reduction of nitro group to amine group (see Example 4 9 (please read the precautions on the back before filling in this page). ·· 11 This paper size applies Chinese National Standard (CNS) A4 specification (210χ297 (Gongchu) -11-5248〇5 A7 i 'Description of the Invention (9) '50, 5i, 91, 115, 118, 121 were respectively converted to Examples 52, 53, 54, 93, 116, 119, 1 2 2 ), The sulfonation of the amine group (see Example 5, 2, 5, 4, 1 1 6 '1 1 9, 1 1 2 respectively converted to Example 5 5, 5 7, 1 1 7' 12 0, 123, 124 ), The hydrogenolysis of the halogen group (see the conversion of Examples 88 to 7), and the N-oxidation of the pyridyl group (see the conversion of Examples 6, 12 to Examples 1 2 8 and 1 2 9) . In addition, certain compounds of formula (IA) and formula (IB) can be directly derived from their corresponding 4-unsubstituted hexahydropyrine homologues, that is, those compounds of formula (IA) and formula (IB) in which R 1 ^ is hydrogen, Prepared according to standard alkylation procedures. The following processes are used to illustrate the synthesis steps for the compounds of the present invention. 1. Compounds of formula (IA) or (IB) can be prepared by reacting compounds of formula (HA) or (Π B) _ with compounds of formula (m), respectively (please read the precautions on the back before filling this page) Ministry of Central Standards Bureau Employees Consumer Cooperatives

2Y ο S I /|\ 佳定 較所 爲中 基 氯 以 而 C ’ 式 基與 鹵 > 爲 A Y I 中 C 其式 1/ B T12Y ο S I / | \ Jiading is compared with the middle group chlorine and the C ′ formula and the halogen > is A Y I in the C formula 1 / B T1

R R ， 而者 IB)R R and IB)

如 係 3 R 與 2 RFor 3 R and 2 R

Η Ν 8 R 7 R 一驗 4 A \—/ 5 N C 準 標 家 國 一中 用 適 度 尺 i張 紙 i本Η Ν 8 R 7 R 1 test 4 A \ — / 5 N C quasi-standard home country No. 1 middle school uses a moderate ruler i paper i

I釐 公 7 9 2 X 2I cm 7 9 2 X 2

524805 A7 ___ B7 五、發明説明（1〇) 其中R 7與R8係如式（I A)與（I B)中所定義者。 此反應大致上是在室溫下且宜有適當溶劑如C i 一 C ； 烷醇的情況下利用過量式（ΠΙ )化合物或其他適當鹼以淸 除酸副產物（Η Y )下進行。 式（ΠΑ)或（ΠΒ)化合物可分別由式（IVA)或 (IV Β )化合物524805 A7 ___ B7 V. Description of the Invention (1) R 7 and R 8 are as defined in formulae (I A) and (I B). This reaction is generally carried out at room temperature and in the presence of a suitable solvent such as Ci-C; in the case of an alkanol, an excess of a compound of formula (III) or other suitable base is used to remove the acid by-product (ΗY). Compounds of formula (ΠA) or (ΠΒ) may be composed of compounds of formula (IVA) or (IV Β), respectively

(其中R1，R2與R3係如式（ΠΑ)與（ΠΒ)中所定 義者） 利用已知將S〇2Y基（其中Υ亦如式（ΠΑ)與（ΠΒ) 中所定義者）加入芳族環系統的方法製成。例如當Y爲氯 (請先閱讀背面之注意事項再填寫本頁) -裝·(Wherein R1, R2, and R3 are as defined in formulas (ΠΑ) and (ΠΒ)) S02Y group (where Υ is also defined as in formulas (ΠΑ) and (ΠΒ)) is added to the aromatic compound using known Family ring system method is made. For example, when Y is chlorine (please read the precautions on the back before filling this page)

、1T 經滴部中央標準局員工消費合作社印繁 擇 選物 再合 後化 用 } 作V 的 C 酸式 磺由 氯可 量物 過合 過化 透 } 下 。 B 溫之IV 室用 { 約作或 至氯 } OC 醯 A ο 硫IV 約量 C 在過式 ， 以 時性 本纸張尺度適用中國國家標準（CNS ) Α4規格（2ΚΓΧ297公釐）-13 - 524805 A7 B7 五、發明説明（ 〇1T is used by the Consumer Standards Cooperative of the Central Standards Bureau of Didi Ministry to select and recombine them and then combine them} C acid sulphur as V is converted from chlorine quantifiable compound and chemically converted}. B The temperature in the IV room is {about for or to chlorine} OC 醯 A ο sulfur IV about C in the formula, in time, this paper scale applies the Chinese National Standard (CNS) A4 specifications (2ΚΓ × 297 mm) -13- 524805 A7 B7 V. Description of the invention (〇

經濟部中央標準局員工消費合作社印¾ (其中R2與R3係如式（ΙΥΑ)或（IVB)中所定義者） 利用一或多種已知方法烷基化而製成，例如： (i )在有適當鹼並選擇性有碘化鈉或碘化鉀的情況 下於約一 7 0 °C至約.1 0 〇 °C之溫度令式（V )化合物與 式R 1 X化合物反應，其中R1係如式（IVA)與（IVB) 中所定義者，X爲適當離去基如鹵基（宜爲氯，溴或碘） ，Ci - C 4烷磺醯氧基，三氟甲烷磺醯氧基或芳基磺醯氧 基（如苯磺醯氧基或對甲苯磺醯氧基。此烷化反應宜在約 室溫至約8 0 °C之溫度下進行。 適當的鹼-溶劑組合可選自： (a )碳酸鈉，碳酸鉀或碳酸鉋，碳酸氫鈉或碳酸氫 鉀，或第三級胺如三乙胺或吡啶，連同C ! 一 C 4烷醇，1 ，2 —二甲氧乙烷，四氫呋喃，1 ，4 —二氧雜環己烷， 乙腈，吡啶’二甲基甲醯胺或N，N —二甲基乙醯胺； (b )氫氧化鈉或氫氧化鉀’或c i 一 C 4烷氧化鈉或 C 1 — C 4烷氧化鉀，連同c 1 一 C 4烷醇，水或其混合物； (c )氫化鋰，氫化鈉或氫化鉀，雙（三曱砂院基） 胺化鋰，雙（三甲矽烷基）胺化鈉或雙（三甲砍院基）胺 I (請先閱讀背面之注意事項再填寫本頁Printed by the Consumer Standards Cooperative of the Central Bureau of Standards of the Ministry of Economic Affairs (where R2 and R3 are as defined in formula (ΙΥΑ) or (IVB)) and are made by alkylation using one or more known methods, for example: (i) in With a suitable base and optionally with sodium iodide or potassium iodide, a compound of formula (V) is reacted with a compound of formula R 1 X at a temperature of about -70 ° C to about 100 ° C, where R1 is as As defined in formulae (IVA) and (IVB), X is a suitable leaving group such as halo (preferably chlorine, bromine or iodine), Ci-C 4 alkylsulfonyloxy, trifluoromethanesulfonyloxy or Arylsulfonyloxy (such as benzenesulfonyloxy or p-toluenesulfonyloxy). This alkylation reaction is preferably carried out at a temperature of about room temperature to about 80 ° C. A suitable base-solvent combination can be selected from : (A) Sodium carbonate, potassium carbonate or carbonate, sodium bicarbonate or potassium bicarbonate, or a tertiary amine such as triethylamine or pyridine, together with C! -C4 alkanol, 1,2-dimethoxyethyl Alkane, tetrahydrofuran, 1,4-dioxane, acetonitrile, pyridine 'dimethylformamide or N, N -dimethylacetamide; (b) sodium or potassium hydroxide' or ci One C 4 Sodium alkoxide or C 1 -C 4 potassium alkoxide, together with c 1 -C 4 alkanol, water or mixtures thereof; (c) lithium hydride, sodium hydride or potassium hydride, bis (trisaminyl) amination Lithium, bis (trimethylsilyl) amine or bis (trimethylsilyl) amine I (Please read the notes on the back before filling this page

、1T 本紙張尺度適用中國國家標準（CNS ) A4規格（210X297公釐） 524805 A7 B7 五、發明説明（12) 化鉀，二異丙基胺化鋰或丁基鋰，連同甲苯，乙醚（ether )’ 1，2 —二甲氧乙烷，四氫呋喃或1 ，4 —二氧雜環 己烷；或者 (d )在相轉移催化條件下，鹵化四烷基銨或氫氧化 四烷基銨，連同氫氧化鈉或氫氧化鉀水溶液與二氯甲烷， 1，2 -二氯乙烷或氯仿的混合物； (ϋ )依古典Mitsunobu方法令式（V )化合物與式 Ι^ΟΗ之化合物（其中R1係如式（IVA)與（IVB)中 所定義者）反應，典型的反應條件涉及在約- 5 °C至約室 溫之溫度且有三芳基膦及偶氮二羧酸二（Ci-Cd)烷酯 的情況下，在適當溶劑（如四氫呋喃或1，4 —二氧雜環 己烷）裡以該烷醇處理。 經濟部中央標準局員工消費合作社印製 某些較不易取得的式（IVA)與（IVB )化合物可用 較不直接的方式由枏關同系物以前述的烷基化方法得到， 例如製備例3 3 (其中R1爲2，4 一二氯嘧啶—5 —基甲 基）之氫解轉變爲製備例3 4 (其中R1爲嘧啶一 5 -基甲 基）。同樣地製備例102，103，104之醯胺與製 備例1 0 5，1 0 6，1 0 7之醯胺係分別由對應的製備 例1 0 1與製備例6 9羧酸製得的。 其他式（IVA)與（IVB)化合物中R1爲 C Η 2 H e t者可由吡哩並嘧啶酮-院化步驟之後雜環的構 建而製成。此一方式在所需H e t C Η 2 X無法取得時特別 方便。例如當He t爲3 —甲基一1，2，4 —三唑一5 一基或5 —甲基—1，2，4 一噚二唑—3 —基時，雜環 -15- (請先閱讀背面之注意事項再填寫本頁) 本紙張尺度適用中國國家標準（CNS ) A4規格（210X 297公釐） 524805 A7 B7 五、發明説明（13 ) 可分別由羧甲基前驅體或氰甲基前驅體（亦即R1爲 CH2C〇2H或CH2CN之式（IVA)與式（JVB)化 合物）以一系列慣用步驟構組而成。這些方式在製備例 6 9轉變爲製備例7 2以及製備例7 3，7 7轉變爲製備 例7 6，7 9有相關說明。 另一種取得式（IVA)與式（IVB )化合物的不同方 法是在合成路徑的早期階段把R 1基導入（例如產生一個 N 1 -或N 2 -經適當院化的吡哇衍生物），然後以類似於 後述式（W)至式（V)之轉化方式製成式（IVA)與式 (IV B )。 式（V )化合物可由式（VI )化合物 (請先閱讀背面之注意事項再填寫本頁)、 1T This paper size is applicable to Chinese National Standard (CNS) A4 specification (210X297 mm) 524805 A7 B7 5. Description of the invention (12) Potassium, lithium diisopropylamide or butyl lithium, together with toluene, ether (ether ) '1,2-dimethoxyethane, tetrahydrofuran or 1,4-dioxane; or (d) a tetraalkylammonium halide or tetraalkylammonium hydroxide under phase transfer catalysis conditions, together with A mixture of an aqueous sodium or potassium hydroxide solution with dichloromethane, 1,2-dichloroethane or chloroform; (ii) a compound of formula (V) and a compound of formula I ^ ΟΗ (where R1 is based on the classical Mitsunobu method); As defined by formula (IVA) and (IVB)), typical reaction conditions involve a temperature of about -5 ° C to about room temperature with triarylphosphine and azodicarboxylic acid di (Ci-Cd) In the case of an alkyl ester, the alkanol is treated in an appropriate solvent (such as tetrahydrofuran or 1,4-dioxane). Some of the less easily available compounds of formula (IVA) and (IVB) printed by the Consumer Cooperatives of the Central Standards Bureau of the Ministry of Economic Affairs can be obtained in a less direct way from Tongguan homologues using the aforementioned alkylation method, for example, Preparation Example 3 3 (Wherein R1 is 2,4-dichloropyrimidin-5-ylmethyl) is converted to Preparation Example 3 4 (wherein R1 is pyrimidin-5-ylmethyl). Similarly, the amidines of Preparation Examples 102, 103, and 104 and the amidines of Preparation Examples 105, 106, and 107 were prepared from the corresponding Preparation Examples 101 and 69 respectively. In other compounds of the formula (IVA) and (IVB), R1 is C Η 2 H e t can be prepared by the heterocyclic structure after the pyrimilopyrimidone-chemical step. This method is particularly convenient when the required H e t C Η 2 X cannot be obtained. For example, when He t is 3-methyl-1,2,4-triazole-5-yl or 5-methyl-1,2,4-pyridazol-3-yl, Hetero-15- (Please Please read the notes on the back before filling this page) This paper size is applicable to Chinese National Standard (CNS) A4 specification (210X 297mm) 524805 A7 B7 V. Description of the invention (13) Can be made by carboxymethyl precursor or cyanomethyl respectively The radical precursors (that is, compounds of formula (IVA) and formula (JVB) in which R1 is CH2CO2H or CH2CN) are assembled in a series of conventional steps. These methods are described in Preparation Example 6 9 to Preparation Example 7 2 and Preparation Examples 7 3 and 7 7 are converted to Preparation Examples 7 6 and 7 9. Another different way to obtain compounds of formula (IVA) and formula (IVB) is to introduce the R 1 group at an early stage of the synthetic pathway (for example, to produce a N 1-or N 2-appropriately chemicalized pyrawa derivative), Then, formula (IVA) and formula (IV B) are converted in a similar manner to the formula (W) to formula (V) described later. Compounds of formula (V) can be selected from compounds of formula (VI) (please read the notes on the back before filling this page)

(其中R2與R3係如式（V)中所定義者） 經濟部中央標準局員工消費合作社印製 以習知用於形成嘧啶酮環的環化方法製得。 因此舉例而言，其環化可在C: - C4烷醇一水介質中 ，約6 0 t至反應混合物迴流溫度，選擇性有過氧化氫的 情況下以鹼（如氫氧化鈉或氫氧化鉀或碳酸鈉或碳酸鉀） 處理式（V )化合物而達成。 此環化反應也可用C i - C 5烷氧化鈉或烷氧化鉀在 C i - C 5烷醇爲溶劑且溫度在6 0 °C至反應混合物迴流溫 本紙張尺度適用中國國家標準（CNS ) A4規格（210X297公釐）-16 - 524805 Μ ____ Β7 五、發明説明（14 ) 度下協調（mediate)。 另一種環化步驟包括在約1 3 0 °C至約1 5 0 °C下以 多磷酸或在約2 0 0°C至約2 2 〇t下以Lewis酸（如無水 氯化鋅）處理式（V )化合物。 式（VI )化合物可由式（YE )化合物與式（珊）化合 物的選擇性Ν -醯化反應製得：(Where R2 and R3 are as defined in formula (V)) Printed by the Consumer Cooperative of the Central Standards Bureau of the Ministry of Economic Affairs. It is prepared by the conventional cyclization method used to form the pyrimidinone ring. Therefore, for example, the cyclization can be performed in a C: -C4 alkanol monoaqueous medium from about 60 t to the reflux temperature of the reaction mixture, optionally with a base such as sodium hydroxide or hydroxide in the presence of hydrogen peroxide. Potassium or sodium carbonate or potassium carbonate) is achieved by treating a compound of formula (V). This cyclization reaction can also use C i-C 5 sodium alkoxide or potassium alkoxide in C i-C 5 alkanol as the solvent and the temperature at 60 ° C to the reflux temperature of the reaction mixture. This paper applies Chinese national standards (CNS) A4 specifications (210X297 mm) -16-524805 Μ ____ B7 V. Description of invention (14) Mediate. Another cyclization step includes treatment with polyphosphoric acid at about 130 ° C to about 150 ° C or Lewis acid (such as anhydrous zinc chloride) at about 200 ° C to about 220 ° t. Compound of formula (V). Compounds of formula (VI) can be prepared by selective N-fluorination of compounds of formula (YE) and compounds of formula (Shan):

其中R2係如式（VI)中所定義者， (請先閱讀背面之注意事項再填寫本頁)Where R2 is as defined in formula (VI), (please read the precautions on the back before filling this page)

(VIII) 經濟部中央標率局員工消費合作社印製 其中Υ爲適當的離去基’ R3係如式（VI)中所定義者。舉 例而言，當Υ爲氯，則此反應可用適當的芳醯氯在有過量 第三級胺（如三乙胺或吡啶）作爲酸副產物（Η Υ )之淸 除劑，選擇性使用觸媒（如4 一二甲胺基吡啶），於適當 溶劑（如二氯甲烷）中在約〇 t至約室溫下進行。爲方便 起見，亦可以吡啶作爲溶劑。 2 ·式（I A )與（I B )化合物的另一種可利用合 本紙張尺度適用中國國家標準（CNS ) A4規格（210X297公釐） 經濟部中央標率局員工消費合作社印製 524805 A7 B7 五、發明説明（15) 成途徑牽涉到在合成的早期階段將R 4取代基加入。 因此式（I A )或（1 B > {匕合物可分別由式（KA )或（IX B )化合物的環化而製得(VIII) Printed by the Consumer Cooperatives of the Central Bureau of Standards of the Ministry of Economics, where Υ is the appropriate leaving group 'R3 is as defined in formula (VI). For example, when rhenium is chlorine, this reaction can use an appropriate arylene chloride in the presence of an excess of a tertiary amine (such as triethylamine or pyridine) as an acid by-product (Η Υ). Vehicle (such as 4-dimethylaminopyridine), in a suitable solvent (such as dichloromethane) at about 0 to about room temperature. For convenience, pyridine can also be used as a solvent. 2 · Another available compound of formula (IA) and (IB) is available in Chinese paper standard (CNS) A4 specification (210X297 mm) Printed by the Central Consumer Bureau of the Ministry of Economic Affairs Consumer Cooperatives DESCRIPTION OF THE INVENTION (15) The formation pathway involves the addition of the R 4 substituent at an early stage of the synthesis. Therefore, the formula (I A) or (1 B > {dagger compound can be prepared by cyclization of a compound of formula (KA) or (IX B) respectively

其中尺1，112，尺3，尺4係如式（1六）與（18)中所 定義者。此環化反應可在鹼性’中性或酸性條件下進行。 在中性條件下式（K A )或（K B )化合物可在選擇 性使用溶劑及/或脫水劑及/或機械式除水系統（如Dean-Stark 設備） 下加熱 。適 當的 溶劑爲 1 ， 2 —二 氯苯， sulfolane或N —甲基吡咯啶一 2 —酮；適當的脫水劑爲分 子篩；此反應宜在1 8 0至2 2 0 °C下進行。 在酸性條件下，此環化反應可在選擇性使用溶劑的情 況下由式（KA)或（KB)化合物與質子酸或Lewis酸反 應而完成。適當的質子酸爲濃硫酸，磷酸或對甲苯磺酸； 適當的Lewis酸爲三氟化硼，氯化鋁，四氯化矽，氯化錫（ IV )，四氯化鈦，氯化鐵或氯化鋅；適當的溶劑爲冰醋酸 ，四氫呋喃，1，4 一二氧雜環己烷或氯苯。此反應宜在 6 5至2 1 0°C下進行。 不過式（IX A )或（K B )化合物環化反應的較佳模 式是在驗性條件下宜於溶劑裡且選擇性在有過氧化氫或過 本紙張尺度適用中國國家標準（CNS ) A4規格（210X297公釐） (請先閱讀背面之注意事項再填寫本頁)Among them, ruler 1,112, ruler 3, and ruler 4 are as defined in equations (16) and (18). This cyclization reaction can be carried out under basic 'neutral or acidic conditions. Under neutral conditions, compounds of formula (K A) or (K B) can be heated under the optional use of solvents and / or dehydrating agents and / or mechanical water removal systems (such as Dean-Stark equipment). A suitable solvent is 1, 2-dichlorobenzene, sulfolane or N-methylpyrrolidine-2-one; a suitable dehydrating agent is a molecular sieve; this reaction should be carried out at 180 to 220 ° C. Under acidic conditions, this cyclization reaction can be accomplished with the optional use of a solvent by reacting a compound of formula (KA) or (KB) with a protonic or Lewis acid. Suitable protonic acids are concentrated sulfuric acid, phosphoric acid or p-toluenesulfonic acid; suitable Lewis acids are boron trifluoride, aluminum chloride, silicon tetrachloride, tin (IV) chloride, titanium tetrachloride, iron chloride or Zinc chloride; suitable solvents are glacial acetic acid, tetrahydrofuran, 1,4-dioxane or chlorobenzene. This reaction is preferably performed at 65 to 210 ° C. However, the preferred mode of the cyclization reaction of the compound of formula (IX A) or (KB) is that it is suitable in a solvent under test conditions and is selective in the presence of hydrogen peroxide or paper. The Chinese National Standard (CNS) A4 specification is applicable. (210X297 mm) (Please read the notes on the back before filling this page)

524805 A7 B7 五、發明説明（16 ) 氧化物鹽類的情況下進行，必要時再將反應混合物中和。 適當的鹼係選自由鋰，鈉，鉀之Ci-Cia烷氧化物與氫 化物鹽類，胺化鈉（sodannde )，環己基胺化鈉及碳酸鉋 所組成之群組；使用的鹼量爲1·1至2·0莫耳當量； 適當的溶劑係選自乙醇，正丙醇，第三丁醇，第三戊醇， 1 —甲基環己醇，四氫呋喃及1，4 一二氧雜環己烷；此 反應係於6 0至1 0 5 °C進行。 該鹼宜選自乙氧化鈉，第三丁氧化鈉，第三丁氧化鉀 及氫化鈉；該溶劑宜選自乙醇，正丙醇，第三丁醇，第三 戊醇及四氫呋喃。 式（K A )或（K B )化合物可分別由式（X a )或 (X B )化合物 (請先閱讀背面之注意事項再填寫本頁)524805 A7 B7 V. Description of the invention (16) It is carried out in the case of oxide salts, and the reaction mixture is neutralized if necessary. Suitable bases are selected from the group consisting of Ci-Cia alkoxides and hydride salts of lithium, sodium, and potassium, sodium amidate (sodannde), sodium cyclohexyl amine, and carbonate shavings; 1: 1 to 2.0 mole equivalents; suitable solvents are selected from the group consisting of ethanol, n-propanol, third butanol, third pentanol, 1-methylcyclohexanol, tetrahydrofuran and 1,4-dioxane Cyclohexane; this reaction is carried out at 60 to 105 ° C. The base is preferably selected from sodium ethoxide, sodium third butoxide, potassium third butoxide, and sodium hydride; the solvent is preferably selected from ethanol, n-propanol, third butanol, third pentanol, and tetrahydrofuran. Compounds of formula (K A) or (K B) can be composed of compounds of formula (X a) or (X B) respectively (Please read the precautions on the back before filling this page)

(XA) (XB) 經濟部中央標準局員工消費合作社印製 (其中R1與R2係如式（KA)及（KB)所定義者） 與式（X I )化合物 r3o(XA) (XB) Printed by the Consumer Cooperatives of the Central Bureau of Standards of the Ministry of Economic Affairs (where R1 and R2 are as defined by formulas (KA) and (KB))

(XI) 本紙張尺度適用中國國家標準（CNS ) A4規格（210X297公釐）_以 524805 A7 _ B7 五、發明説明（17 ) (其中R3與R4係如式（KA)及（KB)中所定義者） 反應而製成。 (請先閱讀背面之注意事項再填寫本頁) 此耦合反應可利用慣用的醯胺鍵形成技術（例如經由 式（X I )之醯氯衍生物）以類似式（w )化合物的製備 方式達成，確保易反應的取代基（例如當R 1 ◦爲經〇Η或 C ΟΝΗ2取代之C 1— C4院基時）被適當保護。 經濟部中央標準局員工消費合作社印製 更具體而言，可利用各種胺基酸耦合反應之變化，例 如式（X I )酸可用鑛一亞胺如1，3 -二環己基簾二亞 胺或1 一乙基一3 — (3 —二甲胺基丙一1 一基）羰二亞 胺並選擇性有1 -羥苯並三唑及/或觸媒（如4 一二甲胺 基吡啶）的情形下而活化之，或利用一種鹵參胺基鳞鹽如 /、截憐酸漠參（D比略 d定）鳞（bromotris(pyrrolidino) phosphonium hexafluorophosphate)而活化之。不論以何種 耦合方式，均係於適當溶劑（如二氯甲烷）裡並選擇性有 第三級胺（如N -甲基嗎啉或N -乙基二異丙基胺）（例 如當式（X A )或（X B )化合物或該活化試劑係呈酸加 成鹽時）的情況下在大約0 °C之溫度下進行。較佳者係使 用 1 · 1 至 2 · 0 分子當量（molecular equivalents)的活 化試劑及2 · 0至3 . 0分子當量的任何第三級胺。 式（X I )化合物與式（XA)或（XB)化合物之 混合物宜以大約1分子當量耦合試劑六氟磷酸（苯並三唑 一 1 一基氧）三吡咯啶鱗（PyBOP)於適當溶劑如二 甲基甲醯胺裡在大約室溫下加以處理。 在另一種變化方式中，式（X I )羧酸可先以約5% 本紙張尺度適用中國國家標準（CNS ) A4規格（210X297公釐）-2〇 · 524805 A7 _____ B7 五、發明説明（20) 體內活性 利用 Trigo-Rocha 等人（Neurourol. and Urodyn·，1994, IL 7 1 )所述方法令化合物於已麻醉的狗體內進行檢測（ screen )’以測定這些化合物在靜脈注射（i · v ·)投與 後提局陰巫海綿體內因海綿體內注射（i n t r a c a v e r η 〇 s a 1 injection)硝普鈉所引發壓力上升的能力。 經濟部中央標準局員工消費合作社印製 (請先閱讀背面之注意事項再填寫本頁) 當用於治療人類時式（I A)與（I B)化合物，其 藥學上可接受鹽，及其藥學上可接受之溶劑合物可單獨施 用，但一般係與藥學載體（依所要的施藥途徑及標準藥學 實務加以選擇）混合施用。其宜以含有諸如澱粉或乳糖之 賦形劑而呈錠劑形態；或單獨或連同賦形劑而呈膠囊或卵 囊形態；或含有調味劑或著色劑而呈酏劑（elixirs )，溶 液或懸浮液之形態口服。其亦可以非經腸方式注射，例如 海綿體內注射，靜脈內注射，肌內注射或皮下注射。於非 經腸給藥之用時，則最好以無菌水溶液形態投與，且該溶 液含有其他物質如足夠的鹽或單醣以使該溶液與血液等張 。若於頰或舌下給藥之用時，則可以慣用方式配成的錠劑 (tablets or logenges )投與。 於病患口服，非經腸，頰內與舌下方式給藥時，式（ I A )與（I B )化合物及其藥學上可接受鹽和溶劑合物 的每日服用量可爲10至50 Omg (單一劑量或分次劑 量）。故舉例而言，錠劑或膠囊可含5至lOOmg有效 化合物以供一次投與一份，二份或以上。醫師會依各個病 本紙張尺度適用中國國家標準（CNS ) A4規格（210Χ 297^釐） ~ 524805 經濟部中央標準局員工消費合作社印製 A7 B7 五、發明説明（24) 效治療量的式（I A )或（I B )之化合物，或其藥學上 或獸醫學上可接受之鹽類，或其藥學上或獸醫學上可接受 之溶劑合物，或含有前述任一物質之藥學組合物或獸醫調 配物。 本發明還包括文中所述任何新穎之中間物’如式（ Π A ) ，（ΠΒ) ，( IV A ) ，( IV B ) ，（KB)及（ IX B )者。 本發明化合物之合成及用於該合成之中間物透過以下 之實施例與製備例加以說明。 1 Η核磁共振（N M R )光譜係利用Vanan Unity 300 或Varian Inova 400光譜儀測錄，結果均與所提出之結構相 符。至於特性化學位移（5 )係以每百萬份中之份數自四 甲基矽烷向低場區計算並利用慣用縮寫以指定主峰，例如 s表單峰，d表雙重峰，t表三重峰，Q表四重峰，m表 多重峰，b爲寬幅峰。 質譜（m/z )係以 Fisons Instruments Trio 質譜儀以 熱噴霧離子化模式（thermospray ionisation mode )測得。 室溫表示2 0至2 5°C。 實施例1 1 / 2 -經烷基化_ 5 — ( 2 —烷氧苯基）—3 -烷 基一1/2，6 — 二氫—7H -批哩並〔4，3 — d〕！P密 啶- 7 -酮類的胺基磺醯化 把氯磺酸（3 0 m m ο 1 )慢慢加入以冰冷卻之N 1 本紙張尺度適用中國國家標準（CNS ) A4規格（210X297公釐）-27 - t------、玎------· (請先閱讀背面之注意事項再填寫本頁) 524805 A7 B7 五、發明説明（25) 一或N2 -經院基化的受質（3mmo 1 )試樣裡，然後 添加硫醯氯（4 · 5 m m ο 1 )，接著令混合物升溫至室 溫，並攪拌2 4小時。反應混合物以冰冷卻，小心把混合 物倒入攪拌的冰/水裡，隨後收集沈澱物並以抽氣方式乾 燥而得到純度足以直接用於後續N -磺醯化步驟的粗製磺 醯氯。 將過量（大體上爲2 — 5莫耳當量）1 一取代的六氫 吡畊分批加入由磺醯氯及乙醇所形成的攪拌混合物裡，令 反應混合物於室溫下攪拌2 0小時，然後減壓蒸發。令殘 餘物在乙酸乙酯和飽和碳氫酸鈉水溶液之間分配（partition )，有機相的部份分離出來後與由乙酸乙酯對水相萃取三 次所得乙酸乙酯萃取液合倂之後，將此合倂的有機溶液加 以乾燥（N a 2 S〇4 )並減壓蒸發而得到粗製的磺醯胺， 此磺醯胺再經管柱層析方式在矽膠上加以純化。 如果磺醯氯在以冰-水中止該氯磺酸化反應混合物時 並未沈澱出來，則用等體積乙醇稀釋所得水溶液，再經冰 的冷卻，並用前述的適當六氫吡畊衍生物處理之。 經濟部中央標準局員工消費合作社印製 (讀先閱讀背面之注意事項再填寫本頁) 實施例2 3 —乙基一 5 —〔5 —（4 —乙基六氫吡畊一1 一基 磺醯基）一 2 —正丙氧苯基〕—1 一（吡啶一 2 —基）甲 基—1，6 —二氫一 7H —吡唑並〔4，3 — d〕嘧啶一 7 -酮 由製備例1 6的標題化合物及1 一乙基六氫吡畊利用 本紙張尺度適用中國國家標準（CNS ) A4規格（210X297公釐）-28 - 524805 A7 B7 五、發明説明（26) 實施例1之步驟製得，呈白色固體（40%)。元素分析 實測値 C : 5 9 · 0 6 ，Η : 6 · 1 9 ，N : 1 7 ·〇〇 ，而 C28H35N7〇4S 計算値爲 C : 59.45 ，Η : 6.24 ;Ν: 17.33%。 5(CDCl3) :1.02(3H，t)， 1 · 1 8 ( 3 Η，t )， 1 · 4 2 ( 3 Η，t )， 2 · 0 2 ( 2 Η，m )， 2 · 4 〇（2 Η，Q )， 2 · 5 4 ( 4 Η，m )， 3 ·〇 2 ( 2 Η，Q )， 3 · 1 2 ( 4 Η，m )， 4 · 2 5 ( 2 Η，t )， 5 · 9 3 ( 2 Η，. s )， 7 · 0 0 ( 1 Η，d )， 7 · 1 7 ( 2 Η，m )， 7 · 6 0 ( 1 Η，m )， 經濟部中央標準局員工消費合作社印製 (請先閱讀背面之注意事項再填寫本頁) 7 · 8 4 ( 1 Η，d )， 8 · 5 8 ( 1 Η，d )， 8 · 8 8 ( 1 Η，s )， 10.92(lH，s) ° LRMS:m/z 566 (M+1)+。 實施例3 本紙張尺度適用中國國家標準（CNS ) A4規格（21〇X 297公釐） -29- 524805 A7 B7 五、發明説明（27 ) 經濟部中央標準局員工消費合作社印1i 5 — ( 5 — ( 4 — 甲基六 氫 吡畊 一 I — 基 磺 醯 基 ) — 2 — 正 丙 氧 苯 基 ) — 3 一正丙 基 -I — ( 吡 π定 — 2 — 基 ) 甲 基 — I 6 — 二 氫 — 7 Η - 吡 唑並 [ 4 y 3 — d ] 嘧 U定 — 7 — 酮 由 製 備 例 I 7 之 標 題化合 物 及I — 甲 基 _户· 氫 吡 畊依 實 施 例 I 之 步 驟 製 得 呈 白色固 體 (6 2 % ) 〇 元 素 分析 實 測 値 ·· C 5 9 . 5 I ； Η ， 6 • 4 2 ， N I 6 • 6 7 〇 C 2 Ε 丨Η 3 5 Ν 7〇 4 S計 算 値 C 5 9 • 4 5 Η j 6 . 2 4 ；N 5 I 7 • 3 3 % 〇 5 ( C D C I 3 : ) l .02 (, 3 Η 5 t ) ， I • I 8 ( 3 Η ， t ) 5 I • 4 2 ( 3 Η ， t ) ? 2 • 0 2 ( 2 Η 5 m ) y 2 參 4 0 ( 2 Η ，· Q ) 5 2 • 5 4 ( 4 Η m ) ， 3 參 〇 2 ( 2 Η ， Q ) 3 • I 2 ( 4 Η > m ) j 4 • 2 5 ( 2 Η ， t ) j 5 • 9 3 ( 2 Η ， s ) 5 7 • 〇 0 ( I Η 5 d ) ? 7 • I 7 ( 2 Η y m ) 5 7 • 6 〇 ( I Η y m ) > 7 • 8 4 ( I Η j d ) 8 5 8 ( I Η d ) ， 本紙張尺度適用中國國家標準（CNS ) A4規格（210X297公釐） -30- (讀先閱讀背面之注意事項再填寫本頁) 524805 A7 B7 五、發明説明（28 ) 8 · 8 8 ( 1 Η，s )， 10.92(lH，s)。 LRMS:m/z 566 (M+1)+。 實施例4 5 — {5 —〔4 一（2 —羥乙基）六氫吡哄一1 一基 磺醯基〕2 -正丙氧苯基} 一 3 —正丙基一 1 一（吡啶一 2 —基）甲基一 1 ，6 —二氫一7H —吡唑並〔4，3 — d〕嘧啶一 7 —酮 由製備例17之標題化合物及1一（2—羥乙基）六 氫吡畊依實施例1之步驟製得，呈白色泡沬（foam )狀（ 12%)。 元素分析實測値：C，5 8 · 1 8 ; Η，6 · 2 5 ; N， 15.81°C2,9H37N7〇5S 計算値 C，58 ·47;Η，6·26;Ν，16.46%。 5 ( C D C 1 3 ) :1.00(3H，t)， 1 · 1 8 ( 3 H，. t )， 經濟部中央標準局員工消費合作社印製 (請先閱讀背面之注意事項再填寫本頁) 1 · 8 8 ( 2 H，m )， 2 · 0 4 ( 2 H，m )， 2 · 3 0 ( 1 H，s )， 2 · 5 8 ( 2 H，m )， 2 · 6 6 ( 4 H，m )， 2 · 9 8 ( 2 H，t )， 3 · 1 3 ( 4 H，m )， 本紙張尺度適用中國國家標準（CNS ) A4規格（210X297公釐） -31 - 524805 A7 B7 經濟部中央標準局員工消費合作社印製 五、發明説明（29) 3 . 5 8 ( 2 Η，t )， 4 . 2 8 ( 2 Η，t )， 5 · 9 6 ( 2 Η，s )， 7 ·〇〇（1 Η ， d )， 7 · 1 8 ( 2 Η，m )， 7 · 6 Ο ( 1 Η，m )， 7 · 8 6 ( 1 Η，d )， 8 . 5 8 ( 1 Η，d )， 8 · 9 〇（1 Η，s )， 1 Ο · 9 4 ( 1 Η，s )。 LRMS:m/z 5 96 (Μ+1)+。 實施例5 A 3 —乙基一5 —〔5 — (4 —乙基六氫吡畊一 1 一基 磺醯基）一 2 —正丙氧苯基〕一 2 —（吡啶一 2 —基）曱 基—2，6 —二氫—7H —吡唑並〔4，3 — d〕嘧啶― 7 —酮 (a )由製備例1 8之標題化合物及1 一乙基六氫吡 畊依實施例1之步驟製得，呈白色固體（3 0 % )。 元素分析實測値：C，5 8 · 9 2 ; Η，6 · 3 4 ; N， 17 · 03。C28H35N7〇4S 計算値 C，59.45;H，6.24;N，17.33%。 (5(CDCl3):1.02(3H，t)， 1 · 1 4 ( 3 Η ， t )， (請先閲讀背面之注意事項再填寫本頁) 本紙張尺度適用中國國家標準（CNS ) A4規格（210X 297公釐） _ 32 - 524805 經濟部中央標準局員工消費合作社印製 A7 B7 五、發明説明（30) 1 · 3 〇 ( 3 Η，t )， 2 · 0 2 ( 2 Η ’ m )， 2 · 4 〇 ( 2 Η，Q )， 2 · 5 2 ( 4 Η，m )， 3 · 〇 4 ( 2 Η，Q )， 3 · 〇 8 ( 4 Η，m )， 4 · 2 3 ( 2 Η，t )， 5 · 6 8 ( 2 Η，s )， 7 · 0 8 ( 1 Η，d )， 7 · 1 5 ( 1 Η，d )， 7.2〇(lH，m)， 7 · 6 2 ( 1 H，m )， 7 · 8 2 ( 1 H，d )， 8 · 5 8 ( 1 H ; d )， 8 · 7 8 ( 1 H，s )， 10.6 0(1H，s)。 L R M S · m / z 566 (M+l)+。 (b)將製備例136的標題化合物（385·lg ，0 · 66mmo 1)及正丙醇（1932ml)的攪拌 混合物減壓蒸餾至去除半量體積（9 9 〇m 1 )的正丙醇 ，然後在氮氣下冷卻至大約3 。在1 5分鐘的期間分 批添加第三丁氧化鉀（222 · 2g，1 . 98mo 1) ，再於迴流狀態下加熱該反應混合物2 6小時，接著冷卻 (請先閱讀背面之注意事項再填寫本頁}(XI) This paper size applies Chinese National Standard (CNS) A4 specification (210X297 mm) _ 524805 A7 _ B7 V. Description of the invention (17) (where R3 and R4 are as shown in formulas (KA) and (KB) Definer). (Please read the notes on the back before filling out this page) This coupling reaction can be achieved in a similar manner to the compound of formula (w) by using the conventional amide bond formation technology (for example, via the fluorene chloride derivative of formula (XI)). Ensure that the easily reactive substituents (for example, when R 1 is a C 1-C 4 radical substituted with 〇Η or CO ON 2) are properly protected. Printed by the Consumer Cooperative of the Central Bureau of Standards of the Ministry of Economic Affairs. More specifically, various amino acid coupling reactions can be used. For example, an acid of formula (XI) can be used as an amine-imine such as 1,3-dicyclohexyl curtain diimide or 1-Ethyl 3- (3-dimethylaminopropyl-1 1-yl) carbodiimide and optionally 1-hydroxybenzotriazole and / or catalyst (eg 4-dimethylaminopyridine) It can be activated under certain conditions, or it can be activated with a halogenated amine scale salt, such as bromotris (pyrrolidino) phosphonium hexafluorophosphate. Regardless of the coupling method, it is in a suitable solvent (such as dichloromethane) and optionally has a tertiary amine (such as N-methylmorpholine or N-ethyldiisopropylamine) (for example, when the formula When the (XA) or (XB) compound or the activating reagent is an acid addition salt), the reaction is performed at a temperature of about 0 ° C. The preferred one is the use of 1 · 1 to 2 · 0 molecular equivalents of activating reagent and 2 · 0 to 3.0 molecular equivalents of any tertiary amine. A mixture of a compound of formula (XI) and a compound of formula (XA) or (XB) is preferably coupled to the reagent hexafluorophosphate (benzotriazole-1 1-oxy) tripyrrolidine scale (PyBOP) in an appropriate solvent such as about 1 molecular equivalent. The dimethylformamide is processed at about room temperature. In another variation, the carboxylic acid of formula (XI) may first be applied to the Chinese National Standard (CNS) A4 specification (210X297 mm) at a paper size of approximately 5%. -2 · 524805 A7 _____ B7 V. Description of the invention (20 ) In vivo activity Using the method described by Trigo-Rocha et al. (Neurourol. And Urodyn., 1994, IL 71), the compounds were tested in anesthetized dogs (screen) 'to determine whether these compounds were injected intravenously (i.v. ·) The ability to raise pressure after intracorporeal intracavernosine injection (sodium nitrate sodium injection) after intracorporeal injection. Printed by the Consumer Cooperative of the Central Standards Bureau of the Ministry of Economic Affairs (please read the precautions on the back before filling this page). When used in the treatment of humans, the compounds of formula (IA) and (IB), their pharmaceutically acceptable salts, and their pharmacologically acceptable Acceptable solvates can be administered alone, but generally are mixed with a pharmaceutical carrier (selected according to the desired route of administration and standard pharmaceutical practice). It is preferably in the form of lozenges containing excipients such as starch or lactose; or in the form of capsules or oocysts alone or in combination with excipients; or in the form of elixirs, solutions or containing flavouring or coloring agents The suspension is administered orally. It can also be injected parenterally, such as intracavernosal injection, intravenous injection, intramuscular injection or subcutaneous injection. For parenteral administration, it is best to administer as a sterile aqueous solution, and the solution contains other substances such as sufficient salts or monosaccharides to make the solution isotonic with blood. If it is used for buccal or sublingual administration, it can be administered in tablets or logenges prepared in a conventional manner. For oral, parenteral, buccal and sublingual administration of the patient, the daily dosage of the compounds of formula (IA) and (IB) and their pharmaceutically acceptable salts and solvates may be 10 to 50 Omg (Single or divided doses). Thus, for example, tablets or capsules may contain 5 to 100 mg of the effective compound for administration in one, two or more portions at a time. Physicians will apply Chinese National Standard (CNS) A4 specifications (210 × 297 ^^) to 524805 according to the paper size of each disease paper. A7 B7 printed by the Consumer Cooperatives of the Central Standards Bureau of the Ministry of Economic Affairs. IA) or (IB) compounds, or pharmaceutically or veterinarily acceptable salts thereof, or pharmaceutically or veterinarily acceptable solvates thereof, or pharmaceutical compositions or veterinary medicines containing any of the foregoing Preparations. The present invention also includes any of the novel intermediates described in the text, such as the formulae (ΠA), (ΠB), (IVA), (IVB), (KB), and (IXB). The synthesis of the compound of the present invention and the intermediates used in the synthesis will be explained through the following examples and preparation examples. 1 Erbium nuclear magnetic resonance (N M R) spectroscopy was recorded with a Vanan Unity 300 or Varian Inova 400 spectrometer, and the results are consistent with the proposed structure. As for the characteristic chemical shift (5), calculated in parts per million from tetramethylsilane to the low field region and using conventional abbreviations to specify the main peaks, such as s-form peaks, d-table double peaks, t-table triplet peaks Q indicates a quartet, m indicates a multiplet, and b indicates a broad peak. Mass spectrum (m / z) was measured with a Fisons Instruments Trio mass spectrometer in a thermospray ionisation mode. Room temperature means 20 to 25 ° C. Example 1 1/2-Alkylated _ 5-(2 -alkoxyphenyl)-3 -alkyl-1/2, 6-dihydro-7H-pyrido [4,3 — d]! Pamidine-7-ketone amine sulfonation Slowly add chlorosulfonic acid (30 mm ο 1) to ice-cooled N 1 This paper is sized to the Chinese National Standard (CNS) A4 (210X297 mm) ) -27-t ------, 玎 ------ · (Please read the notes on the back before filling this page) 524805 A7 B7 V. Description of the invention (25) One or N2-by the foundation Into the sample (3mmo 1), then add thionine chloride (4.5 mm ο 1), then allow the mixture to warm to room temperature and stir for 24 hours. The reaction mixture was ice-cooled, and the mixture was carefully poured into stirred ice / water, and then the precipitate was collected and dried under suction to obtain crude sulfonium chloride which was pure enough to be used directly in the subsequent N-sulfonation step. The excess (generally 2-5 mol equivalents) of 1-substituted hexahydropyrine was added in portions to a stirred mixture of sulfonium chloride and ethanol, and the reaction mixture was stirred at room temperature for 20 hours, and then Evaporate under reduced pressure. The residue was partitioned between ethyl acetate and a saturated aqueous solution of sodium bicarbonate. The organic phase was separated and the ethyl acetate extract was extracted three times with ethyl acetate and the aqueous phase was combined. The combined organic solution was dried (N a 2 S04) and evaporated under reduced pressure to obtain the crude sulfonamide. The sulfonamide was purified on silica gel by column chromatography. If the sulfonyl chloride did not precipitate when the chlorosulfonation reaction mixture was quenched with ice-water, the resulting aqueous solution was diluted with an equal volume of ethanol, cooled with ice, and treated with the appropriate hexahydropyrine derivative as described above. Printed by the Consumer Cooperatives of the Central Bureau of Standards of the Ministry of Economic Affairs (Read the precautions on the back before filling this page) Example 2 3 —Ethyl-5 — [5 — (4 —Ethylhexahydropyridine-1 1-Sulfur Fluorenyl)-2 -n-propoxyphenyl]-1-(pyridine-2 -yl) methyl-1, 6-dihydro-7H-pyrazolo [4,3 — d] pyrimidine-7 -one by Preparation Example 16 The title compound of 6 and 1-ethylhexahydropyridine are used in this paper. The size of the paper is applicable to the Chinese National Standard (CNS) A4 (210X297 mm) -28-524805 A7 B7 V. Description of the Invention (26) Example 1 Obtained as a white solid (40%). Elemental analysis Measured 値 C: 59 · 06, Η: 6 · 19, N: 17 · 〇〇, and C28H35N7044S calculated 値 as C: 59.45, Η: 6.24; N: 17.33%. 5 (CDCl3): 1.02 (3H, t), 1 · 1 8 (3 Η, t), 1 · 4 2 (3 Η, t), 2 · 0 2 (2 Η, m), 2 · 4 〇 ( 2 Η, Q), 2 · 5 4 (4 Η, m), 3 · 〇 2 (2 Η, Q), 3 · 1 2 (4 Η, m), 4 · 2 5 (2 Η, t), 5 · 9 3 (2 Η,. S), 7 · 0 0 (1 Η, d), 7 · 1 7 (2 Η, m), 7 · 6 0 (1 Η, m), Central Bureau of Standards, Ministry of Economic Affairs Printed by the employee consumer cooperative (please read the notes on the back before filling out this page) 7 · 8 4 (1 Η, d), 8 · 5 8 (1 Η, d), 8 · 8 8 (1 Η, s) , 10.92 (lH, s) ° LRMS: m / z 566 (M + 1) +. Example 3 This paper size applies the Chinese National Standard (CNS) A4 specification (21 × 297 mm) -29- 524805 A7 B7 V. Description of the invention (27) Employees' Cooperatives of the Central Standards Bureau of the Ministry of Economic Affairs printed 1i 5 — (5 — (4 —methylhexahydropyridine—I —sulfosulfanyl) — 2 —n-propoxyphenyl) — 3 —n-propyl-I — (pyridine — 2 —yl) methyl — I 6 — Dihydro— 7 pyrene-pyrazolo [4 y 3 — d] Pyrididine-7-one was prepared from the title compound of Preparation Example 7 and I-methyl_household hydropyridine according to the procedure of Example I Obtained as a white solid (62%). Measured by elemental analysis 値 ·· C 5 9. 5 I; Η, 6 • 4 2, NI 6 • 6 7 〇C 2 Ε Η 5 3 5 Ν 〇 4 S calculation 値C 5 9 • 4 5 Η j 6. 2 4; N 5 I 7 • 3 3% 〇5 (CDCI 3:) l .02 (, 3 Η 5 t), I • I 8 (3 Η, t) 5 I • 4 2 (3 Η, t)? 2 • 0 2 (2 Η 5 m) y 2 See 4 0 (2 ，, · Q) 5 2 • 5 4 (4 Η m), 3 ref. 〇2 (2 Η, Q) 3 • I 2 (4 Η > m) j 4 • 2 5 (2 Η, t) j 5 • 9 3 (2 Η, s) 5 7 • 〇0 (I Η 5 d)? 7 • I 7 (2 Η ym) 5 7 • 6 〇 (I Η ym) > 7 • 8 4 (I Η jd) 8 5 8 ( I Η d), this paper size applies to Chinese National Standard (CNS) A4 specification (210X297 mm) -30- (Read the precautions on the back before filling this page) 524805 A7 B7 V. Description of the invention (28) 8 · 8 8 (1 Η, s), 10.92 (lH, s). LRMS: m / z 566 (M + 1) +. Example 4 5 — {5 — [4-((2-hydroxyethyl) hexahydropyridine-1—1-sulfofluorenyl] 2-n-propoxyphenyl}} 3—n-propyl-1 1— (pyridine— 2-Methyl) methyl-1,6-dihydro-7H-pyrazolo [4,3-d] pyrimidin-7-one was prepared from the title compound of Preparation 17 and 1- (2-hydroxyethyl) hexahydro Pycnogenol was prepared according to the procedure of Example 1 and was white foam (12%). Elemental analysis: 値: C, 5 8 · 18; Η, 6 · 2 5; N, 15.81 ° C2, 9H37N7〇5S Calculate 値 C, 58 · 47; Η, 6.26; N, 16.46%. 5 (CDC 1 3): 1.00 (3H, t), 1 · 1 8 (3 H,. T), printed by the Consumer Cooperatives of the Central Standards Bureau of the Ministry of Economic Affairs (please read the precautions on the back before filling out this page) 1 · 8 8 (2 H, m), 2 · 0 4 (2 H, m), 2 · 3 0 (1 H, s), 2 · 5 8 (2 H, m), 2 · 6 6 (4 H , M), 2 · 9 8 (2 H, t), 3 · 1 3 (4 H, m), this paper size applies to China National Standard (CNS) A4 (210X297 mm) -31-524805 A7 B7 Economy Printed by the Consumer Cooperatives of the Ministry of Standards of the People's Republic of China. 5. Description of Invention (29) 3. 5 8 (2 Η, t), 4. 2 8 (2 Η, t), 5 · 9 6 (2 Η, s), 7 · 〇〇 (1 Η, d), 7 · 1 8 (2 Η, m), 7 · 6 〇 (1 Η, m), 7 · 8 6 (1 Η, d), 8. 5 8 (1 Η , D), 8 · 9 0 (1 Η, s), 1 0 · 9 4 (1 Η, s). LRMS: m / z 5 96 (M + 1) +. Example 5 A 3 -Ethyl-5-[5-(4-Ethylhexahydropyridine) 1 -N-propoxyphenyl] -2-(Pyridin-2-yl) Amidino-2,6-dihydro-7H-pyrazolo [4,3-d] pyrimidin-7-one (a) was prepared from the title compound of Preparation Example 18 and 1-ethylhexahydropyridine Example Obtained in step 1 as a white solid (30%). Elemental analysis: 値: C, 5 8 · 9 2; Η, 6 · 3 4; N, 17 · 03. C28H35N704. Calculated 値 C, 59.45; H, 6.24; N, 17.33%. (5 (CDCl3): 1.02 (3H, t), 1 · 1 4 (3 Η, t), (Please read the precautions on the back before filling out this page) This paper size applies the Chinese National Standard (CNS) A4 specification ( 210X 297 mm) _ 32-524805 A7 B7 printed by the Consumer Cooperatives of the Central Standards Bureau of the Ministry of Economic Affairs 5. Description of the invention (30) 1 · 3 〇 (3 Η, t), 2 · 0 2 (2 Η 'm), 2 · 4 0 (2 Η, Q), 2 · 5 2 (4 Η, m), 3 · 〇 4 (2 Η, Q), 3 · 〇 8 (4 Η, m), 4 · 2 3 (2 Η, t), 5 · 6 8 (2 Η, s), 7 · 0 8 (1 Η, d), 7 · 1 5 (1 Η, d), 7.2〇 (lH, m), 7 · 6 2 (1 H, m), 7 · 8 2 (1 H, d), 8 · 5 8 (1 H; d), 8 · 7 8 (1 H, s), 10.6 0 (1H, s). LRMS · m / z 566 (M + 1) +. (b) A stirred mixture of the title compound (385 · lg, 0.666mmo 1) and n-propanol (1932ml) of Preparation Example 136 was distilled under reduced pressure to remove half volume (9 90 mM 1) of n-propanol, and then cooled to about 3 under nitrogen. The third potassium butoxide (222 · 2g, 1.98mo 1) was added in portions over a period of 15 minutes, and then returned to Mixture was state 6 hours the reaction was heated, then cooled (Read Notes on the back page and then fill}

本紙張尺度適用中國國家標準（CNS ) A4規格（210X297公釐） -33- 524805 A7 B7 五、發明説明（31) ，以水（1 9 3 2 m 1 )處理，並加以過濾，以1 Μ氫氯 酸（ 1 8 4 〇 m 1 ) 調整濾液之分子量至7 · 5，然後令 固體沈澱物進行 3〇分鐘的造粒，經收集後以水洗之並乾 燥而得到呈白 7 3.7%) 色固體之標題化合物（275 . 2g， ο δ ( D Μ S 〇 d 6 ) :〇.92X6H，m)， 1 . 1 9 ( 3 Η ，t )， 1 . 7 2 ( 2 Η ，m )， 2 . 2 5 ( 2 Η ，Q )， 2 . 3 9 ( 4 Η ，m )， 2 · 8 8 ( 4 Η ，m )， 2 · 9 6 ( 2 Η ，Q )， 4 · 1 1 ( 2 Η ，t )， 5 . 6 8 ( 2 Η ，· s )， 7 . 2 1 ( 1 Η ，d )， 7 · 3 4 ( 3 Η ，m )， 7 . 8 〇 ( 2 Η ，m )， 7 · 8 7 ( 1 Η J s )， 8 . 5 1 ( 1 Η ，d )， 經濟部中央標準局員工消費合作社印製 (讀先閱讀背面之注意事項再填寫本頁) 11.72(lH，s)。 LRMS:m/z 566 (M+1)+。This paper size applies the Chinese National Standard (CNS) A4 specification (210X297 mm) -33- 524805 A7 B7 V. Description of the invention (31), treated with water (193 2 m 1), and filtered to 1 Μ Hydrochloric acid (1840m 1) Adjust the molecular weight of the filtrate to 7.5, and then granulate the solid precipitate for 30 minutes. After collecting, wash with water and dry to obtain white 7.3.7%). The title compound as a solid (275. 2 g, ?? (D M S 0d 6): 0.92 X 6 H, m), 1. 19 (3 Η, t), 1. 7 2 (2 ，, m), 2 2 5 (2 Η, Q), 2. 3 9 (4 Η, m), 2 · 8 8 (4 Η, m), 2 · 9 6 (2 Η, Q), 4 · 1 1 (2 Η , T), 5. 6 8 (2 Η, · s), 7. 2 1 (1 Η, d), 7 · 3 4 (3 Η, m), 7.8 (2 Η, m), 7 · 8 7 (1 Η J s), 8. 5 1 (1 Η, d), printed by the Consumer Cooperatives of the Central Standards Bureau of the Ministry of Economic Affairs (read the precautions on the back before filling out this page) 11.72 (lH, s) . LRMS: m / z 566 (M + 1) +.

實施例5 B 3 —乙基一 5 —〔5 — (4_乙基六氫吡畊一1—基 木紙張尺度適$中國國家標準（CNS ) A4規格（210X297公釐） 524805 A7 B7 五、發明説明（32) 磺醯基）2 -正丙氧苯基〕一 2 -（吡啶一 2 —基）甲基 —2，6 二氫—7H — 吡唑並〔4 ’ 3 — d〕嘧啶一 7 — 酮檸檬酸鹽 將實施例5 A之標題化合物（1 5 · 0 g ’ 26 · 5mmo 1 )與丙酮（1 50ml )之攪拌混合物 在迴流下加熱，然後過濾之。接著把經過過濾的檸檬酸（ 5.1〇g，26.5mmol)(置於丙酮（75ml )及水（7 · 5 m 1 )之混合物裡）溶液加入該攪拌的濾 液裡，然後迴流加熱反應混合物7 5分鐘後令其冷卻。對 生成的懸浮液進行粒化1小時並過濾，得到的固體以丙酮 (2 0 m 1 )洗，再於4 5 °C乾燥之而得到呈白色固體之 標題化合物（18 · 33g ’ 91%)。 m · ρ · 1 8 5 °C。元素分析實測値：C，5 3 · 8 4 ; H’ 5 · 71 ;N，12 · 89 °C28H35N7〇4S ; C6H8〇7 計算値 c，53 · 89 ;H，5· 72 ;N， 12.94。 5 ( D M S 0 d 6 ) :0.95 (6H，m)， 經濟部中央標準局員工消費合作社印製 1 · 2 0 ( 3 h，t )， 1 · 7 2 ( 2 H，m )， 2·40 〜2.73(10H，m)， 2.96 (4H，m)， 4 · 1 1 ( 2 H，t )， 5 · 6 8 ( 2 H，s )， 7 · 2 1 ( i h，d )， -35- (請先閱讀背面之注意事項再填寫本頁) 本紙張尺度適用中國國家標準（CNS ) A4規格（210X297公釐） 524805 A7 B7 五、發明説明（33) 7 · 3 4 ( 2 Η，m )， 7 · 8 2 ( 3 Η，m )， 8 · 5 1 ( 1 Η，d )， 1 1 · 7 2 ( 1 Η，s ) 實施例 一正 -2 一酮 施例 元素 17 ；Η 5 ( 5 -〔5- (4-甲基六氫吡啡一 1-基磺酸基）2 丙氧苯基〕一 3 —丙基一 2 —(吡啶一 2 —基）甲基 ，6 -二氫—7Η — π比哗並〔4，3 - d〕嚼陡一 7 由製備例2 0之標題化合物及1 -甲基六氫吡啡依實 1之步驟製得，呈白色固體（53%)。 分析實測値：C，5 8 · 9 6 ; Η，6 . 2 3 ; N， • 03。C28H35N7〇4S 計算値 C，5 9 · 45 ，6·24;Ν，17.33%. C D C 1 a ) :0.96(3H，t)， 1 6 ( 3 Η (請先閱讀背面之注意事項再填寫本頁) 經濟部中央標準局員工消費合作社印製Example 5 B 3 —Ethyl-5 — [5 — (4-Ethylhexahydropyridine 1—Base wood paper is suitable for Chinese National Standard (CNS) A4 specifications (210X297 mm) 524805 A7 B7 V. Description of the Invention (32) Sulfonyl) 2 -n-propoxyphenyl]-2-(pyridine 2 -yl) methyl-2, 6 dihydro-7H-pyrazolo [4 '3 — d] pyrimidine- 7-Ketocitrate The stirred mixture of the title compound of Example 5A (15. 0 g '26. 5 mmo 1) and acetone (150 ml) was heated under reflux and then filtered. Next, a filtered solution of citric acid (5.10 g, 26.5 mmol) (in a mixture of acetone (75 ml) and water (7.5 m 1)) was added to the stirred filtrate, and the reaction mixture was heated at reflux 7 5 Let it cool after a few minutes. The resulting suspension was granulated for 1 hour and filtered. The resulting solid was washed with acetone (20 m 1) and dried at 45 ° C to give the title compound as a white solid (18.33 g '91%) . m · ρ · 1 8 5 ° C. Elemental analysis: 値: C, 5 3 · 8 4; H '5 · 71; N, 12 · 89 ° C28H35N7〇4S; C6H8 07 Calculate 値 c, 53 · 89; H, 5.72; N, 12.94. 5 (DMS 0 d 6): 0.95 (6H, m), printed by the Consumer Cooperatives of the Central Standards Bureau of the Ministry of Economic Affairs 1 · 2 0 (3 h, t), 1 · 7 2 (2 H, m), 2.40 ~ 2.73 (10H, m), 2.96 (4H, m), 4 · 1 1 (2 H, t), 5 · 6 8 (2 H, s), 7 · 2 1 (ih, d), -35- (Please read the precautions on the back before filling this page) This paper size is applicable to the Chinese National Standard (CNS) A4 specification (210X297 mm) 524805 A7 B7 V. Description of the invention (33) 7 · 3 4 (2 Η, m) , 7 · 8 2 (3 Η, m), 8 · 5 1 (1 Η, d), 1 1 · 7 2 (1 Η, s) Example 1 n-2 monoketone Example Element 17; Η 5 ( 5-[5- (4-methylhexahydropyridine-l-ylsulfonyl) 2 propoxyphenyl] -3-propyl-2- (pyridine-2-yl) methyl, 6-dihydro —7Η — π Biwa and [4,3-d] chewing steep 7 Prepared from the title compound of Preparation Example 2 and 1-methylhexahydropyridine according to the procedure of Ishta 1, as a white solid (53%) Analyzed and measured 値: C, 5 8 · 9 6; Η, 6. 2 3; N, • 03. C28H35N7〇4S Calculate 値 C, 5 9 · 45, 6. 24; N, 17.33%. CDC 1 a) : 0.96 (3H, t), 1 6 (3 Η (Please read the notes on the back before filling out this page) Printed by the Staff Consumer Cooperative of the Central Standards Bureau of the Ministry of Economic Affairs

Ji THX Ji TT- Ji THX THX ΤΓ* Li ΤΓ Li Li LI Li 2 2 3 4 2 4 2 Γν κ(\ /IV xiv /IV /{V 6 4 6 0 8 0 5 7 0 2 5 9 1 2 1 2 2 2 2 3 4 x)y \ly 1/ m m s m t m t -36- 本紙張尺度適用中國國家標準（CNS ) A4規格（21〇X 297公釐） 524805 A7 B7 五、發明説明（34) 5 · 6 6 ( 2 Η，s )， 7 . 0 6 ( 1 Η，d )， 7 · 1 5 ( 1 Η，d )， 7 · 2 2 ( 1 Η，m )， 7 · 6 4 ( 1 Η，m )， 7 . 8 3 ( 1 Η，d )， 8 · 5 8 ( 1 Η，d )， 8 · 7 8 ( 1 Η，s )， 10.60(lH，s)。 L R M S ： m / z 566 (M+1)+。 實施例7 5 — {5 —〔4 — (2 —羥乙基）六氫吡啡—1—基 磺醯基〕2 —正丙氧苯基} 一 3 -丙基一 2 -（吡啶一 2 —基）甲基—2，6 —二氫一 7H —吡唑並〔4，3 — d 〕嘧啶一 7 -酮 由製備例20之標題化合物及1 一（2 -羥乙基）六 經濟部中央標率局員工消費合作社印製 (請先閱讀背面之注意事項再填寫本頁) 氫吡畊依實施例1之步驟製得，呈白色泡沬狀（3 0 % ) 〇 元素分析實測値：C，5 7 · 8 4 ; Η，6 · 4 4 ; N， 15 · 99。C29H37N7〇5S ; 〇 . 1 0 C Η 2 C 1 2 計算値C，57.85;H，6.21;N，16.23 %。 5 ( C D C 1 3 ) :0.95(3H，t)， 本紙張尺度適用中國國家標準（CNS ) A4規格（210X297公釐） _ 37婦 524805 A7 B7 五、發明説明（35) 1 · 1 7 ( 3 Η，t )， 1 · 7 5 ( 2 Η，m )， 2 ·〇 4 ( 2 Η，m )， 2 · 2 8 ( 1 Η，s )， 2 · 5 4 ( 2 Η，t )， 2 · 6 0 ( 4 Η，m )， 2 · 9 8 ( 2 Η，t )， 3 · 1 0 ( 4 Η，m )， 3 · 5 8 ( 2 Η，m )， 4 · 2 5 ( 2 Η，t )， 5 · 6 8 ( 2 Η，s )， 7 · 0 7 ( 1 Η，d )， 7 · 1 7 ( 1 Η，d )， 7 · 2 0 ( 1 Η，. m )， 7 · 6 2 ( 1 Η，m )， 7 . 8 3 ( 1 Η，d )， 8 · 5 8 ( 1 Η，d )， 經濟部中央標準局員工消費合作社印製 (讀先閱讀背面之注意事項再填寫本頁) 8 . 7 8 ( 1 Η，s )， 10.62(lH，s)。 LRMS:m/z 596 (M+1)+。 實施例8 3 —乙基一5 —〔5 —（4 —甲基六氫吡畊一 1—基 磺醯基）2 -正丙氧苯基〕一 2 —（吡啶一 2 —基）甲基 本紙張尺度適用中國國家標準（CNS ) A4規格（210X 297公釐） 〇8 - 一 i Φ 80 24 5 A7 B7 五、發明説明（36) —2，6 -二氫—7H —吡唑並〔4，3 — d〕嘧啶一 7 一酮 由製備例1 8之標題化合物及1 -甲基六氫吡畊依實 施例1之步驟製得，呈白色固體（3 5 % )。 元素分析實測値：C，58.24;H，6.06;N， 17 · 53。C27H33N7〇4S 計算値 C，58.79;H，5.99;N，17.78%。 5(CDCl3):1.12(3H，t)， 1 · 2 6 ( 3 Η，t )， 1 · 9 9 ( 2 Η，m )， 2 · 2 4 ( 3 Η，s )， 2 · 4 5 ( 4 Η，m )， 2 · 9 8 ( 2 Η，q )， 3 · Ο 6 ( 4 Η，· m )， 4 · 2 Ο ( 2 Η，t )， 5 · 6 5 ( 2 Η，s )， 7 · Ο 4 ( 1 Η，d )， 經濟部中央標準局員工消費合作社印製 (讀先閱讀背面之注意事項再填寫本頁) 7 · 1 2 ( 1 Η，d )， 7 · 1 8 ( 1 Η，m )， 7 · 6 Ο ( 1 Η，m )， 7 · 7 8 ( 1 Η，d )， 8 · 5 4 ( 1 Η，d )， 8 · 7 4 ( 1 Η，s )， 10.57(lH，s)。 本紙張尺度適用中國國家標準（CNS ) A4規格（210X297公釐） _ 39 - 524805 A7 B7 五、發明説明（37) L R M S ： m / ζ 552 (M+1)+。 實施例9 3 —乙基一5— {5 —〔4 — (2 —羥乙基）六氫吡 畊一 1 一基磺醯基〕2 -正丙氧苯基} 一 2 —（吡啶一 2 —基）甲基—2，6 —二氫一7H —吡唑並〔4，3 — d 〕嘧D定一 7 -酮 由製備例1 8之標題化合物及1 一（ 2 -羥乙基）六 氫吡畊依實施例1之步驟製得，呈白色固體（3 0 % )。 元素分析實測値：C，5 6 · 1 1 ; Η，6 · 1〇；N， 16 · 15。C28H35N7〇5S ; H2〇計算値 C，56.08;H，6.22;N，16.35%。 (5(CDCl3):1.12(3H，t)， 1 . 3 〇（3 Η ; t )， 2.00(2H，m)， (請先閱讀背面之注意事項再填寫本頁) 經濟部中央標準局員工消費合作社印製 stmQmmtsd JiTlJ±T_iTT-T_iTHXJlTHX XL_i THX T_1 -Li T_i ΤΓ ΤΓ ΤΓ ΤΓ 124242221 /l\ /l\ /(\ /l\ /(V rv Γν /IV 627064044 2 5 5 0 0 5 2 6 0 222333457 \)/ 本紙張尺度適用中國國家標準（CNS ) A4規格（210X297公釐） _4〇 _ 524805 A7 五、發明説明（38) 7 · 1 3 ( 1 Η，d )， 7 · 5 8 ( 1 Η，m )， 7 · 7 8 ( 1 Η，m )， 8 . 5 3 ( 1 Η，d )， 8 · 7 6 ( 1 Η，s )， l〇.58(lH，s)° LRMS:m/z 582 (M+1)+。 實施例1〇 5 —〔2 —乙氧一 5 —（4 —甲基六氫吡畊一1 一基 磺醯基）苯基〕一 3 —正丙基一 2 -（吡啶一 2 -基）甲 基一 2，6 —二氫—7H -吡唑並〔4，3 - d〕嘧啶— 7 —酮 由製備例1 9之標題化合物及1 -甲基六氫吡畊依實 施例1之步驟製得，呈白色泡沬狀（3 2 % )。 元素分析實測値：C，5 7 · 8 2 ; Η，6 · 0 8 ; N， 17. 19%。C27H33N7〇4S ; 經濟部中央標準局員工消費合作社印製 (請先閱讀背面之注意事項再填寫本頁) 0 · 2〇CH2Cl2計算値 C，57 · 45 ; Η，5·92;Ν，17·24%。 5 ( C D C 1 a ):〇.9 5 (3H，t)， 1 · 6 5 ( 3 H，t )， 1 · 7 7 ( 2 H，m )， 2 · 2 8 ( 3 H，s )， 2 · 5 0 ( 4 H，m )， 本纸張尺度適用中國國家標準（CNS ) A4規格（210X297公釐） _斗1 _ 524805 A7 B7 五、發明説明（39) 2 · 9 8 ( 2 Η，t )， 3 · 1 0 ( 4 Η，m )， 4 · 3 8 ( 2 Η，q )， 5 · 6 8 ( 2 Η，s )， 7 ·〇 8 ( 1 Η，d )， 7 . 1 5 ( 1 Η，d )， 7 · 2 3 ( 1 Η，m )， 7.64(lH，m)， 7 · 8 4 ( 1 H，d )， 8 . 5 8 ( 1 H，d )， 8 · 8 〇（1 H，s )， 10.62 (lH，s)。 LRMS:m/z 552 (M+1)+。 實施例1 1 經濟部中央標準局員工消費合作社印製 5 — 〔2 —乙氧一5 — (4 —乙基六氨卩比哄一1—基 磺醯基）苯基〕一 3 -正丙基一 2 —（吡啶一 2 —基）甲 基一 2，6 —二氫一 7H —吡唑並〔4，3 - d〕嘧啶— 7 —酮 由製備例1 9之標題化合物及1 -乙基六氫吡畊依實 施例1之步驟製得，呈白色固體（35%)。 元素分析實測値：C，5 8 · 9 3 ; Η，6 · 2 4 ; N， 17.09°C28H35N7〇4S 計算値 C，59.45;H，6.24;N，17.33%。 -42- (請先閱讀背面之注意事項再填寫本頁) 本紙張尺度適用中國國家標準（CNS ) A4規格（210X 297公釐） 524805 A7 B7 五、發明説明（40) 5 ( C D C 1 3 ):〇.90(3H，t)， 〇.98(3H，t)， 1 · 6 〇（2 Η，m )， 1 · 7 2 ( 2 Η，m )， 2 · 3 6 ( 2 Η，q )， 2 . 5 0 ( 4 Η，m )， 2 · 9 4 ( 2 Η，t )， 3 .〇 6 ( 4 Η，m )， 4 · 3 4 ( 2 Η，d ) ， f 5 · 6 5 ( 2 H，s )， 7 · 0 5 ( 1 H，d )， 7 · 1 0 ( 1 H，d )， 7 · 1 8 ( 1 H，m )， 7.58(lH;m)， 7 · 8 0 ( 1 H，d )， 8 · 5 4 ( 1_H，d )， 8 · 7 6 ( 1 H，s )， 經濟部中央標车局員工消費合作社印製 l〇.58(lH，s)° L R M S ： m / z 566 (M+1)+。 實施例1 2 5 —〔5 — (4 —乙基六氫吡畊—1 一基磺醯基）一 2 -正丙氧苯基〕—3 —正丙基—2 —(吼π定一 2 —基） 甲基一2，6 —二氫一7H —吡唑並〔4，3 — d〕嘧啶 -43- (請先閱讀背面之注意事項再填寫本頁) 本紙張尺度適用中國國家標準（CNS ) A4規格（210X297公釐） 524805 A7 B7 五、發明説明（41) —7 —酮 由製備例2 0之標題化合物及1 -乙基六氫吡哄依實施 例1之步驟製得，呈白色泡沬狀（4 2 % )。 元素分析實測値：C，5 9 · 4 6 ; Η，6 · 4 4 ; Ν， 16 . 5 3 。 C29H37N7〇4S ； 0 · 3 5 Η 2 0 If 算値 C，59 · 44 ; Η，6 · 48 ; N，1 6 · 73% ο (5 ( C D C 1 a ):〇.94(3H，t)， 1 ·〇 3 ( 3 H，t )， 1 · 1 8 ( 3 H，t )， 1 . 7 6 ( 2 H，m )， 2 · 0 4 ( 2 H，m )， 2 · 4 1 ( 2 H，q )， 2 . 5 3 ( 4 H，. m )， 3.〇0(2H，t)， 3 · 1 2 ( 4 H，m )， 4 · 2 5 ( 2 H，t )， 經濟部中央標準局員工消費合作牡印製 5 · 6 7 ( 2 H，s )， 7 · 〇 8 ( 1 Η， 丨d )， 7 · 1 5 ( 1 Η， 丨d )， 7 · 2 3 ( 1 Η ， ，m )， 7 · 6 3 ( 1 Η ，m )， 7 · 8 3 ( 1 Η ，d )， 8 · 5 8 ( 1 Η ’ d )， -44 - (請先閲讀背面之注意事項再填寫本頁) 本纸張尺度適用中國國家標準（CNS ) A4規格（210X297公釐） 524805 A7 B7 五、發明説明（42) 8 · 7 9 ( 1 Η，s )， l〇.60(lH，s)。 L R M S ： m / z 58〇（M+1)+。 實施例1 3 5 —〔5 — (4 —乙基六氫吡畊—1 一基磺醯基）— 2 -正丙氧苯基〕—3 -正丙基一 2 -（吼卩定一 3 —基） 甲基一 2，6 —二氫一 7H —吡唑並〔4，3 — d〕嘧D定 —7 -酮 由製備例2 1之標題化合物及1 -乙基六氫吡畊依實 施例1之步驟製得，呈白色泡沬狀（3 9 % )。 元素分析實測値：C，5 9 . 2 5 ; Η，6 · 4 7 ; N，16.73°C29H37N7〇4S; 0 · 25CH2CI2 計算値 C，59 · 65 ; Η，6·40;Ν，16·79%。 (5 ( C D C 1 3 ) :0.92(3H，t)， 0 · 9 8 ( 3 H，t )， 經濟部中央標準局員工消費合作社印製 (請先閱讀背面之注意事項再填寫本頁) 1 · 1 4 ( 3 H，t )， 1 · 7 4 ( 2 H，m )， 2 ·〇 0 ( 2 H，m )， 2 · 3 7 ( 2 H，q )， 2 · 5 0 ( 4 H，m )， 2 · 8 8 ( 2 H，t )， 3 · 0 5 ( 4 H，m )， 本紙張尺度適用中國國家標準（CNS ) A4規格（21 OX 公釐） Γ45 - 524805 A7 B7 五、發明説明（43) 4 · 2 0 ( 2 Η，t )， 5 . 5 4 ( 2 Η，s )， 7 · 1 〇（1 Η，d )， 7 · 2 2 ( 1 Η，m )， 7 · 5 3 ( 1 Η，d )， 7 · 7 9 ( 1 Η，d )， 8 · 5 4 ( 2 Η，m )， 8 · 7 4 ( 1 Η，s )， 10.58(lH，s)° LRMS:m/z 58〇（M+1)+。 實施例1 4 3 —乙基一5 —〔5 — (4 —乙基六氫吡畊一1 一基 礦釀基）一 2 —正丙氧苯基〕—2 -（塔啡一 3 —基）甲 基—2，6 -二氫—7H —吡唑並〔4，3 — d〕嘧啶— 7 —酮 經濟部中央標準局員工消費合作社印製 (請先閲讀背面之注意事項再填寫本頁) 由製備例2 9之標題化合物及1 -乙基六氫吡畊依實 施例1之步驟製得，呈固體（4 0 % )。 元素分析實測値：C，5 5 · 7 3 ; Η，6 . 0 7 ; N， 18 . 93 。C27H34N8〇4S ; 0 . 75H2〇計算値 C，55.89 ;Η，6·17;Ν，19.31%。 5(CDCl3):1.10(3H，t)， 1 · 1 5 ( 3 Η，t )， 1 · 3 4 ( 3 Η，t )， 本紙張尺度適用中國國家標準（CNS ) Α4規格（210Χ 297公釐） -46 - 524805 A7 B7 五、發明説明（44) 2 . 0 4 ( 2 H ^ m )， 2 . 4 0 ( 2 Η，q )， 2 · 5 〇（4 Η，m )， 3.08(6H，m)， 4 · 2 4 ( 2 H，t )， 5.88(2H，s)， 7 · 1 5 ( 1 H，d )， 7 · 4 6 ( 2 H，m )， 7 · 8 2 ( 1 H，d )， 8.76 (lH，s)， 9 · 1 5 ( 1 H，d )， 1 〇· 6 0 ( 1 H，s )。 LRMS:m/z 567 (M+1)+。 實施例1 5 經濟部中央標準局員工消費合作社印¾ (請先閱讀背面之注意事項再填寫本頁) 5 —〔5 —（4 一乙基六氫吡畊—1 一基磺醯基）2 一正丙氧苯基〕—3 —正丙基一 2 -（嗒畊一 3 —基）甲 基一 2，6 —二氫—7H —吡唑並〔4，3 — d〕嘧啶— 7 -酮 由製備例3 0之標題化合物及1 -乙基六氫吡畊依實 施例1之步驟製得，呈白色固體（3 2 % )。 元素分析實測値：C，5 7 · 6 1 ; Η，6 · 1 1 ; N， 19.1〇°C28H36N8〇4S計算値 C，57.91;H，6.25;N， 19.30%。 本纸張尺度適用中國國家標準（CNS ) A4規格（210X 297公釐） · 4了 524805 A7 B7 五、發明説明（45) (5 ( C D C 1 a ):〇.92(3H，t)， 0 · 9 8 ( 3 Η，t )， 1 · 1 2 ( 3 Η，t )， 1 · 7 5 ( 2 Η，m )， 2 · 0 〇（2 Η，m )， 2.37(2H，d)， 2 · 4 8 ( 4 Η，m )， 3 ·〇〇（2 Η ， t )， 3 · 0 5 ( 4 Η，m )， 4.20(2H，t)， 5 · 8 7 ( 2 H，s )， 7 · 1 2 ( 1 H，d )， 7 · 4 2 ( 1 H，m )， 7 · 4 6 ( 1 H，· d )， 7 · 8 0 ( 1 H，d )， 8 · 7 4 ( 1 H，s )， 9 · 1 2 ( 1 H，d )， 經濟部中央標準局員工消費合作社印製 (讀先閱讀背面之注意事項再填寫本頁) l〇.62(lH，s)° L R M S ： m / z 581(M+1)+。 寳施例1 6 5 —〔5— (4 —乙基六氫吡哄一 1 一基磺醯基）一 2 -正丙氧苯基〕一 3 -正丙基—2 —(塔啡一 4 一基） 甲基一2，6 —二氫—7H -吡唑並〔4，3 — d〕嘧啶 本紙張尺度適用中國國家標準（CNS ) A4規格（210'乂 297公釐） -48 _ 524805 Α7 Β7 五、發明説明（46) —7 —酮 由製備例3 1之標題化合物及1 -乙基六氫吡畊依實 施例1之步驟製得，呈淺褐色固體（2 0 % )。 5 ( C D C 1 3 ) :l.〇l(6H，m)， 1 · 1 8 ( 3 Η，t )， 1 · 8 7 ( 2 Η，m )， 2 · Ο 4 ( 2 Η，m )， 2 · 4 1 ( 2 Η，q )， 2 · 5 5 ( 4 Η，m )， 2 · 9 5 ( 2 Η，t )， 3 · 1 2 ( 4 Η，m )， 4 · 2 6、（ 2 Η，t )， 5 . 8 Ο ( 2 Η，s )， 7 · 1 5 ( 1 Η，. d )， 7 · 4 Ο ( 1 Η，d )， 7 · 8 6 ( 1 Η，d )， 8 · 8 5 ( 1 Η，s )， 經濟部中央標準局員工消費合作社印製 (請先閲讀背面之注意事項再填寫本頁) 9 · 1 4 ( 1 Η，d )， 9 · 2 Ο ( 1 Η，s )， l〇.99(lH，s)° LRMS:m/z 581(Μ+1)+。 實施例1 7 5 —〔5— (4 —乙基六氫吡哄—1—基磺醯基）一 本纸張尺度適用中國國家標準（CNS ) Α4規格（210Χ 297公釐） _ 49 _ 524805 Α7 Β7 五、發明説明（47) 2 -正丙氧苯基〕一 3 -正丙基一 2—(嘧啶一 4 一基） 甲基一 2，6 —二氫一 7H —吡唑並〔4，3 — d〕嘧啶 —7 —酮 由製備例3 2之標題化合物及1 -乙基六氫吡畊依實 施例1之步驟製得，呈泡沬狀（5 8 % )。 元素分析實測値：C，5 7 · 3 1 ; Η，6 · 2 1 ; N， 18 · 98。C28H36N8〇4S 計算値 C，57.91;H，6.25;N，19.30%。 5 ( C D C 1 3 ) :0.92(3H，t)， Ο · 9 7 ( 3 Η，t )， 1 · 1 2 ( 3 Η，t )， 1 · 7 3 ( 2 Η，m )， 2 · Ο Ο ( 2 Η，m )， 2 · 3 8 ( 2 Η，· q )， 2 · 5 9 ( 4 Η，m )， 2 · 9 2 ( 2 Η，t )， 3 . Ο 4 ( 4 Η，m )， 經濟部中央標準局員工消費合作社印^ (請先閱讀背面之注意事項再填寫本頁) 4 · 2 Ο ( 2 Η，t )， 5.60(2H，s)， 6 · 9 6 ( 1 Η，d )， 7 · 1 2 ( 1 Η，d )， 7 · 8 〇（1 Η，d )， 8 · 6 4 ( 1 Η，d )， 8 · 7 5 ( 1 Η，s )， 本紙張尺度適用中國國家標準（CNS ) A4規格（210X297公釐） _ 5〇 A7 524805 __B7 五、發明説明（48) l〇.63(lH，s) 〇 LRMS:m/z 5 81(M+1)+。 (請先閱讀背面之注意事項再填寫本頁) 實施例1 8 5 —〔 5 —（ 4 —乙基六氫吡畊一 1 一基磺醯基）— 2 -正丙氧苯基〕—3 -正丙基一 2 -（嘧啶一 5 -基） 甲基一2，6 —二氫—7H —吡唑並〔4，3 — d〕嘧啶 一 7 -酮 由製備例3 4之標題化合物及1 -乙基六氫吡畊依實 施例1之步驟製得，呈乳泡沬（cream foam )狀（4 4 % )° 元素分析實測値：C，5 7 ·〇0 ; Η，6 · 2 0 ; N， 18 · 42。C28H36N8〇4S ； 0 . 1 5 C Η 2 C 1 2 計算値C，56:98;H，6.17;N，18.88 %。 5 ( C D C 1 3 ) :〇.99(6H，m)， 1 · 1 1 ( 3 Η，t )， - 經濟部中央標準局員工消費合作社印製 1 · 7 8 ( 2 Η，m )， 2 · 0 0 ( 2 Η，m )， 2 · 3 7 ( 2 Η，q )， 2 · 5 〇（4 Η，m )， 2 . 9 4 ( 2 Η ^ m )， 3 . 0 5 ( 4 Η，m )， 4 · 2 1 ( 2 Η ， t )， -51 - 本紙張尺度適用中國國家標準（CNS ) A4規格（210X297公釐） 524805 A7 B7_ 五、發明説明（49) 5 · 5 1 ( 2 Η，s )， 7.1〇（lH，d)， 7 · 8 〇（1 Η，d )， 8 · 6 4 ( 2 Η，s )， 8 · 7 5 ( 1 Η，s )， 9 · 1 5 ( 1 Η，s )， l〇.64(lH，s)。 L R M S ： m / z 581(M+1)+。 實施例1 9 3 —乙基一5 —〔5 — (4 —乙基六氫吡畊一 1 一基 磺醯基）一 2 —正丙氧苯基〕一2 —（吡畊一 2 —基）甲 基—2，6 —二氫—7H —吡唑並〔4，3 — d〕嘧啶一 7 —酮 · 由製備例3 5之標題化合物及1 -乙基六氫吡畊依實 施例1之步驟製得，呈灰色（off-white )泡沬狀（4 7 % )0 經濟部中央標率局員工消費合作社印¾ (請先閱讀背面之注意事項再填寫本頁) 5 ( C D C 1 3 ) :1.01(3H，t)， 1 · 1 5 ( 3 Η，t )， 1 · 3 7 ( 3 Η，t )， 2.02(2H，m)， 2 . 3 9 ( 2 H > q )， 2 · 5 0 ( 4 H，m )， 3 · 0 8 ( 6 H，m )， 本紙張尺度適用中國國家標準（CNS ) A4規格（210X 297公釐） _ 52 _ 524805 A7 B7 五、發明説明（50) 4 · 2 4 ( 2 Η，t )， 5 · 7 〇（2 Η，s )， 7 . 1 5 ( 1 Η，d )， 7 · 8 2 ( 1 Η，d )， 8 · 5 2 ( 3 Η，m )， 8 · 7 8 ( 1 Η，s )， l〇.6〇（lli，s) ° L R M S ： m / z 567 (M+1)+。 實施例2〇 5 —〔 5 — ( 4 —乙基六氧吼哄—1 —基磺醯基） —2 -正丙氧苯基〕一 3 -正丙基—2 —(吼哄—2—基 )甲基一2，6 —二氫一7H —吡唑並〔4，3 — d〕嘧 b定一 7 -醒 由製備例3 6之標題化合物及1 -乙基六氫吡畊依實 施例1之步驟製得，呈白色固體（37%)。 經濟部中央標準局員工消費合作社印製 (請先閱讀背面之注意事項再填寫本頁) 元素分析實測値：C，5 6 · 8〇；Η，6 · 1 1 ; N， 18 · 84 。C28H36N8〇4S ; 0 · 80H2〇計算値 C，56.51 ;H，6.37 ;N，18.83%。 5 ( C D C 1 a ) :0.99 (6H，m)， l.l〇（3H，t)， 1 · 7 8 ( 2 H，m )， 2 · 0 〇（2 H，m )， 2 · 3 8 ( 2 H，Q )， 本紙張尺度適用中國國家標準（CNS ) A4規格（210X297公釐） _ 53 _ 524805 A7 B7 五、發明説明（51) 2 · 4 8 ( 4 Η，m )， 3 · Ο Ο ( 2 Η，t )， 3 ·〇 5 ( 4 Η，m )， 4 · 2 2 ( 2 Η，t )， 5 · 6 8 ( 2 Η，s )， 7. · 1 4 ( 1 Η，d )， 7 · 8 Ο ( 1 Η，d )， 8.47(lH，s)， 8 · 5 Ο ( 2 Η，s )， 8 · 7 4 ( 1 Η，s )， 10.62(lH，s)。 L R Μ S ： m / z 581(M+1)+。 實施例2 1 * 經濟部中央標隼局員工消費合作社印製 5 —〔2 —甲氧一5 —（4 —甲基六M吼啡一1—基 磺醯基）苯基〕一 3 —正丙基—1 一（吡啶—2 —基）甲 基_1，6 —二氫—7H —吡唑並〔4，3 — d〕嘧啶— 7 -酮 由製備例4 1之標題化合物及1 -甲基六氫吡畊依實 施例1之步驟製得，呈白色結晶固體（1 5 % )。 元素分析實測値：C，5 7 · 9 3 ; Η，5 · 7 5 ; N， 18.00°C26H31N7〇4S 計算値 C，58.10; Η，5·77;Ν，18.25%。 5(CDCl3):l.〇0(3H，t)， -54- (請先閱讀背面之注意事項再填寫本頁) 本纸張尺度適用中國國家標準（CMS ) A4規格（210X297公釐） 524805 Α7 Β7 五、發明説明（52) 1 · 8 7 ( 2 Η，m )， 2 · 3 〇（3 Η，s )， 2 · 5 Ο ( 4 Η，m )， 2 · 9 8 ( 2 Η，m )， 3 · 1 2 ( 4 Η，m )， 4 · 1 2 ( 3 Η，s )， 5 · 9 6 ( 2 Η，s )， 7 · Ο 〇（1 Η，d )， 7 · 1 8 ( 2 Η，m )， 7 · 6 Ο ( 1 Η，m )， 7 · 8 8 ( 1 Η，d )， 8 · 5 8 ( 1 Η，d )， 8 . 8 5 ( 1 Η，s )， 10.68(lH，s)。 LRMS:m/z 538 (Μ+1)+。 實施例2 2 經濟部中央標準局員工消費合作社印^ (請先閱讀背面之注意事項再填寫本頁) 5 —〔5 —（4 —乙基六氨吼啡一 1—基擴釀基）— 2 —正丙氧苯基〕—1— (3 —甲氧吡啶一2 —基）甲基 —3 —正丙基一 1，6 —二氫一 7Η —吡唑並〔4，3 -d〕嚼D定一 7 —酮 由製備例4 7之標題化合物及1 -乙基六氫吡畊依實 施例1之步驟製得，呈白色固體（27%)。 元素分析實測値：C，5 8 · 8 3 ; Η，6 · 4 8 ; N， 本纸張尺度適用中國國家標準（CNS ) Α4規格（21〇X297公釐） _ 55 - 524805 A7 B7 五、發明説明（53) 15.76°C3〇H39N7〇5S 計算値 C，59.09;H，6.45;N，16.08%。 (5(CDCl3)：l.〇〇(6H^m)^ 1 · 1 8 ( 3 Η，t )， 1 · 8 7 ( 2 Η，m )， 2 ·〇 2 ( 2 Η，m )， 2 · 4 〇（2 Η，q )， 2 · 5 6 ( 4 Η，m )， 2 · 9 6 ( 2 Η，t )， 3 · 1 3 ( 4 Η，m )， 3 · 8 4 ( 3 Η，s )， 4 . 2 4 ( 2 Η，t )， 5 · 9 8 ( 2 Η，s )， 7 · 1 4 ( 3 Η，. m )， 7 · 8 3 ( 1 Η，d )， 8.02(lH，d) ， 8 · 8 7 ( 1 H，s )， 經濟部中央標準局員工消費合作社印製 (讀先閱讀背面之注意事項再填寫本頁) l〇.80(lH，s)。 L R M S ： m / z 610(M+1)+。 實施例2 3 1 一（6 —胺基吡啶—2 —基）甲基一 5 —〔 5 —（ 4 —乙基六氫吡畊一 1—基磺醯基）一 2 -正丙氧苯基〕 —3 -正丙基—1，6 -二氫一 7H—吡唑並〔4，3 — 本紙張尺度適用中國國家標準（CNS ) A4規格（210X297公釐）' 524805 A7 ___ B7 五、發明説明（54) d〕嘧D定一 7 -酮 由製備例5 0之標題化合物及1 -乙基六氫吡畊依實 施例1之步驟製得，呈白色固體（44%)。 元素分析實測値：C，5 8 · 3 1 ; Η，6 · 4 5 ; N， 18.52°C29H38N8〇4S 計算値 經濟部中央標準局員工消費合作社印製 7ί THX T_i THX ΤΊ- Ji Ji Jl TT- Ji Ji Ji ΤΊ- ΤΊ- ΤΊ- T_1 .____ r 3 ΤΓ ΤΓ ΤΓ- ΤΓ- ΤΓ- T_i T_i ΤΓ- ΤΓ- ΤΓ- ΤΓ- ΤΓ- ΤΓ- p T_i ΤΓ ^ _ LO *~- oo 00 CXI 〇〇 44 CO CV1 OO CO IX t—- 1± 1± rH 1± /V . c /(V /(\ /' /(V rv /^' /(\ /l\ /(\ /(\ /l\ /IV rv rv ^^' /IV 00 8D78526845045554588 5C 1804591247231388·. ， x(\ ···_····_··_···♦ 010 C511222234456677781Ji THX Ji TT- Ji THX THX ΤΓ * Li ΤΓ Li Li LI Li 2 2 3 4 2 4 2 Γν κ (\ / IV xiv / IV / {V 6 4 6 0 8 0 5 7 0 2 5 9 1 2 1 2 2 2 2 3 4 x) y \ ly 1 / mmsmtmt -36- The paper size is applicable to Chinese National Standard (CNS) A4 (21〇X 297 mm) 524805 A7 B7 V. Description of the invention (34) 5 · 6 6 (2 Η, s), 7.0 0 (1 Η, d), 7 · 1 5 (1 Η, d), 7 · 2 2 (1 Η, m), 7 · 6 4 (1 Η, m ), 7.8 3 (1 Η, d), 8 · 5 8 (1 Η, d), 8 · 7 8 (1 Η, s), 10.60 (lH, s). L R M S: m / z 566 (M + 1) +. Example 7 5 — {5 — [4 — (2-hydroxyethyl) hexahydropyridin-1-ylsulfonyl] 2-n-propoxyphenyl} 3 -propyl-2-(pyridine-2 -Methyl) methyl-2,6-dihydro-7H-pyrazolo [4,3 — d] pyrimidin-7-one was prepared from the title compound of Preparation 20 and 1- (2-hydroxyethyl) Hex Printed by the Central Standards Bureau Staff Consumer Cooperative (please read the precautions on the back before filling out this page) Hydropyridine was prepared according to the procedure of Example 1 and showed a white bubble shape (30%). C, 5 7 · 8 4; Η, 6 · 4 4; N, 15 · 99. C29H37N7〇5S; 0.10 C Η 2 C 1 2 Calculate 値 C, 57.85; H, 6.21; N, 16.23%. 5 (CDC 1 3): 0.95 (3H, t), this paper size applies Chinese National Standard (CNS) A4 (210X297 mm) _ 37 women 524805 A7 B7 V. Description of the invention (35) 1 · 1 7 (3 Η, t), 1 · 7 5 (2 Η, m), 2 · 〇 4 (2 Η, m), 2 · 2 8 (1 Η, s), 2 · 5 4 (2 Η, t), 2 · 6 0 (4 Η, m), 2 · 9 8 (2 Η, t), 3 · 1 0 (4 Η, m), 3 · 5 8 (2 Η, m), 4 · 2 5 (2 Η , T), 5 · 6 8 (2 Η, s), 7 · 0 7 (1 Η, d), 7 · 1 7 (1 Η, d), 7 · 2 0 (1 Η,. M), 7 · 6 2 (1 Η, m), 7. 8 3 (1 Η, d), 8 · 5 8 (1 Η, d), printed by the Consumer Cooperatives of the Central Bureau of Standards of the Ministry of Economic Affairs Fill out this page again) 8. 7 8 (1 Η, s), 10.62 (lH, s). LRMS: m / z 596 (M + 1) +. Example 8 3 -Ethyl-5-[5-(4-methylhexahydropyridine-1 -ylsulfonyl) 2-n-propoxyphenyl] -2-(pyridine-2-yl) methyl Paper size applies Chinese National Standard (CNS) A4 specification (210X 297 mm) 〇8-a i Φ 80 24 5 A7 B7 V. Description of the invention (36) —2,6 -dihydro-7H —pyrazolo [4 3, d] Pyrimidine-7 monoketone was prepared from the title compound of Preparation Example 18 and 1-methylhexahydropyridine according to the procedure of Example 1 as a white solid (35%). Elemental analysis: 値: C, 58.24; H, 6.06; N, 17 · 53. C27H33N704. Calculated 値 C, 58.79; H, 5.99; N, 17.78%. 5 (CDCl3): 1.12 (3H, t), 1 · 2 6 (3 Η, t), 1 · 9 9 (2 Η, m), 2 · 2 4 (3 Η, s), 2 · 4 5 ( 4 Η, m), 2 · 9 8 (2 Η, q), 3 · Ο 6 (4 Η, · m), 4 · 2 Ο (2 Η, t), 5 · 6 5 (2 Η, s) , 7 · Ο 4 (1 Η, d), printed by the Consumer Cooperatives of the Central Standards Bureau of the Ministry of Economic Affairs (read the precautions on the back before filling out this page) 7 · 1 2 (1 Η, d), 7 · 1 8 (1 Η, m), 7 · 6 Ο (1 Η, m), 7 · 7 8 (1 Η, d), 8 · 5 4 (1 Η, d), 8 · 7 4 (1 Η, s) , 10.57 (lH, s). The size of this paper applies the Chinese National Standard (CNS) A4 specification (210X297 mm) _ 39-524805 A7 B7 V. Description of the invention (37) L R M S: m / ζ 552 (M + 1) +. Example 9 3 —Ethyl-5 — {5 — [4 — (2-hydroxyethyl) hexahydropyridine-1 1-sulfofluorenyl] 2 -n-propoxyphenyl} 2 — (pyridine-1 2 -Methyl) methyl-2,6-dihydro-7H-pyrazolo [4,3-d] pyrimidin-7-one was prepared from the title compound of Preparation 18 and 1- (2-hydroxyethyl) Hexahydropyridine was prepared according to the procedure of Example 1 as a white solid (30%). Elemental analysis: 値: C, 5 6 · 11; Η, 6 · 10; N, 16 · 15. C28H35N7〇5S; H20 calculated 値 C, 56.08; H, 6.22; N, 16.35%. (5 (CDCl3): 1.12 (3H, t), 1.3 (0) (3 Η; t), 2.00 (2H, m), (Please read the notes on the back before filling this page) Employees of the Central Standards Bureau of the Ministry of Economic Affairs Printed by a consumer cooperative stmQmmtsd JiTlJ ± T_iTT-T_iTHXJlTHX XL_i THX T_1 -Li T_i ΤΓ ΤΓ ΤΓ ΤΓ 124242221 / l \ / l \ / (\ / l \ / (V rv Γν / IV 627064044 2 5 5 0 0 5 2 6 0 222333457 \) / This paper size applies to Chinese National Standard (CNS) A4 specification (210X297 mm) _4〇_ 524805 A7 V. Description of invention (38) 7 · 1 3 (1 Η, d), 7 · 5 8 (1 Η, m), 7 · 7 8 (1 Η, m), 8. 5 3 (1 Η, d), 8 · 7 6 (1 Η, s), 10.58 (lH, s) ° LRMS: m / z 582 (M + 1) +. Example 105— [2-Ethoxy-5— (4-methylhexahydropyridine-1—1-sulfofluorenyl) phenyl] —3-n-propyl 2- (pyridine-2-yl) methyl-2,6-dihydro-7H-pyrazolo [4,3-d] pyrimidin-7-one was prepared from the title compound of Preparation 19 and 1-methyl Hexahydropyridine was prepared in accordance with the procedure of Example 1 and was white-foamed (32%). Elemental analysis: 値: C, 5 7 · 8 2; Η, 6 · 0 8; N, 17. 19%. C27H33N7〇4S; printed by the Consumer Cooperative of the Central Standards Bureau of the Ministry of Economic Affairs (please read the precautions on the back before filling this page) 0 · 2〇CH2Cl2 to calculate 値 C, 57 · 45; H, 5.92; N, 17.24%. 5 (CDC 1 a): 0.9 5 (3H, t), 1 · 6 5 (3 H, t), 1 · 7 7 ( 2 H, m), 2 · 2 8 (3 H, s), 2 · 50 (4 H, m), this paper size applies to China National Standard (CNS) A4 (210X297 mm) _ 斗 1 _ 524805 A7 B7 V. Description of the invention (39) 2 · 9 8 (2 Η, t), 3 · 1 0 (4 Η, m), 4 · 3 8 (2 Η, q), 5 · 6 8 (2 Η , S), 7.08 (1 (, d), 7.15 (1 Η, d), 7.2.3 (1 Η, m), 7.64 (lH, m), 7 · 8 4 (1 H, d), 8.5 (1 H, d), 8.8 (1 H, s), 10.62 (1 H, s). LRMS: m / z 552 (M + 1) +. Example 1 1 Printed by the Consumer Cooperatives of the Central Bureau of Standards of the Ministry of Economic Affairs of the People's Republic of China. 2- (Pyridyl-2-yl) methyl-2,6-dihydro-7H-pyrazolo [4,3-d] pyrimidin-7-one was prepared from the title compound of Preparation 19 and 1-ethyl Hexahydropyridine was prepared according to the procedure of Example 1 as a white solid (35%). Elemental analysis: 値: C, 5 8 · 9 3; Η, 6 · 2 4; N, 17.09 ° C 28H35N704. Calculate 値 C, 59.45; H, 6.24; N, 17.33%. -42- (Please read the precautions on the back before filling this page) This paper size is applicable to Chinese National Standard (CNS) A4 size (210X 297 mm) 524805 A7 B7 V. Description of invention (40) 5 (CDC 1 3) : 0.90 (3H, t), 0.98 (3H, t), 1.6 〇 (2 Η, m), 1 · 7 2 (2 Η, m), 2 · 3 6 (2 Η, q ), 2.5 0 (4 Η, m), 2. 9 4 (2 Η, t), 3.06 (4 Η, m), 4 · 3 4 (2 Η, d), f 5 · 6 5 (2 H, s), 7 · 0 5 (1 H, d), 7 · 1 0 (1 H, d), 7 · 1 8 (1 H, m), 7.58 (lH; m), 7 · 8 0 (1 H, d), 8 · 5 4 (1_H, d), 8 · 7 6 (1 H, s), printed by the Consumer Cooperative of the Central Bureau of Standard Vehicles of the Ministry of Economic Affairs 10.58 (1 H, s) ° LRMS: m / z 566 (M + 1) +. Example 1 2 5 — [5 — (4-ethylhexahydropyridine-1—1-sulfofluorenyl) —2-n-propoxyphenyl] -3—n-propyl-2— —Base) Methyl-2,6 —dihydro-7H —Pyrazolo [4,3 — d] pyrimidine-43- (Please read the precautions on the back before filling this page) The paper size applies to Chinese national standards ( CNS) A4 specification (210X297 mm) 524805 A7 B7 V. Description of the invention (41) -7-one was prepared from the title compound of Preparation Example 20 and 1-ethylhexahydropyridine according to the procedure of Example 1, White vesicles (42%). Elemental analysis: 値: C, 5 9 · 4 6; Η, 6 · 4 4; Ν, 16. 5 3. C29H37N7〇4S; 0 · 3 5 Η 2 0 If 値 C, 59 · 44; Η, 6 · 48; N, 16 · 73% ο (5 (CDC 1 a): 0.94 (3H, t) , 1 · 〇3 (3 H, t), 1 · 1 8 (3 H, t), 1. 7 6 (2 H, m), 2 · 0 4 (2 H, m), 2 · 4 1 ( 2 H, q), 2.5 3 (4 H,. M), 3.00 (2H, t), 3 · 1 2 (4 H, m), 4 · 2 5 (2 H, t), Consumption cooperation of employees of the Central Bureau of Standards of the Ministry of Economic Affairs printed 5 · 6 7 (2 H, s), 7 · 〇8 (1 Η, 丨 d), 7 · 1 5 (1 Η, 丨 d), 7 · 2 3 (1 Η,, m), 7 · 6 3 (1 Η, m), 7 · 8 3 (1 Η, d), 8 · 5 8 (1 Η 'd), -44-(Please read the Please fill in this page for the matters needing attention) The paper size is applicable to Chinese National Standard (CNS) A4 specification (210X297 mm) 524805 A7 B7 V. Description of the invention (42) 8 · 7 9 (1 Η, s), l60.60 (lH, s). LRMS: m / z 58〇 (M + 1) +. Example 1 3 5 — [5 — (4-ethylhexahydropyridine — 1 monosulfonyl) — 2 —n Propoxyphenyl] -3 -n-propyl-2-(stilbidine-3 -yl) methyl-2 6-Dihydro-7H-pyrazolo [4,3-d] pyrimidin-7-one was prepared from the title compound of Preparation 21 and 1-ethylhexahydropyridine according to the procedure of Example 1, It was white foamy (39%). Elemental analysis: 値: C, 59.2. 5; Η, 6. 4 7; N, 16.73 ° C 29H37N7〇4S; 0. 25CH2CI2 Calculate 値 C, 59. 65; Η, 6.40; N, 16.79%. (5 (CDC 1 3): 0.92 (3H, t), 0 · 9 8 (3 H, t), printed by the Consumer Cooperative of the Central Standards Bureau of the Ministry of Economic Affairs ( Please read the notes on the back before filling this page) 1 · 1 4 (3 H, t), 1 · 7 4 (2 H, m), 2 · 〇0 (2 H, m), 2 · 3 7 ( 2 H, q), 2 · 5 0 (4 H, m), 2 · 8 8 (2 H, t), 3 · 0 5 (4 H, m), this paper size applies Chinese National Standard (CNS) A4 Specifications (21 OX mm) Γ45-524805 A7 B7 V. Description of the invention (43) 4 · 2 0 (2 Η, t), 5.5 4 (2 Η, s), 7 · 1 〇 (1 Η, d ), 7 · 2 2 (1 Η, m), 7 · 5 3 (1 Η, d), 7 · 7 9 (1 Η, d), 8 · 5 4 (2 Η, m), 8 · 7 4 (1 Η, s), 10.58 (lH, s) LRMS: m / z 58〇 (M + 1) +. Example 1 4 3 —Ethyl-5 — [5 — (4-Ethylhexahydropyridine-1) 1-N-propoxyphenyl] -2— (Tarphine-3—Base ) Methyl-2,6-dihydro-7H-pyrazolo [4,3-d] pyrimidin-7-one Printed by the Consumer Cooperatives of the Central Standards Bureau of the Ministry of Economic Affairs (Please read the precautions on the back before filling out this page ) It was prepared from the title compound of Preparation Example 29 and 1-ethylhexahydropyridine according to the procedure of Example 1 as a solid (40%). Elemental analysis: 値: C, 5 5 · 7 3; Η, 6. 07; N, 18.93. C27H34N8004S; 0.775H20 calculated 値 C, 55.89; Η, 6.17; N, 19.31%. 5 (CDCl3): 1.10 (3H, t), 1 · 1 5 (3 Η, t), 1 · 3 4 (3 Η, t), this paper size applies to China National Standard (CNS) Α4 specification (210 × 297) (%) -46-524805 A7 B7 V. Description of the invention (44) 2.04 (2H ^ m), 2.40 (2mm, q), 2.5m (4mm, m), 3.08 ( 6H, m), 4 · 2 4 (2 H, t), 5.88 (2H, s), 7 · 1 5 (1 H, d), 7 · 4 6 (2 H, m), 7 · 8 2 ( 1 H, d), 8.76 (lH, s), 9 · 1 5 (1 H, d), 1 · 0.6 (1 H, s). LRMS: m / z 567 (M + 1) +. Example 1 5 Printed by the Consumer Cooperative of the Central Standards Bureau of the Ministry of Economic Affairs (please read the precautions on the back before filling out this page) 5 — [5 — (4 monoethylhexahydropyridine — 1 monosulfosulfenyl) 2 Mono-n-propoxyphenyl] -3 -n-propyl-2-(da-phen-3-yl) methyl-2,6-dihydro-7H-pyrazolo [4,3-d] pyrimidine-7- The ketone was prepared from the title compound of Preparation 30 and 1-ethylhexahydropyridine according to the procedure of Example 1 as a white solid (32%). Elemental analysis: 値: C, 5 7 · 6 1; Η, 6 · 1 1; N, 19.1 ° C 28H36N8004S Calculate 値 C, 57.91; H, 6.25; N, 19.30%. This paper size applies the Chinese National Standard (CNS) A4 specification (210X 297 mm) · 4 524805 A7 B7 V. Description of the invention (45) (5 (CDC 1 a): 0.92 (3H, t), 0 · 9 8 (3 Η, t), 1 · 1 2 (3 Η, t), 1 · 7 5 (2 Η, m), 2 · 0 〇 (2 Η, m), 2.37 (2H, d), 2 · 4 8 (4 Η, m), 3 · 〇〇 (2 Η, t), 3 · 0 5 (4 Η, m), 4.20 (2H, t), 5 · 8 7 (2 H, s) , 7 · 1 2 (1 H, d), 7 · 4 2 (1 H, m), 7 · 4 6 (1 H, · d), 7 · 8 0 (1 H, d), 8 · 7 4 (1 H, s), 9 · 1 2 (1 H, d), printed by the Consumer Cooperatives of the Central Bureau of Standards of the Ministry of Economic Affairs (read the precautions on the back before filling this page) l.62 (lH, s) ° LRMS: m / z 581 (M + 1) +. Po Example 1 6 5 — [5— (4-ethylhexahydropyridine—1 1-sulfosulfanyl) —2—n-propoxyphenyl] A 3 -n-propyl-2-(taffine-4 -yl) methyl -2,6-dihydro-7H-pyrazolo [4,3 — d] pyrimidine This paper size applies Chinese National Standards (CNS) A4 size (210 '乂 297mm) -48 _ 524805 Α7 Β7 V. Description of the invention (46) —7-one was prepared from the title compound of Preparation Example 31 and 1-ethylhexahydropyridine according to the procedure of Example 1. It was a light brown solid (20%). 5 ( CDC 1 3): 1.0 (6H, m), 1 · 1 8 (3 Η, t), 1 · 8 7 (2 Η, m), 2 · Ο 4 (2 Η, m), 2 · 4 1 (2 Η, q), 2 · 5 5 (4 Η, m), 2 · 9 5 (2 Η, t), 3 · 1 2 (4 Η, m), 4 · 2 6, and (2 Η , T), 5. 8 Ο (2 Η, s), 7 · 1 5 (1 Η,. D), 7 · 4 Ο (1 Η, d), 7 · 8 6 (1 Η, d), 8 · 8 5 (1 Η, s), printed by the Consumer Cooperative of the Central Bureau of Standards of the Ministry of Economic Affairs (please read the notes on the back before filling out this page) 9 · 1 4 (1 Η, d), 9 · 2 Ο (1 H, s), 10.99 (lH, s) ° LRMS: m / z 581 (M + 1) +. Example 1 7 5 — [5— (4-Ethylhexahydropyridine—1-sulfosulfanyl) —A paper size applicable to the Chinese National Standard (CNS) A4 specification (210 × 297 mm) _ 49 _ 524805 Α7 Β7 V. Description of the invention (47) 2-n-propoxyphenyl] -3-n-propyl-2- (pyrimidine-4-yl) methyl-2,6-dihydro-7H-pyrazolo [4 3, d] pyrimidin-7-one was prepared from the title compound of Preparation Example 2 and 1-ethylhexahydropyrine according to the procedure of Example 1, and was in the form of a foam (58%). Elemental analysis of plutonium: C, 5 7 · 3 1; Plutonium, 6 · 2 1; N, 18 · 98. C28H36N8004S calculation 値 C, 57.91; H, 6.25; N, 19.30%. 5 (CDC 1 3): 0.92 (3H, t), 〇 · 9 7 (3 Η, t), 1 · 1 2 (3 Η, t), 1 · 7 3 (2 Η, m), 2 · Ο Ο (2 Η, m), 2 · 3 8 (2 Η, · q), 2 · 5 9 (4 Η, m), 2 · 9 2 (2 Η, t), 3. Ο 4 (4 Η, m), printed by the Consumer Cooperatives of the Central Bureau of Standards of the Ministry of Economic Affairs ^ (Please read the notes on the back before filling out this page) 4 · 2 〇 (2 Η, t), 5.60 (2H, s), 6 · 9 6 (1 Η, d), 7 · 1 2 (1 Η, d), 7 · 8 〇 (1 Η, d), 8 · 6 4 (1 Η, d), 8 · 7 5 (1 Η, s), this Paper size applies Chinese National Standard (CNS) A4 specification (210X297 mm) _ 5〇A7 524805 __B7 V. Description of the invention (48) l0.63 (lH, s) 〇LRMS: m / z 5 81 (M + 1 ) +. (Please read the precautions on the back before filling this page) Example 1 8 5 — [5 — (4 -Ethylhexahydropyridine-1 1-sulfosulfanyl) — 2 -n-propoxyphenyl] -3 -N-propyl-2- (pyrimidin-5-yl) methyl-2,6-dihydro-7H-pyrazolo [4,3-d] pyrimidin-7-one from the title compound of Preparation 3 4 and 1-Ethylhexahydropyridine was prepared in accordance with the procedure of Example 1 and showed a cream foam (44%) °. Elemental analysis found 値: C, 5 7 · 0; Η, 6 · 2 0; N, 18 · 42. C28H36N8〇4S; 0.1 5 C Η 2 C 1 2 Calculate 値 C, 56:98; H, 6.17; N, 18.88%. 5 (CDC 1 3): 0.99 (6H, m), 1 · 1 1 (3 Η, t),-printed by the Consumer Cooperative of the Central Standards Bureau of the Ministry of Economic Affairs 1 · 7 8 (2 Η, m), 2 · 0 0 (2 Η, m), 2 · 3 7 (2 Η, q), 2 · 5 〇 (4 Η, m), 2. 9 4 (2 Η ^ m), 3. 0 5 (4 Η , M), 4 · 2 1 (2 Η, t), -51-This paper size applies to China National Standard (CNS) A4 specification (210X297 mm) 524805 A7 B7_ V. Description of the invention (49) 5 · 5 1 ( 2 Η, s), 7.1〇 (lH, d), 7 · 8 〇 (1 Η, d), 8 · 64 (2 Η, s), 8 · 7 5 (1 Η, s), 9 · 1 5 (1 H, s), 10.64 (1 H, s). L R M S: m / z 581 (M + 1) +. Example 1 9 3 -Ethyl-5-[5-(4-ethylhexahydropyridine-1-1-sulfosulfanyl)-2-n-propoxyphenyl]-2-(pyridine-2 -yl ) Methyl-2,6-dihydro-7H-pyrazolo [4,3-d] pyrimidin-7-one · From the title compound of Preparation Example 5 and 1-ethylhexahydropyridine Example 1 Obtained as an off-white bubble (4 7%) 0 Printed by the Staff Consumer Cooperative of the Central Standards Bureau of the Ministry of Economic Affairs ¾ (Please read the precautions on the back before filling out this page) 5 (CDC 1 3 ): 1.01 (3H, t), 1 · 1 5 (3 Η, t), 1 · 3 7 (3 Η, t), 2.02 (2H, m), 2. 3 9 (2 H > q), 2 · 5 0 (4 H, m), 3 · 0 8 (6 H, m), this paper size applies Chinese National Standard (CNS) A4 specification (210X 297 mm) _ 52 _ 524805 A7 B7 V. Description of the invention (50) 4 · 2 4 (2 Η, t), 5 · 7 〇 (2 Η, s), 7. 1 5 (1 Η, d), 7 · 8 2 (1 Η, d), 8 · 5 2 (3 Η, m), 8 · 7 8 (1 Η, s), 10.60 (lli, s) ° LRMS: m / z 567 (M + 1) +. Example 2 05 — [5 — (4-ethylhexaoxo-1 —ylsulfonyl) — 2 —n-propoxyphenyl] 3-n-propyl — 2 — (Methyl) methyl-2,6-dihydro-7H-pyrazolo [4,3-d] pyrimidine b-a-7-X was carried out by the title compound of Preparation Example 3 and 1-ethylhexahydropyridine Prepared as described in Example 1 as a white solid (37%). Printed by the Employees' Cooperative of the Central Standards Bureau of the Ministry of Economic Affairs (please read the precautions on the back before filling this page) Elemental analysis and actual measurement 値: C, 5 6 · 80; Η, 6 · 1 1; N, 18 · 84. C28H36N8〇4S; 0. 80H2O calculated C, 56.51; H, 6.37; N, 18.83%. 5 (CDC 1 a): 0.99 (6H, m), 110 (3H, t), 1 · 7 8 (2 H, m), 2 · 0 〇 (2 H, m), 2 · 3 8 (2 H, Q), this paper size applies Chinese National Standard (CNS) A4 specification (210X297 mm) _ 53 _ 524805 A7 B7 V. Description of the invention (51) 2 · 4 8 (4 Η, m), 3 · Ο Ο (2 Η, t), 3 · 05 (4 Η, m), 4 · 2 2 (2 Η, t), 5 · 6 8 (2 Η, s), 7. · 1 4 (1 Η, d ), 7 · 8 Ο (1 Η, d), 8.47 (lH, s), 8 · 5 Ο (2 Η, s), 8 · 7 4 (1 Η, s), 10.62 (1H, s). L R MS: m / z 581 (M + 1) +. Example 2 1 * Printed by the Consumer Cooperatives of the Central Bureau of Standards of the Ministry of Economic Affairs of the People's Republic of China. Propyl-1 mono (pyridine-2-yl) methyl_1,6-dihydro-7H-pyrazolo [4,3-d] pyrimidin-7-one was prepared from the title compound of Preparation 4 1 and 1- Methylhexahydropyridine was prepared according to the procedure of Example 1 as a white crystalline solid (15%). Elemental analysis: 値: C, 5 7 · 9 3; Η, 5 · 7 5; N, 18.00 ° C 26H31N7〇4S Calculate 値 C, 58.10; Η, 5.77; N, 18.25%. 5 (CDCl3): 1.0.0 (3H, t), -54- (Please read the precautions on the back before filling this page) This paper size is applicable to Chinese National Standard (CMS) A4 specification (210X297 mm) 524805 Α7 Β7 V. Description of the invention (52) 1 · 8 7 (2 Η, m), 2 · 3 〇 (3 Η, s), 2 · 5 〇 (4 Η, m), 2 · 9 8 (2 Η, m), 3 · 1 2 (4 Η, m), 4 · 1 2 (3 Η, s), 5 · 9 6 (2 Η, s), 7 · 〇〇 (1 Η, d), 7 · 1 8 (2 Η, m), 7 · 6 Ο (1 Η, m), 7 · 8 8 (1 Η, d), 8 · 5 8 (1 Η, d), 8. 8 5 (1 Η, s ), 10.68 (lH, s). LRMS: m / z 538 (M + 1) +. Example 2 2 Printed by the Consumer Cooperatives of the Central Bureau of Standards of the Ministry of Economic Affairs ^ (Please read the precautions on the back before filling out this page) 5 — [5 — (4 —Ethylhexamine 1-based expanded base) — 2-n-propoxyphenyl] -1- (3-methoxypyridine-2-yl) methyl-3-n-propyl-1,6-dihydro-7 一 -pyrazolo [4,3-d] Chelated D7-7-ketone was prepared from the title compound of Preparation 47 and 1-ethylhexahydropyrine according to the procedure of Example 1 as a white solid (27%). Elemental analysis: 値: C, 5 8 · 8 3; Η, 6 · 4 8; N, This paper size applies to China National Standard (CNS) Α4 specification (21 × 297 mm) _ 55-524805 A7 B7 V. Description of the invention (53) 15.76 ° C 3OH39N705S calculated 値 C, 59.09; H, 6.45; N, 16.08%. (5 (CDCl3): 1.0 × (6H ^ m) ^ 1 · 1 8 (3Η, t), 1 · 8 7 (2Η, m), 2 · 02 (2Η, m), 2 · 4〇 (2 Η, q), 2 · 5 6 (4 Η, m), 2 · 9 6 (2 Η, t), 3 · 1 3 (4 Η, m), 3 · 8 4 (3 Η , S), 4. 2 4 (2 Η, t), 5 · 9 8 (2 Η, s), 7 · 1 4 (3 Η,. M), 7 · 8 3 (1 Η, d), 8.02 (lH, d), 8 · 8 7 (1 H, s), printed by the Consumer Cooperative of the Central Standards Bureau of the Ministry of Economic Affairs (read the precautions on the back before filling this page) l80.l (lH, s). LRMS: m / z 610 (M + 1) +. Example 2 3 1 Mono (6-aminopyridine-2-yl) methyl-1 5- [5 — (4-ethylhexahydropyridine 1— Sulfosulfenyl)-2 -n-propoxyphenyl] -3 -n-propyl-1,6-dihydro-7H-pyrazolo [4,3 — This paper size applies to China National Standard (CNS) A4 (210X297 mm) '524805 A7 ___ B7 V. Description of the invention (54) d] Pyrimidine D-7-one was prepared from the title compound of Preparation Example 50 and 1-ethylhexahydropyridine according to the procedure of Example 1. Yes, it was a white solid (44%). Analysis and measurement 値: C, 5 8 · 3 1; Η, 6 · 4 5; N, 18.52 ° C29H38N8〇4S Calculation 値 Printed by the Consumers' Cooperative of the Central Standards Bureau of the Ministry of Economy 7 THX T_i THX ΤΊ-Ji Ji Jl TT- Ji Ji Ji ΤΊ- ΤΊ- ΤΊ- T_1 .____ r 3 ΤΓ ΤΓ ΤΓ- ΤΓ- ΤΓ- T_i T_i ΤΓ- ΤΓ- ΤΓ- ΤΓ- ΤΓ- ΤΓ- p T_i ΤΓ ^ _ LO * ~-oo 00 CXI 〇〇44 CO CV1 OO CO IX t—- 1 ± 1 ± rH 1 ± / V. C / (V / (\ / '/ (V rv / ^' / (\ / l \ / (\ / (\ / l \ / IV rv rv ^^ '/ IV 00 8D78526845045554588 5C 1804591247231388 ·., X (\ ··· _ ··· __ · _ ··· ♦ 010 C511222234456677781

H % 4 8 8 IXN 4 4 6Η mΗ 6 κί\ 2ο m m q m mt s sddddd s \1/ (讀先閱讀背面之注意事項再填寫本頁) 本纸張尺度適用中國國家標準（CNS ) A4規格（210X 297公釐） -57- 524805 A7 B7 五、發明説明（55) LRMS :m/z 595 (M+l) 實施例2 4 1 一（1—甲基咪唑一 2 —基）甲基一5 —〔5 經濟部中央標準局員工消費合作社印^ 4 -甲 -3 -d〕嘧 由 施例1 5 ( C 1 . 1 1 . 8 2 . 0 2 . 2 2 . 5 2 . 8 3 . 1 3 . 7 4 . 2 5.9 6 . 8 6 . 9 7 . 1 7 . 8 基六氫吼哄一 1 一基擴醯基）一 2 -正丙氧苯基〕 正丙基—1，6 —二氫—7H —吡唑並〔4，3 — D定一 7 —酮 製備例5 1之標題化合物及1 -甲基六氫吡哄依實 之步驟製得，呈白色泡沬狀（3 6 % )。 D C 1 3 ) :0.98 (3H，t)， 8 ( 3 Η 4 ( 2 Η 4 ( 2 Η 7 ( 3 Η 0 ·( 4 Η 2 ( 2 Η 0 ( 4 Η 6 ( 3 Η 4 ( 2 Η 0 ( 2 Η 4 ( 1 Η 9 ( 1 Η 6 ( 1 Η 4 ( 1 Η t ) t ) m ) s ) m ) t ) m ) s ) t ) s ) s ) s ) d ) d ) 本紙張尺度適用中國國家標準（CNS ) A4規格（210X 297公釐）-58 (讀先閲讀背面之注意事項再填寫本頁} 524805 A7 __B7_ 五、發明説明（56) 8 · 8 4 ( 1 Η，s )， l〇.94(lH，s)。 L R M S ： m / z 569 (M+1) +。 實施例2 5 5— {5 —〔4— (2 —羥乙基）六氫吡畊一 1—基 磺醯基〕一 2 —正丙氧苯基} 一1 一（1 一甲基咪唑一 2 一基）甲基一 3 —正丙基—1，6 —二氫一 7H —吡唑並 〔4，3 — d〕嘧啶—7 —酮 由製備例5 1之標題化合物及1 一（ 2 —羥乙基）六 氫吡畊依實施例1之步驟製得，呈白色固體（5 5 % )。 5(CDCl3):l.〇〇(3H，t)， 1 · 1 8 ( 3 Η，t )， 1 · 6 6 ( 1 Η，· s )， 1 · 8 4 ( 2 Η，m )， 2 · 0 6 ( 2 Η，m )， 2 · 5 5 ( 2 Η，t )， 經濟部中央標準局員工消費合作社印製 (請先閱讀背面之注意事項再填寫本頁) 2 · 6 2 ( 4 Η，m )， 2 · 9 2 ( 2 Η，t )， 3 · 1 2 ( 4 Η，m )， 3 · 5 8 ( 2 Η，m )， 3 · 7 7 ( 3 Η，s )， 4 · 8 8 ( 2 Η，t )， 5 · 9 〇（2 Η，s )， 本纸張尺度適用中國國家標準（CNS ) Α4規格（210Χ297公釐） _ 59 _ 524805 A7 B7 五、發明説明（57) 6 · 8 5 ( 1 Η，s )， 7 ·〇 0 ( 1 Η，s )， 7 · 1 8 ( 1 Η，d )， 7 · 8 5 ( 1 Η，d )， 8 · 8 〇（1 Η，s )。 L R M S ： m / z 599 (M+1)+。 實施例2 6 5 —〔5 —（4 —乙基六氫吡畊一 1—基磺醯基）— 2 —正丙氧苯基〕一1 一（1 一甲基咪唑一2 —基）甲基 —3 —正丙基—1，6 —二氫一 7H —吡唑並〔4，3 — d〕嘧啶一 7 —酮 由製備例5 1之標題化合物及1 -乙基六氫吡畊依實 施例1之步驟製得，呈白色泡沬狀（6 6 % )。 元素分析實測値：C，5 7 · 4 8 ; Η，6 · 6 0 ; N， 18 · 7 0 。C28H38N8〇4S 計算値 C ，57 · 71 ;Η，6·57;Ν，19.23%。 經濟部中央標準局員工消費合作社印製 (請先閱讀背面之注意事項再填寫本頁) 5 ( C D C 1 3 ) :l.〇〇（6H，m)， 1 · 2 0 ( 3 Η，t )， 1 · 8 4 ( 2 Η，m )， 2 ·〇 5 ( 2 Η，m )， 2 · 4 〇（2 Η，Q )， 2 · 5 4 ( 4 Η，m )， 2 · 9 2 ( 2 Η，t )， 本紙張尺度適用中國國家標準（CNS ) A4規格（210X 297公釐） _ 60 - 524805 A7 B7 五、發明説明（58) 3 · 1 0 ( 4 Η，m )， 3 · 7 6 ( 3 Η，s )， 4 · 2 6 ( 2 Η，t )， 5 · 9 0 ( 2 Η，s )， 6 · 8 6 ( 1 Η，s )， 7 ·〇〇（1 Η ， s )， 7 · 1 6 ( 1 Η，d )， 7 . 8 4 ( 1 Η，d )， 8 · 8 4 ( 1 Η，s )， 10.90(lH，s)° LRMS:m/z 583 (M+1)+。 實施例2 7 1— ( 3，5 —二甲基異鸣唑一 4 一基）甲基一 5 — 〔5 — (4 —甲基六氫吡畊一1 一基磺醯基）一 2 —正丙 氧苯基〕—3 —正丙基—1，6 -一氫/一 7H — D比π坐並〔 4，3 — d〕嘧啶—7 —酮 經濟部中央標準局員工消費合作社印製 (請先閱讀背面之注意事項再填寫本頁) 由製備例5 3之標題化合物及1 -甲基六氫吡畊依實 施例1之步驟製得，呈白色固體（8 3 % )。 元素分析實測値：C，5 7 · 0 2 ; Η，6 · 3〇；N， 16 · 28 。C28H37N7〇5S ；〇· 3〇H2〇計算値 C，56.99;H，6.59;N，16.61%。 (5 ( C D C 1 3 ) :1.0〇（3H，t)， 1 · 1 7 ( 3 H，t )， 本紙張尺度適用中國國家標準（CNS ) A4規格（210X297公釐） Γβΐ ： ^ 524805 A7 ____B7 __ 五、發明説明（59) 1 · 8 3 ( 2 Η，m )， 2 ·〇 4 ( 2 Η，m )， 2 · 2 5 ( 3 Η，s )， 2 · 3 2 ( 3 Η，s )， 2 · 5 0 ( 7 Η，m )， 2 ·· 9 0 ( 2 Η，t )， 3 · 0 9 ( 4 Η，m )， 4 · 2 5 ( 2 Η，t )， 5 · 5 2 ( 2 Η，s )， 7 · 1 4 ( 1 Η，d )， 7 · 8 3 ( 1 Η，d )， 8 · 8 4 ( 1 Η，s )， l〇.86(lH，s)。 L R M S ： m / z 584 (M+1)+。 實施例2 8 經濟部中央標车局員工消費合作社印製 5— { 5 —〔4 — (2 —羥乙基）六氫吡哄—1 一基 磺醯基〕一 2 —正丙氧苯基} 一1 一（3，5 —二甲基異 口号口坐—4 —基）甲基—3 —正丙基—1，6 —二氮一7H 一吡唑並〔4，3 — d〕嘧啶一 7 —酮 由製備例5 3之標題化合物及1 一（ 2 —羥乙基）六 氫吡畊依實施例1之步驟製得，呈白色泡沬狀（5 7 % ) 〇 元素分析實測値·· C，5 6 · 3 3 ; Η，6 · 4 2 ; N， -62- (請先閱讀背面之注意事項再填寫本頁) 本紙張尺度適用中國國家標準（CNS ) Α4規格（210X297公釐） 524805 A7 B7 __ 五、發明説明（60) 15.69 °C29H39N7〇6S 計算値 C，56.75;H，6.41;N，15.98%。 5(CDCl3):l.〇l(3H，t)， 1 · 2 0 ( 3 Η，t )， 1 · 8 6 ( 2 Η，m )， 2 · 0 6 ( 2 Η，m )， 2 · 2 8 ( 1 Η，s )， 2.36(3H，s)， 2 · 5 2 ( 3 Η，s )， 2 . 5 6 ( 2 Η，t )， 2 · 6 2 ( 4 Η，m )， 2 · 9 2 ( 2 Η，t )， 3 · 1 0 ( 4 Η，m )， 3 · 5 8 ( 2 Η，. m )， 4 · 2 8 ( 2 Η，t )， 5 · 5 5 ( 2 Η，s )， 7 · 1 8 ( 1 Η，d )， 經濟部中央標準局員工消費合作社印製 (請先閱讀背面之注意事項再填寫本頁) 7 · 8 6 ( 1 Η，d )， 8 · 8 5 ( 1 Η，s )， l〇.88(lH，s)° LRMS:m/z 614(M+1)+。 實施例2 9 5 —〔2 —乙氧一 5 —（4 —甲基六氣口比哄一 1—基 本紙張尺度適用中國國家標隼（CNS ) A4規格（210X 297公釐） _ 63 _ 524805 A7 B7 五、發明説明（61) 磺醯基）苯基〕一 3 —甲基一 1 一（3，5 —二甲基異鸣 唑一4 —基）甲基一1 ，6 —二氫—7H —吡唑並〔4， 3 - d〕喃π定一 7 —酮 由製備例5 4之標題化合物及1 -甲基六氫吡哄依實 施例1之步驟製得，呈白色固體（8 8 % )。 元素分析實測値·· C，5 4 · 3 3 ; Η，5 · 7 2 ; N， 1 7 . 74。 ； 0 . IOCH2CI2 計算値C，54.80;H，5.72;N， 17.82 %。 5 ( C D C 1 3 ) :1.65(3H，t)， 2 · 2 7 ( 3 Η，s )， 2 · 3 2 ( 3 Η，s )， 2.50(1 OH ，m)， 3 · 1 2 ( 4 H ; m )， 4 · 3 8 ( 2 H，Q )， 5.52(2H，s)， 、 7 · 1 6 ( 1 H，d )， 經濟部中央標準局員工消費合作社印製 (請先閱讀背面之注意事項再填寫本頁) 7 · 8 4 ( 1 H，d )， 8 · 8 8 ( 1 H，s )， 10.85(lH，s)。 L R M S ： m / z 542 (M+1)+。 實施例3〇 5 —〔5 —（4 —甲基六氫吡畊一 1 一基磺醯基）一 本纸張尺度適用中國國家標準（CNS ) A4規格（210X 297公釐） -64- 524805 A7 B7 五、發明説明（62) (請先閱讀背面之注意事項再填寫本頁) 2 -正丙氧苯基〕—1 — 1 (2 —甲基噻唑一 4 一基）甲 基一 3 -正丙基一 1，6 —二氫—7H —吡唑並〔4，3 一 d〕嘧啶一 7 -酮 由製備例5 6之標題化合物及1 -甲基六氫吡畊依實 施例1之步驟製得，呈白色泡沬狀（6 1 % )。 元素分析實測値：C，5 5 · 5 1 ; Η，6 · 1 2 ; N， 16.28°C27H35N7〇4S2 計算値 C，55.36;H，6.02;N，16.74%。 5(CDCl3):l.〇〇(3H，t)， 1 · 1 8 ( 3 Η，t )， 1 · 8 6 ( 2 Η，m )， 2 ·〇 4 ( 2 Η，m )， 2 · 2 8 ( 3 Η，s )， 2 · 5 0 ( 4 Η ; m )， 2 · 6 8 ( 3 Η，s )， 2 · 9 7 ( 2 Η，t )， 3 · 1 2 ( 4 Η ，m )， 經濟部中央標率局員工消費合作社印製 4 • 2 6 ( 2 Η， t )， 5 .8 8 ( 2 Η， S )， 6 • 8 8 ( 1 Η， S )， 7 .1 7 ( 1 Η， d )， 7 • 8 4 ( 1 Η， d )， 8 • 8 8 ( 1 Η， s )， 1 0 · 9 〇 ( 1 Η > s ) -65- 本紙張尺度適用中國國家標準（CNS ) A4規格（210X297公釐） 524805 A7 B7 五、發明説明（63) LRMS:m/z 586 (M+1)+。 實施例3 1 5 —〔5 —（4 一甲基六氫吡哄一 1 一基磺醯基）一 2 —正丙氧苯基〕一1— (1—甲基一1 ，2，4 一二口坐 —5 —基）甲基一 3 —正丙基一 1，6 —二氫一7H —吡 唑並〔4，3 - d〕嘧啶一 7 -酮 由製備例5 9之標題化合物及1 -甲基六氫吡畊依實 施例1之步驟製得，呈白色固體（49%)。 元素分析實測値：C，5 4 · 9 6 ; Η，6 · 3 8 ; N， 21 · 1 7。C26H35N9〇4S 計算値 C，54.82;H，6.19;N，22.13%。 5(CDCl3):l.〇l(3H，t)， 1 · 2 〇（3 Η，. t )， 1.86(2H，m)， 2 ·〇 6 ( 2 H，m )， 2 · 3 ◦ ( 3 H，s )， 經濟部中央標準局員工消費合作社印製 (請先閱讀背面之注意事項再填寫本頁) 2 · 5 〇（4 H，m )， 2 · 9 4 ( 2 H，t )， 3 · 1 2 ( 4 H，m )， 4 · 0 1 ( 3 H，s )， 4 · 2 7 ( 2 H，t )， 5 · 9 7 ( 2 H，s )， 7 · 1 6 ( 1 H，d )， 本紙張尺度適用中國國家標準（CNS ) A4規格（210X297公釐） _ 66 - 524805 A7 B7 五、發明説明（64) 7 · 8 4 ( 1 Η，s )， 7 · 8 6 ( 1 Η，d )， (讀先閱讀背面之注意事項再填寫本頁) 8 · 8 5 ( 1 Η，s )， l〇.96(lH，s)。 LRMS:m/z 570 (M+1)+。 實施例3 2 5— { 5 —〔4 一（2 —羥乙基）六氫吡畊一 1 一基 磺醯基〕一 2 -正丙氧苯基} 一1一（1 一甲基—1，2 ，4 一三唑一 5 —基）甲基一 3 —正丙基一 1 ，6 —二氫 —7 Η —吡唑並〔4，3 - d〕嘧啶一 7 -酮 由製備例59之標題化合物及1 一（2 -羥乙基）六 氫吡畊依實施例1之步驟製得，呈白色泡沬狀（6 2 % ) 0 · 元素分析實測値：C，5 2 . 9 6 ; Η，6 · 4 0 ; N， 20 · 14。C27H37N9〇5S ；〇· 7〇H2〇計算値 經濟部中央標準局員工消費合作社印掣 6 3HHHHHH 91322124 • c /l\ rv /l\ r\ /(V 2D056051 5C280356 c 5 112222 Ν 2 3 6 Η % 9 5 ο 2 Η 3 ο 〇 m m \)/ \)/ \)/ \)y s t m 本紙張尺度適用中國國家標準（CNS ) A4規格（210X 297公釐） · 67 - 524805 A7 B7 五、發明説明（65) 2 · 9 4 ( 2 Η，t )， 3 · 1 2 ( 4 Η，m )， 3 · 5 8 ( 2 Η，m )， 4 ·〇 Ο ( 3 Η，s )， 4 · 3 Ο ( 2 Η，t )， 5 · 9 7 ( 2 Η，s )， 7 · 1 8 ( 1 Η，d )， 7 · 8 2 ( 1 Η，s )， 7 · 8 5 ( 1 Η，d )， 8 · 8 5 ( 1 Η，s )， l〇.98(lH，s)° L R Μ S ： m / z 60〇（M+1)+。 實施例3 3 ‘ 經濟部中央標準局員工消費合作社印製 (讀先閱讀背面之注意事項再填寫本頁) 5 —〔5— (4 —乙基六氣哦哄—1—基礦酸基）一 2 —正丙氧苯基〕一 1 一（1—甲基一 1，2，4 一二口坐 一 5 —基）甲基一3 —正丙基一 1，6 — — Μ— 7H — 口比 唑並〔4，3-d〕嘧啶一7—酮 _由製備例5 9之標題化合物及1 -乙基六氫吡畊依實 施例1之步驟製得，呈白色固體（4 0 % )。 元素分析實測値：C，5 5 · 3 1 ; Η，6 · 6〇；N， 21.〇9°C27H37N9〇4S計算値 C，55.56; Η，6.39 ;N，21.60%。 5 ( C D C 1 3 ) :l.〇2(6H，m)， 本紙張尺度適用中國國家標隼（CNS ) A4規格（210X 297公釐） -68- 524805 A7 B7 五、發明説明（66) 1 · 1 8 ( 3 Η，t )， 1 · 8 6 ( 2 Η，m )， 2 ·〇 6 ( 2 Η，m )， 2 · 4 1 ( 2 Η，q )， 2 · 5 5 ( 4 Η，m )， 2 · 9 4 ( 2 Η，t )， 3.1〇（4H，m)， 4 ·〇〇（3 H ， s )， 4 · 2 6 ( 2 H，t )， 5 · 9 7 ( 2 H，s )， 7.16(lH，d)， 7 · 8 3 ( 1 H，s )， 7 · 8 5 ( 1 H，d )， 8 · 8 4 ( 1 H，. s )， 10.96(lH，s)。 L R M S ： m / z 584(M+1)+。 經濟部中央標率局員工消費合作社印製 (請先閱讀背面之注意事項再填寫本頁) 實施例3 4 5— {5 —〔4一（2 —甲氧乙基）六氫吼啡一1一 基磺醯基〕一 2 —正丙氧苯基} 一1一（1 一甲基一 1， 2，4 一三唑一 5 —基）甲基—3 —正丙基一 1，6二氫 —7 Η —吼嗤並〔4，3 — d〕嘻Β定一 7 —丽 由製備例5 9之標題化合物及1 一（2 —甲氧乙基） 六氫吡畊依實施例1之步驟製得，呈白色固體（4 3 % ) 本紙張尺度適用中國國家標準（CNS ) A4規格（210X297公釐） -69 - 524805 kl B7 五、發明説明（67) 〇 c?(CDCl3):l.〇〇(3H，t)， 1 · 2 0 ( 3 Η，t )， 1 · 8 6 ( 2 Η，m )， 2 · Ο 6 ( 2 Η，m )， 2 · 5 7 ( 6 Η，m )， 2 · 9 2 ( 2 Η，t )， 3 · 1 2 ( 4 Η，m )， 3 · 3 Ο ( 3 Η，s )， 3 · 4 4 ( 2 Η，t )， 4 ·〇〇（3 Η ， s )， 4 · 2 8 ( 2 Η，t )， 5 . 9 8 ( 2 Η，s )， 7 · 1 6 ( 1 Η，. d )， 7 . 8 3 ( 1 Η，s )， 7.85(lH，d)， 8 · 8 6 ( 1 Η，s )， 經濟部中央標隼局員工消費合作社印製 1 〇· 9 5 ( 1 Η，s )。 LRMS:m/z 614(Μ+1)+。 實施例3 5 1 一〔 1— (2 —甲氧乙基）一1 ，2，4 —三卩坐一 5 —基〕甲基一5 —〔5 — (4 —甲基六氫吡哄一 1 一基 磺醯基）—2 —正丙氧苯基〕一 3 -正丙基一 1，6 —二 -70- (請先閱讀背面之注意事項再填寫本頁) 本紙張尺度適用中國國家標準（CNS ) A4規格（210X297公釐） 524805 A7 B7 五、發明説明（68) 氫—7H —吡唑並〔4，3 — d〕喃啶—7 —酮 (讀先閱讀背面之注意事項再填寫本頁) 由製備例6 4之標題化合物及1 -甲基六氫吡畊依實 施例1之步驟製得，呈白色泡沬狀（7 7 % )。 5 ( C D C 1 3 ) ： 0 . 9 7 ( 3 H ^ t )， 1 · 1 6 ( 3 Η，t )， 1 · 8 2 ( 2 Η，m )， 2 ·〇 0 ( 2 Η，m )， 2 · 2 4 ( 3 Η，s )， 2 · 4 6 ( 4 Η，m )， 2.86(2H，t)， . 3 · 2 5 ( 3 Η，s )， 3 · 6 6 ( 2 Η，t )， 4 · 2 2 ( 2 Η，t )， 4 · 5 2 ( 2 Η，. t )， 5 · 9 7 ( 2 Η，s )， 7 · 1 2 ( 1 Η，d )， 7 · 8 〇（2 Η，m )， 經濟部中央標準局員工消費合作社印^ 8 · 8 2 ( 1 Η，s )， l〇.86(lH，s)。 LRMS:m/z 614(M+1)+。 實施例3 6 5 —〔5 —（4 —乙基六氮1:1比畊一 1 一基擴釀基）一 2 —正丙氧苯基〕一 1—〔 1一（2 —甲氧乙基）一1 ， 本纸張尺度適用中國國家標準（CNS ) A4規格（210X 297公釐） -71 - 524805 A7 B7 五、發明説明（69) 2，4 —三唑—5 —基〕甲基一 3 —正丙基一 1 ，6 —二 氫—7H —吡唑並〔4，3 — d〕嘧啶一 7 —酮 由製備例6 4之標題化合物及1 -乙基六氫吡哄依實 施例1之步驟製得，呈白色泡沬狀（6 6 % )。 元素分析實測値：C，5 5 . 1 0 ; Η，6 · 6 2 ; N， ig.YliCzgHnNgOsS 計算値 C，55.49;H，6.58;N，2〇.08%。 5 ( C D C 1 3 ):〇.98(6H，m)， 1 · 1 5 ( 3 H，t )， 1 · 8 〇（2 H，m )， 2 · 0 0 ( 2 H，m )， 2 · 3 7 ( 2 H，q )， 2 · 5 0 ( 4 H，m )， 2 · 9 0 ( 2 H，· t )， 3 · 0 8 ( 4 H，m )， 3 · 2 6 ( 3 H，s )， 3 . 6 8 ( 2 H，t )， 4 · 2 2 ( 2 H，t )， 經濟部中央標準局員工消費合作社印製 (請先閱讀背面之注意事項再填寫本頁) 4 · 6 2 ( 2 H，t )， 5 · 9 6 ( 2 H，s )， 7 · 1 2 ( 1 H，d )， 7 · 8 〇（2 H，m )， 8 · 8 2 ( 1 H，s )， l〇.86(lH，s)° 本紙張尺度適用中國國家標準（CNS ) A4規格（210X 297公釐） -72 - 524805 A7 B7 五、發明説明（70) LRMS:m/z 628 (M+1)+。 實施例3 7 5 —〔5—（4 —乙基六氫吡畊—1—基磺醯基）一 2 -正丙氧苯基〕一1 一（4 —甲基一 1，2，4 一三唑 —3 —基）甲基一3 —正丙基一1，6 —二氧一 7H — D比 唑並〔4，3 - d〕嘧啶一 7 —酮 由製備例6 6之標題化合物及1 -乙基六氫吡畊依實 施例1之步驟製得，呈白色固體（43%)。 元素分析實測値·· C，5 4 · 4 6 ; Η，6 · 3 1 ; N， 21 ·〇8 。C27H37N9〇4S; 〇 · 60Η2〇計算値 C，54.54;H，6.47;N，21.2〇％。 5 ( C D C 1 3 ) :l.〇〇（6H，m)， 1 · 2 0 ( 3 H，. t )， 1 · 8 4 ( 2 H，m )， 2 · 0 6 ( 2 H，m )， 2 · 4 〇（2 H，d )， 經濟部中央標率局員工消費合作社印製 (讀先閱讀背面之注意事項再填寫本頁) 2.56(4H，m)， 2 · 9 2 ( 2 H，t )， 3 . 1 2 ( 4 H，m )， 3 · 7 6 ( 3 H，s )， 4 . 2 8 ( 2 H，t )， 6 · 0 4 ( 2 H，s )， 7 · 1 7 ( 1 H，d )， 本紙張尺度適用中國國家標準（CNS ) A4規格（21〇X 297公釐） -73 _ 524805 A7 B7 五、發明説明（71) 7 · 8 6 ( 1 Η，d )， 8 · 1 0 ( 1 Η，s )， 8 · 8 6 ( 1 Η，s )， l〇.96(lH，s)° LRMS:m/z 584 (M+1)+。 實施例3 8 5 —〔5 —（4 一甲基六氣吼哄一 1—基礦酸基）一 2 —正丙氧苯基〕一1 一（4 一甲基—1，2，4 一三唑 —5 —基）甲基一 3 —正丙基一1 ’ 6 — —氯一7H — 口比 唑並〔4，3 — d〕嘧啶—7 -酮 由製備例6 6之標題化合物及1 -甲基六氫吡畊依實 施例1之步驟製得，呈白色固體（5 1 % )。 元素分析實測値：C，5 3 · 0 7 ; Η，6 · 1 4 ; N， 20 · 48 。 C26H35N9〇4S ; 0 · 8 0 Η 2 Ο ； 〇· 10CH2C12; 0 · 05CH3〇H 計算値 C，52.86;H，6.30;N，21.20%。 經濟部中央標率局員工消費合作社印製 (請先閱讀背面之注意事項再填寫本頁) 5 ( C D C 1 3 ) :l.〇〇（3H，t)， 1 · 2 〇（3 H，t )， 1 · 8 2 ( 2 H，t )， 2 · 0 6 ( 2 H，m )， 2 · 2 8 ( 3 H，s )， 2 · 5 0 ( 4 H，m )， 2 · 9 2 ( 2 H，t )， 本紙張尺度適用中國國家標準（CNS ) A4規格（210X297公釐） _ 74 - 524805 A7 B7 五、發明説明（72) 3 · 1 0 ( 4 Η，m )， 3 · 7 5 ( 3 Η，s )， 4 · 2 7 ( 2 Η，t )， 6 ·〇 4 ( 2 Η，s )， 7 · 1 6 ( 1 Η，d )， 7 · 8 4 ( 1 Η，s )， 7.86(lH，d)， 8 · 8 4 ( 1 H，s )， 1 0 · 9 6 ( 1 H，s )。 LRMS:m/z 57〇（M+1)+。 實施例3 9 5 — {5 —〔4 — (2 —羥乙基）六氫吡畊一 1 一基 磺醯基〕一 2 —正丙氧苯基} 一1 一（4 一甲基一 1，2 ，4 —三唑一 5 —基）甲基—3 —正丙基一 1，6 —二氫 一 7H —吡哩並〔4，3 — d〕嚼D定—7 —酮 經濟部中央標準局員Η消費合作社印¾ 由製備例66之標題化合物及1一（2—羥乙基）六 氫吡哄依實施例1之步驟製得，呈白色固體（3 7 % ) 〇 元素分析實測値：C，5 3 · 4 9 ; Η，6 · 0 4 ; N， 21 . 5〇。C27H37N9〇5S ；〇· 10H2〇計算値 C，53.91;H，6.23;N，20.96%。 5 ( C D C 1 3 ) :l.〇〇（3Ii，t)， 1 · 2 0 ( 3 H，t )， 1 · 8 4 ( 2 H ，m )， -75- (讀先閱讀背面之注意事項再填寫本頁) 本紙張尺度適用中國國家標準（CNS ) Α4規格（210X 297公釐） 524805 A7 B7 經濟部中央標準局員工消費合作社印製 五、發明説明（73) 2 .〇 6 ( 2 Η，m )， 2 · 2 8 ( 1 Η，s )， 2 · 5 6 ( 2 Η，t )， 2 · 6 4 ( 4 Η，m )， 2 · 9 2 ( 2 Η，t )， 3 . 1 4 ( 4 Η，m )， 3 · 5 8 ( 2 Η，m )， 3 · 7 7 ( 3 Η，s )， 4 · 2 8 ( 2 Η，t )， 6 ·〇 2 ( 2 Η，s )， 7 · 1 8 ( 1 Η，d )， 7 · 8 6 ( 1 Η，d )， 8 · 1 〇（1 Η，s )， 8 · 8 6 ( 1 Η，s )， 1 Ο · 9 8 ( 1 Η，s )。 LRMS:m/z 6 0‘0(M+1)+。 實施例4 Ο 5 —〔5— (4 —甲基六氫吡哄一 1—基磺醯基）一 2 —正丙氧苯基〕—1— (1，2，4-鸣二唑—3 —基 )甲基一 3 —正丙基一 1，6 —二氫一7Η —吡唑並〔4 ，3 — d〕喃n定一 7 -酮 由製備例6 7之標題化合物及1 -甲基六氫吡畊依實 施例1之步驟製得，呈固體（3 3 % )。 (請先閲讀背面之注意事項再填寫本頁) 本纸張尺度適用中國國家標準（CNS ) A4規枱（21〇'乂297公釐）-76 - 524805 A7 B7 五、發明説明（74 ) 5(CDCl3):l.〇〇(3H，t)， 1 · 1 8 ( 3 Η，t )， 1 · 8 7 ( 2 Η，m )， 2 · Ο 4 ( 2 Η，m )， 2 · 2 8 ( 3 Η，s )， 2 · 5 Ο ( 4 Η，m )， 2 · 9 4 ( 2 Η，t )， 3 · 1 2 ( 4 Η，m )， 4 . 2 6 ( 2 Η，t )， 6 · Ο 2 ( 2 Η，s )， 7 · 1 7 ( 1 Η，d )， 7 · 8 5 ( 1 Η，d )， 8 · 6 7 ( 1 Η，s )， 8 · 8 8 ( 1 Η，s )， l〇.96(lH，s)° LRMS:m/z 557 (Μ+1)+。 實施例4 1 經濟部中央標準局員工消費合作社印製 (讀先閱讀背面之注意事項再填寫本頁) 1 一；基一5 —〔2 —乙氧一5 —（4 一甲基六氫吼 畊一 1 一基礦酿基）苯基〕一 3 —正丙基一 1，6 -二氫 一 7Η -吡唑並〔4，3 - d〕嘧啶—7 —酮 將製備例86之標題化合物（5 · Og，8 . 8 mmo 1)加入含有第三丁氧化鉀（1 · 2g，1〇 mmo 1 )及第三丁醇（75ml )之攪拌溶液裡，再令 本纸張尺度適用中國國家標準（CNS ) A4規枱（210X297公釐）-77 - 524805 A7 B7 五、發明説明（75) 此混合物迴流加熱2 0小時，經冷卻後減壓蒸發。把得到 的殘餘物在乙酸乙酯（300ml)和水（300ml) 之間分配，然後將分離出來的水相部份以乙酸乙酯萃取（ 3 X 1 5 0 m 1 )。有機溶液經合倂後依續用水（1 5 0 m 1 )和鹽水（1 5 0 m 1 )洗過，乾燥（M g S〇4 )後 減壓蒸發而得到白色固體，此白色固體經乙醚碾製（ trituration )，再於真空下乾燥而得到呈白色細晶體之標題 化合物（4 · 2 9 g )。 元素分析實測値：C，6 0 · 8 4 ; Η，6 · 2 0 ; N， 15 · 08。C28H34N6〇4S 計算値 C，61.08; Η，6·22;Ν，15.26%。 5 ( C D C 1 3 ) : 1 · 〇 1 ( 3 Η，t )， 1.64(3H，t)， 1 · 8 8 ( 2 H，m )， 2 · 2 6 ( 3 H，s )， 2 · 4 8 ( 4 H，m )， 2 · 9 6 ( 2 H，t )， 3 · 1 2 ( 4 H，m )， 經濟部中央標準局員工消費合作社印製 (讀先閲讀背面之注意事項再填寫本頁) 4 · 3 8 ( 2 H，q )， 5 · 7 8 ( 2 H，s )， 7.14(lH，d)， 7 · 2 6 ( 3 H，m )， 7 · 4 0 ( 2 H，m )， 7 · 8 2 ( 1 H，d )， 本紙張尺度適用中國國家標隼（CNS ) A4規栳（210X 297公釐）.78 - 524805 A7 B7 經濟部中央標準局員工消費合作社印製 五、發明説明（76) 8 · 8 4 ( 1 Η，s )， 10.8 0 (lH，s)。 LRMS :m/z 551 (M+l)+。 實施例4 2 1 一节基一5 —〔5 —（4 一甲基六氫/吼哄一 1—基 擴醯基）—2 -正丙氧苯基〕—3 —正丙基一 1 ’ 6 -二 氫一 7 Η —吡並〔4，3 - d〕嘧啶—7 —酮 把氫化鈉（置礦油中’ 1 6 0 m g，4 m m ο 1 )的 6〇％ w/w懸浮液分批加入以冰冷卻且攪拌中的1 一丙 醇（2 0 m 1 )裡，在停止起泡（effervescence )時，添 加實施例4 1之標題化合物（5 5 Omg，lmmo 1 ) 。把形成的混合物迴流加熱9 6小時，令其冷卻並減壓蒸 發。將殘餘物在乙酸乙酯（50ml)及水（50ml) 之間分配，接著把分出來的水相部份用乙酸乙酯（總量 1 〇 0 m 1 )萃取。有機相經合倂後加以乾燥（N a S〇4 )，減壓蒸發，然後將殘餘物以管柱層析法在矽膠上進行 純化，使用的沖提液爲乙酸乙酯：甲醇：〇 · 8 8 0氨水 (95:5:0.5)，結果得到無色泡沬狀的標題化合 物（2 3 〇 m g )。 元素分析實測値：C，6 1 · 6 5 ; Η，6 · 4 8 ; N， 14 · 53。C29H36N6〇4S 計算値 C，61 ·68; Η，6.48; N，14.88%。 5 ( C D C 1 3 ) :0.98(3H，t)， 本紙張尺度適用中國國家標準（CNS ) A4規枱（210X 297公蝥）-79 - (請先閱讀背面之注意事項再填寫本頁 4 524805 A7 B7 五、發明説明（77 ) 1 · 1 5 ( 3 Η，t )， 1.83(2H，m)， 2 · Ο 1 ( 2 Η，m )， 2 · 2 4 ( 3 Η，s )， 2 · 4 6 ( 4 Η，m )， 2 · 9 2 ( 2 Η，t )， 3 ·〇 8 ( 4 Η，m )， 4 · 2 2 ( 2 Η，t )， 5 . 7 3 ( 2 Η，s )， 7 · 1 2 ( 1 Η，d )， 7 · 2 7 ( 3 Η，m )， 7 · 3 6 ( 2 Η，m )， 7 · 8 Ο ( 1 Η，d ); 8 · 8 2 ( 1 Η，s )， 1 1 · 8 4 ( 1 Η，s )。 LRMS:m/z 565 (Μ+1)+。 經濟部中央標準局員工消費合作社印製 (請先閱讀背面之注意事項再填寫本頁) 實施例4 3 1 一（4 —氯苄基）—5 —〔5 —（4 一甲基六氫吼 畊—1 一基磺醯基）一 2 -正丙氧苯基〕一 3 -正丙基一 1，6 —二氫—7Η —吡唑並〔4，3 — d〕嘧啶一 7 — 酮 由製備例8 7之標題化合物及1 -甲基六氫吡畊依實 施例1之步驟製得，呈白色固體（75%)。 本紙張尺度適用中國國家標準（CNS ) A4規枱（210X 297公釐）-80- 經濟部中央標準局員工消費合作社印製 524805 A 7 B7 五、發明説明（78) 兀素分析實測値：C，5 7 · 9 9 ; Η，5 . 9 4 ; N， 13 · 76。C29H35C1N6〇4S 計算値 C，58.14;H，5.89;N，14.〇3%。 5(CDCl3):l.〇〇(3H，t)， 1 · 1 9 ( 3 Η，t )， 1 · 8 6 ( 2 Η，m )， 2 · Ο 6 ( 2 Η，m )， 2 · 2 8 ( 3 Η，s )， 2 · 4 8 ( 4 Η，m )， 2 · 9 4 ( 2 Η，t )， 3 . Ο 8 ( 4 Η，m )， 4 · 2 4 ( 2 Η，t )， 5 · 7 2 ( 2 Η，s )， 7 · 1 5 ( 1 Η，d )， 7 · 2 6 ( 2 Η，d )， 7 · 3 4 ( 2 Η，d )， 7 · 8 2 ( 1 Η，d )， 8 · 8 4 ( 1 Η，s )， 1 Ο . 9 Ο ( 1 Η ^ s ) ° L R Μ S ： m / ζ 599 (Μ+1)+。 實施例4 4 1— (4 —氯干基）—5 —〔2 —乙氧一5 — (4 — 甲基六氣哦啡一 1 一基擴酸基）一苯基〕—3 -正丙基一 本纸張尺度適用中國國家標準（CNS ) A4規桔（210X 297公釐）-81 - (請先閱讀背面之注意事項再填寫本頁) 、\呑 524805 A7 B7 五、發明説明（79 經濟部中央標準局員工消費合作社印製 (請先閱讀背面之注意事項再填寫本頁)H% 4 8 8 IXN 4 4 6Η mΗ 6 κί \ 2ο mmqm mt s sddddd s \ 1 / (Read the precautions on the back before filling out this page) This paper size applies to the Chinese National Standard (CNS) A4 specification (210X 297 mm) -57- 524805 A7 B7 V. Description of the invention (55) LRMS: m / z 595 (M + 1) Example 2 4 1- (1-methylimidazol-2-yl) methyl-5— [5 Seal of the Consumer Cooperatives of the Central Bureau of Standards of the Ministry of Economic Affairs of the People's Republic of China 4 -A-3 -d] Pyrimidine Example 15 (C 1.1.1.2.8 2. 0 2. 2 2. 5 2. 8 3. 1 3 7 4. 2 5.9 6. 8 6. 9 7. 1 7. 8 Hexahydroxanthine-1 1-fluorenyl)-2-n-propoxyphenyl] n-propyl-1,6-dihydro —7H —Pyrazolo [4,3 —D-a-7-one Preparation Example 51 The title compound of 1 and 1-methylhexahydropyridine were prepared according to the procedure, and it appeared as a white foam (36%) . DC 1 3): 0.98 (3H, t), 8 (3 Η 4 (2 Η 4 (2 Η 7 (3 Η 0 · (4 Η 2 (2 Η 0 (4 Η 6 (3 Η 4 (2 Η 0 (2 Η 4 (1 Η 9 (1 Η 6 (1 Η 4 (1 Η t) t) m s s) m) t) m) s) t) s s s s) d) d) Applicable Chinese National Standard (CNS) A4 specification (210X 297mm) -58 (Read the precautions on the back before filling in this page} 524805 A7 __B7_ V. Description of the invention (56) 8 · 8 4 (1 Η, s) , 10.94 (lH, s). LRMS: m / z 569 (M + 1) +. Example 2 5 5— {5 — [4— (2-hydroxyethyl) hexahydropyridine 1— Sulfofluorenyl]-2 -n-propoxyphenyl}-1-(1 -methylimidazole-2 -yl) methyl-3 -n-propyl-1, 6-dihydro-7H-pyrazolo [ 4,3-d] pyrimidin-7-one was prepared from the title compound of Preparation 51 and 1- (2-hydroxyethyl) hexahydropyridine according to the procedure of Example 1 as a white solid (55%) 5 (CDCl3): 1.0 (3H, t), 1 · 18 (3 Η, t), 1 · 6 6 (1 Η, · s), 1 · 8 4 (2 Η, m), 2 · 0 6 (2 Η, m), 2 · 5 5 (2 Η, t ), Printed by the Consumer Cooperatives of the Central Bureau of Standards of the Ministry of Economic Affairs (please read the notes on the back before filling out this page) 2 · 6 2 (4 Η, m), 2 · 9 2 (2 Η, t), 3 · 1 2 (4 Η, m), 3 · 5 8 (2 Η, m), 3 · 7 7 (3 Η, s), 4 · 8 8 (2 Η, t), 5 · 9 〇 (2 Η, s ), This paper size applies the Chinese National Standard (CNS) A4 specification (210 × 297 mm) _ 59 _ 524805 A7 B7 V. Description of the invention (57) 6 · 8 5 (1 Η, s), 7 · 〇 0 (1 Η, s), 7 · 1 8 (1 Η, d), 7 · 8 5 (1 Η, d), 8 · 8 〇 (1 Η, s). LRMS: m / z 599 (M + 1) + Example 2 6 5 — [5 — (4-ethylhexahydropyridine—1-sulfofluorenyl) — 2—n-propoxyphenyl] —1— (1—methylimidazole—2-yl) Methyl-3-n-propyl-1,6-dihydro-7H-pyrazolo [4,3-d] pyrimidin-7-one was prepared from the title compound of Preparation 51 and 1-ethylhexahydropyridine It was obtained according to the procedure of Example 1 and was white foamy (66%). Elemental analysis: 値: C, 5 7 · 4 8; Η, 6 · 6 0; N, 18 · 7 0. C28H38N8〇4S calculated 値 C, 57 · 71; Η, 6.57; N, 19.23%. Printed by the Consumer Cooperatives of the Central Bureau of Standards of the Ministry of Economic Affairs (please read the precautions on the back before filling this page) 5 (CDC 1 3): 1.0 (6H, m), 1 · 2 0 (3 Η, t) , 1 · 8 4 (2 Η, m), 2 · 〇 5 (2 m, m), 2 · 4 〇 (2 Η, Q), 2 · 5 4 (4 Η, m), 2 · 9 2 ( 2 Η, t), this paper size applies Chinese National Standard (CNS) A4 specification (210X 297 mm) _ 60-524805 A7 B7 V. Description of the invention (58) 3 · 1 0 (4 Η, m), 3 · 7 6 (3 Η, s), 4 · 2 6 (2 Η, t), 5 · 9 0 (2 Η, s), 6 · 8 6 (1 Η, s), 7 · 〇 (1 Η, s), 7 · 16 (1 Η, d), 7.8 4 (1 Η, d), 8 · 8 4 (1 Η, s), 10.90 (lH, s) ° LRMS: m / z 583 ( M + 1) +. Example 2 7 1— (3,5-Dimethylisoimidazole—4-yl) methyl—5— [5 — (4-methylhexahydropyridine—1—sulfosulfanyl) —2— N-propoxyphenyl] -3-n-propyl-1,6-monohydro / -7H-D ratio π sitting and [4,3-d] pyrimidine-7-one printed by the Consumer Cooperative of the Central Standards Bureau of the Ministry of Economic Affairs (Please read the precautions on the back before filling this page). It was prepared from the title compound of Preparation Example 5 3 and 1-methylhexahydropyridine according to the procedure of Example 1. It was a white solid (83%). Elemental analysis: 値: C, 5 7 · 0 2; Η, 6 · 30; N, 16 · 28. C28H37N7〇5S; 0.30H2O calculated C, 56.99; H, 6.59; N, 16.61%. (5 (CDC 1 3): 1.00 (3H, t), 1 · 17 (3 H, t), this paper size applies to China National Standard (CNS) A4 specification (210X297 mm) Γβΐ: ^ 524805 A7 ____B7 __ V. Description of the invention (59) 1 · 8 3 (2 Η, m), 2 · 〇 4 (2 Η, m), 2 · 2 5 (3 Η, s), 2 · 3 2 (3 Η, s ), 2 · 5 0 (7 Η, m), 2 ·· 9 0 (2 Η, t), 3 · 0 9 (4 Η, m), 4 · 2 5 (2 Η, t), 5 · 5 2 (2 Η, s), 7 · 1 4 (1 Η, d), 7 · 8 3 (1 Η, d), 8 · 8 4 (1 Η, s), 10.86 (lH, s) LRMS: m / z 584 (M + 1) +. Example 2 8 Printed by the Consumer Cooperatives of the Central Standard Vehicle Bureau of the Ministry of Economic Affairs 5— {5 — [4 — (2-hydroxyethyl) hexahydropyridine—1 Mono-sulphofluorenyl]-2 -n-propoxyphenyl}-1-1 (3,5-dimethyl iso-slogan slogan -4 -yl) methyl -3 -n-propyl-1,6 -diazo A 7H-pyrazolo [4,3-d] pyrimidin-7-one was prepared from the title compound of Preparation 5 3 and 1- (2-hydroxyethyl) hexahydropyridine according to the procedure of Example 1, White bubble-like (5 7 %) Measured by elemental analysis 値 ·· C, 5 6 · 3 3; Η, 6 · 4 2; N, -62- (Please read the precautions on the back before filling this page) This paper size applies Chinese national standards ( CNS) A4 specification (210X297 mm) 524805 A7 B7 __ V. Description of the invention (60) 15.69 ° C29H39N7〇6S Calculate 値 C, 56.75; H, 6.41; N, 15.98%. 5 (CDCl3): 1.01 ( 3H, t), 1 · 2 0 (3 Η, t), 1 · 8 6 (2 Η, m), 2 · 0 6 (2 Η, m), 2 · 2 8 (1 Η, s), 2.36 (3H, s), 2 · 5 2 (3 Η, s), 2. 5 6 (2 Η, t), 2 · 6 2 (4 Η, m), 2 · 9 2 (2 Η, t), 3 · 1 0 (4 Η, m), 3 · 5 8 (2 Η,. M), 4 · 2 8 (2 Η, t), 5 · 5 5 (2 Η, s), 7 · 1 8 ( 1 Η, d), printed by the Consumer Cooperatives of the Central Standards Bureau of the Ministry of Economic Affairs (please read the precautions on the back before filling out this page) 7 · 8 6 (1 Η, d), 8 · 8 5 (1 Η, s) , 10.88 (lH, s) ° LRMS: m / z 614 (M + 1) +. Example 2 9 5 — [2 —Ethoxyl 5 — (4-methylhexa port ratio 1—Basic paper size applies to China National Standard (CNS) A4 specification (210X 297 mm) _ 63 _ 524805 A7 B7 V. Description of the invention (61) Sulfonyl) phenyl] -3-methyl-1 1- (3,5-dimethylisoimidazole 4-yl) methyl-1,6-dihydro-7H —Pyrazolo [4, 3-d] pyridine-7-one was prepared from the title compound of Preparation Example 5 4 and 1-methylhexahydropyridine according to the procedure of Example 1 as a white solid (8 8 %). Elemental analysis: 値 ·· C, 5 4 · 3 3; Η, 5 · 7 2; N, 1 7.74. ; 0. IOCH2CI2 Calculate 値 C, 54.80; H, 5.72; N, 17.82%. 5 (CDC 1 3): 1.65 (3H, t), 2 · 2 7 (3 Η, s), 2 · 3 2 (3 Η, s), 2.50 (1 OH, m), 3 · 1 2 (4 H; m), 4 · 3 8 (2 H, Q), 5.52 (2H, s),, 7 · 16 (1 H, d), printed by the Consumer Cooperatives of the Central Standards Bureau of the Ministry of Economic Affairs (please read the back first) For the matters needing attention, fill in this page again) 7 · 8 4 (1 H, d), 8 · 8 8 (1 H, s), 10.85 (lH, s). L R M S: m / z 542 (M + 1) +. Example 3 05 — [5 — (4-methylhexahydropyridine-1 1 sulfosulfenyl) —a paper size applicable to the Chinese National Standard (CNS) A4 specification (210X 297 mm) -64- 524805 A7 B7 V. Description of the invention (62) (Please read the precautions on the back before filling in this page) 2 -n-propoxyphenyl] -1-1 (2-methylthiazole- 4-yl) methyl- 3- N-propyl-1,6-dihydro-7H-pyrazolo [4,3-d] pyrimidin-7-one was prepared from the title compound of Preparation 5 6 and 1-methylhexahydropyridine according to Example 1 It was obtained in the step and was white foamy (61%). Elemental analysis: 値: C, 5 5 · 5 1; Η, 6 · 1 2; N, 16.28 ° C 27H35N7〇4S2 Calculate 値 C, 55.36; H, 6.02; N, 16.74%. 5 (CDCl3): 1.0 (3H, t), 1 · 18 (3 Η, t), 1 · 8 6 (2 Η, m), 2 · 〇4 (2 Η, m), 2 · 2 8 (3 Η, s), 2 · 5 0 (4 Η; m), 2 · 6 8 (3 Η, s), 2 · 9 7 (2 Η, t), 3 · 1 2 (4 Η, m), printed by the Consumer Cooperative of the Central Standards Bureau of the Ministry of Economic Affairs 4 • 2 6 (2 Η, t), 5.8 8 (2 Η, S), 6 • 8 8 (1 Η, S), 7.1 7 (1 Η, d), 7 • 8 4 (1 Η, d), 8 • 8 8 (1 Η, s), 10 · 9 〇 (1 Η > s) -65- This paper size applies to China National Standard (CNS) A4 specification (210X297 mm) 524805 A7 B7 V. Description of invention (63) LRMS: m / z 586 (M + 1) +. Example 3 1 5 — [5 — (4-methylhexahydropyridine-1—1-sulfosulfanyl) —2-n-propoxyphenyl] —1— (1-methyl-1, 2, 4— Two-seater —5 —yl) methyl — 3 —n-propyl — 1, 6 —dihydro — 7H — pyrazolo [4,3-d] pyrimidine — 7 -one from the title compound of Preparation Example 5 9 and 1-Methylhexahydropyridine was prepared according to the procedure of Example 1 as a white solid (49%). Elemental analysis: 値: C, 5 4 · 9 6; Η, 6 · 3 8; N, 21 · 17. C26H35N9004S calculation 値 C, 54.82; H, 6.19; N, 22.13%. 5 (CDCl3): 1.01 (3H, t), 1.2 〇 (3 Η,. T), 1.86 (2H, m), 2 〇6 (2 H, m), 2 · 3 ◦ ( 3 H, s), printed by the Consumer Cooperatives of the Central Standards Bureau of the Ministry of Economic Affairs (please read the notes on the back before filling out this page) 2 · 5 〇 (4 H, m), 2 · 9 4 (2 H, t) , 3 · 1 2 (4 H, m), 4 · 0 1 (3 H, s), 4 · 2 7 (2 H, t), 5 · 9 7 (2 H, s), 7 · 1 6 ( 1 H, d), this paper size applies Chinese National Standard (CNS) A4 specification (210X297 mm) _ 66-524805 A7 B7 V. Description of invention (64) 7 · 8 4 (1 Η, s), 7 · 8 6 (1 Η, d), (Read the precautions on the back before filling this page) 8 · 8 5 (1 Η, s), 10.96 (lH, s). LRMS: m / z 570 (M + 1) +. Example 3 2 5— {5 — [4-((2-hydroxyethyl) hexahydropyridine-1—1-sulfofluorenyl] —2-n-propoxyphenyl}} — 1— (1—methyl-1 2,4,4-triazol-5-yl) methyl-1,3-n-propyl-1,6-dihydro-7, pyrene-pyrazolo [4,3-d] pyrimidin-7-one, Preparation Example 59 The title compound and 1- (2-hydroxyethyl) hexahydropyridine were prepared in accordance with the procedures of Example 1 and showed a white foam (62%). · Elemental analysis: 实: C, 5 2. 9 6 Η, 6 · 4 0; N, 20 · 14; C27H37N9〇5S; 〇0.7〇H2〇 Calculate 印 Printed by the Consumers' Cooperative of the Central Standards Bureau of the Ministry of Economic Affairs 6 3HHHHHH 91322124 • c / l \ rv / l \ r \ / (V 2D056051 5C280356 c 5 112222 Ν 2 3 6 Η% 9 5 ο 2 Η 3 ο 〇mm \) / \) / \) / \) ystm This paper size applies to China National Standard (CNS) A4 specification (210X 297 mm) · 67-524805 A7 B7 V. Description of the invention ( 65) 2 · 9 4 (2 Η, t), 3 · 1 2 (4 Η, m), 3 · 5 8 (2 Η, m), 4 · 〇 (3 Η, s), 4 · 3 Ο (2 Η, t), 5 · 9 7 (2 Η, s), 7 · 1 8 (1 Η, s), 7 · 8 2 (1 Η, s), 7 · 8 5 (1 Η, d) , 8.85 (1 Η, s), 10.98 (1H, s) ° LR M S: m / z 60 (M + 1) +. Example 3 3 'Printed by the Consumer Cooperative of the Central Bureau of Standards of the Ministry of Economic Affairs (Read the precautions on the back before filling this page) 5 — [5— -2 -n-propoxyphenyl]-1-(1-methyl-1, 2, 4, 4-5 -yl) methyl-3-n-propyl-1, 6--M-7H- Orbitazol [4,3-d] pyrimidin-7-one_ was prepared from the title compound of Preparation Example 5 9 and 1-ethylhexahydropyridine according to the procedure of Example 1 as a white solid (40% ). Elemental analysis: 値: C, 5 5 · 31; Η, 6.60; N, 21.〇9 ° C 27H37N9004S Calculate 値 C, 55.56; Η, 6.39; N, 21.60%. 5 (CDC 1 3): 1.02 (6H, m), this paper size is applicable to China National Standard (CNS) A4 (210X 297 mm) -68- 524805 A7 B7 V. Description of the invention (66) 1 · 1 8 (3 Η, t), 1 · 8 6 (2 Η, m), 2 · 〇6 (2 Η, m), 2 · 4 1 (2 Η, q), 2 · 5 5 (4 Η , M), 2 · 9 4 (2 Η, t), 3.1〇 (4H, m), 4 · 〇 (3 H, s), 4 · 2 6 (2 H, t), 5 · 9 7 ( 2 H, s), 7.16 (lH, d), 7 · 8 3 (1 H, s), 7 · 8 5 (1 H, d), 8 · 8 4 (1 H,. S), 10.96 (lH , S). L R M S: m / z 584 (M + 1) +. Printed by the Consumer Cooperatives of the Central Standards Bureau of the Ministry of Economic Affairs (please read the precautions on the back before filling this page) Example 3 4 5— {5 — [4 一 (2-methoxyethyl) hexahydroorphine-1 1-sulfofluorenyl]-2 -n-propoxyphenyl} 1 -1 (1 -methyl-1,2,4 -triazol 5 -yl) methyl -3 -n-propyl-1,6 di Hydrogen — 7 Η — 嗤 嗤 [4, 3 — d] H 定 定 定 7 7 7 7 由 由 由 由 由 制备 the title compound of Preparation Example 5 9 and 1-(2-methoxyethyl) hexahydropyridine according to Example 1 It is obtained as a white solid (43%) in this step. The paper size is in accordance with Chinese National Standard (CNS) A4 (210X297 mm) -69-524805 kl B7 V. Description of the invention (67) 〇c? (CDCl3): l .〇〇 (3H, t), 1 · 2 0 (3 Η, t), 1 · 8 6 (2 Η, m), 2 · Ο 6 (2 Η, m), 2 · 5 7 (6 Η, m), 2 · 9 2 (2 Η, t), 3 · 1 2 (4 Η, m), 3 · 3 Ο (3 Η, s), 3 · 4 4 (2 Η, t), 4 · 〇 〇 (3 Η, s), 4 · 2 8 (2 Η, t), 5.9 8 (2 Η, s), 7 · 1 6 (1 Η,. D), 7.8 3 (1 Η, s), 7.85 (l H, d), 8 · 86 (1 1, s), printed by the Consumer Cooperatives of the Central Bureau of Standards of the Ministry of Economic Affairs 10.95 (1Η, s). LRMS: m / z 614 (M + 1) +. Example 3 5 1- [1- (2-methoxyethyl) -1,2,4-triamidine-a 5-yl] methyl-1 5- [5- (4-methylhexahydropyridine) 1 monosulfofluorenyl) —2 —n-propoxyphenyl] —3—n-propyl—1,6—di-70— (Please read the precautions on the back before filling this page) This paper size is applicable to China Standard (CNS) A4 specification (210X297 mm) 524805 A7 B7 V. Description of the invention (68) Hydrogen-7H-pyrazolo [4,3 — d] pyrimidin-7-one (Read the precautions on the back before reading (Fill in this page) Prepared from the title compound of Preparation 64 and 1-methylhexahydropyridine according to the procedure of Example 1. It was white foamy (77%). 5 (CDC 1 3): 0.97 (3 H ^ t), 1 · 16 (3 Η, t), 1 · 8 2 (2 Η, m), 2 · 〇 0 (2 Η, m) , 2 · 2 4 (3 Η, s), 2 · 4 6 (4 Η, m), 2.86 (2H, t),. 3 · 2 5 (3 Η, s), 3 · 6 6 (2 Η, t), 4 · 2 2 (2 Η, t), 4 · 5 2 (2 Η,. t), 5 · 9 7 (2 Η, s), 7 · 1 2 (1 Η, d), 7 · 80 (2 Η, m), printed by the Consumer Cooperatives of the Central Bureau of Standards of the Ministry of Economic Affairs ^ 8 · 8 2 (1 Η, s), 10.86 (lH, s). LRMS: m / z 614 (M + 1) +. Example 3 6 5 — [5 — (4-ethylhexazine 1: 1 ratio 1 to 1 1 base expansion base) 1 2 —n-propoxyphenyl] 1 1 [1 1 (2-methoxyethyl Base) -1, this paper size applies Chinese National Standard (CNS) A4 specifications (210X 297 mm) -71-524805 A7 B7 V. Description of the invention (69) 2,4-triazole-5 -yl] methyl A 3-n-propyl-1,6-dihydro-7H-pyrazolo [4,3-d] pyrimidin-7-one was prepared from the title compound of Preparation Example 4 and 1-ethylhexahydropyridine It was obtained by the procedure of Example 1 and was white foamy (66%). Elementary analysis: 値: C, 5 5.10;;, 6.62; N, ig. YliCzgHnNgOsS Calculate 値 C, 55.49; H, 6.58; N, 20.08%. 5 (CDC 1 3): 0.98 (6H, m), 1.15 (3H, t), 1.81 (2H, m), 2.0.0 (2H, m), 2 · 3 7 (2 H, q), 2 · 5 0 (4 H, m), 2 · 9 0 (2 H, · t), 3 · 0 8 (4 H, m), 3 · 2 6 (3 H, s), 3. 6 8 (2 H, t), 4 · 2 2 (2 H, t), printed by the Consumer Cooperatives of the Central Bureau of Standards of the Ministry of Economic Affairs (please read the precautions on the back before filling this page) 4 · 6 2 (2 H, t), 5 · 9 6 (2 H, s), 7 · 1 2 (1 H, d), 7 · 8 〇 (2 H, m), 8 · 8 2 (1 H, s), 10.86 (lH, s) ° This paper size applies to Chinese National Standard (CNS) A4 specification (210X 297 mm) -72-524805 A7 B7 V. Description of the invention (70) LRMS: m / z 628 (M + 1) +. Example 3 7 5 — [5- (4-Ethylhexahydropyridin-1-ylsulfonyl) —2-n-propoxyphenyl] —1— (4-methyl—1,2,4— Triazol-3-yl) methyl-1,3-n-propyl-1,6-dioxo-7H-D, pyrazolo [4,3-d] pyrimidin-7-one, from the title compound of Preparation 6 and 6 1-Ethylhexahydropyridine was prepared according to the procedure of Example 1 as a white solid (43%). Elemental analysis: 値 ·· C, 5 4 · 4 6; Η, 6 · 3 1; N, 21 · 08. C27H37N9〇4S; 60.20. Calculated. C, 54.54; H, 6.47; N, 21.2%. 5 (CDC 1 3): 1.0 (6H, m), 1 · 2 0 (3 H, .t), 1 · 8 4 (2 H, m), 2 · 0 6 (2 H, m) , 2 · 4 0 (2 H, d), printed by the Consumer Cooperatives of the Central Standards Bureau of the Ministry of Economic Affairs (read the precautions on the back before filling out this page) 2.56 (4H, m), 2 · 9 2 (2 H , T), 3. 1 2 (4 H, m), 3 · 7 6 (3 H, s), 4. 2 8 (2 H, t), 6 · 0 4 (2 H, s), 7 · 1 7 (1 H, d), this paper size applies the Chinese National Standard (CNS) A4 specification (21 × 297 mm) -73 _ 524805 A7 B7 V. Description of the invention (71) 7 · 8 6 (1 Η, d), 8 · 10 (1 Η, s), 8 · 8 6 (1 Η, s), 10.96 (lH, s) ° LRMS: m / z 584 (M + 1) +. Example 3 8 5 — [5 — (4-methylhexazine-co-1-mineral acid group) —2-n-propoxyphenyl] —1— (4—methyl—1,2,4— Triazol-5-yl) methyl-1, 3-n-propyl-1, 6-, chloro-7H, oripazolo [4,3-d] pyrimidin-7-one, from the title compound of Preparation 6 and 6 1-Methylhexahydropyridine was prepared according to the procedure of Example 1 as a white solid (51%). Elemental analysis: 値: C, 5 3 · 0 7; Η, 6 · 1 4; N, 20 · 48. C26H35N9〇4S; 0 · 8 0 Η 2 〇; 〇 10CH2C12; 0 · 05CH3 〇 Calculate 値 C, 52.86; H, 6.30; N, 21.20%. Printed by the Consumer Cooperatives of the Central Standards Bureau of the Ministry of Economic Affairs (please read the precautions on the back before filling out this page) 5 (CDC 1 3): 1.0 × (3H, t), 1 · 2〇 (3H, t ), 1 · 8 2 (2 H, t), 2 · 0 6 (2 H, m), 2 · 2 8 (3 H, s), 2 · 5 0 (4 H, m), 2 · 9 2 (2 H, t), this paper size applies the Chinese National Standard (CNS) A4 specification (210X297 mm) _ 74-524805 A7 B7 V. Description of the invention (72) 3 · 1 0 (4 Η, m), 3 · 7 5 (3 Η, s), 4 · 2 7 (2 Η, t), 6 · 〇 4 (2 Η, s), 7 · 1 6 (1 Η, d), 7 · 8 4 (1 Η, s), 7.86 (lH, d), 8 · 8 4 (1 H, s), 10 · 9 6 (1 H, s). LRMS: m / z 57 ° (M + 1) +. Example 3 9 5 — {5 — [4 — (2-hydroxyethyl) hexahydropyridine-1 1-sulfosulfanyl] -1 2-n-propoxyphenyl}} 1 1 (4 1 methyl-1 1 1,2,4-triazol-5-yl) methyl-3-n-propyl-1,6-dihydro-7H-pyrrolo [4,3-d] Chevidine-7-ketone Central Printed by the Bureau of Standards, Consumer Cooperative ¾ From the title compound of Preparation 66 and 1- (2-hydroxyethyl) hexahydropyridine according to the procedure of Example 1, a white solid (37%). Measured by elemental analysis. : C, 5 3 · 4 9; H, 6 · 0 4; N, 21.5. C27H37N9O5S; 0. 10H2O calculated C, 53.91; H, 6.23; N, 20.96%. 5 (CDC 1 3): 1.0 (3Ii, t), 1 · 2 0 (3 H, t), 1 · 8 4 (2 H, m), -75- (Read the precautions on the back before reading (Fill in this page again) This paper size is in accordance with Chinese National Standard (CNS) A4 specification (210X 297 mm) 524805 A7 B7 Printed by the Consumer Cooperatives of the Central Standards Bureau of the Ministry of Economy , M), 2 · 2 8 (1 Η, s), 2 · 5 6 (2 Η, t), 2 · 6 4 (4 Η, m), 2 · 9 2 (2 Η, t), 3. 1 4 (4 Η, m), 3 · 5 8 (2 Η, m), 3 · 7 7 (3 Η, s), 4 · 2 8 (2 Η, t), 6 · 〇 2 (2 Η, s), 7 · 1 8 (1 Η, d), 7 · 8 6 (1 Η, d), 8 · 1 〇 (1 Η, s), 8 · 8 6 (1 Η, s), 1 〇 · 9 8 (1 Η, s). LRMS: m / z 6 0 '0 (M + 1) +. Example 4 Ο 5 — [5— (4-methylhexahydropyridine—1-sulfosulfanyl) —2-n-propoxyphenyl] -1- (1,2,4-oxadiazol-3 -Methyl) methyl-1,3-n-propyl-1,6-dihydro-1,7Η-pyrazolo [4,3-d] ann-7-one, from the title compound of Preparation Example 7 and 1-methyl Hexahydropyridine was prepared according to the procedure of Example 1 as a solid (33%). (Please read the precautions on the back before filling out this page) This paper size applies to Chinese National Standard (CNS) A4 gauge (21〇'297 mm) -76-524805 A7 B7 V. Description of the invention (74) 5 (CDCl3): 1.0 (3H, t), 1 · 1 8 (3 Η, t), 1 · 8 7 (2 Η, m), 2 · 〇 4 (2 Η, m), 2 · 2 8 (3 Η, s), 2 · 5 Ο (4 Η, m), 2 · 9 4 (2 Η, t), 3 · 1 2 (4 Η, m), 4. 2 6 (2 Η, t ), 6 · Ο 2 (2 Η, s), 7 · 1 7 (1 Η, d), 7 · 8 5 (1 Η, d), 8 · 6 7 (1 Η, s), 8 · 8 8 (1 μm, s), 10.96 (lH, s) ° LRMS: m / z 557 (M + 1) +. Example 4 1 Printed by the Consumer Cooperatives of the Central Bureau of Standards of the Ministry of Economic Affairs (read the precautions on the back before filling out this page) 1 1; base 5 — [2 — ethoxyl 5 — (4-methylhexahydro Gengyi 1-based mineral group) Phenyl] -3-n-propyl-1,6-dihydro-7H-pyrazolo [4,3-d] pyrimidin-7-one The title compound of Example 86 will be prepared (5 · Og, 8.8 mmo 1) Add to a stirred solution containing potassium tertiary butoxide (1.2 g, 10 mmo 1) and tertiary butanol (75ml), and make this paper standard applicable to China Standard (CNS) A4 gauge (210X297 mm) -77-524805 A7 B7 V. Description of the invention (75) The mixture was heated under reflux for 20 hours, and then cooled and evaporated under reduced pressure. The obtained residue was partitioned between ethyl acetate (300 ml) and water (300 ml), and the separated aqueous phase portion was extracted with ethyl acetate (3 × 1 50 m 1). After being combined, the organic solution was washed successively with water (150 m 1) and brine (150 m 1), dried (Mg S04), and evaporated under reduced pressure to obtain a white solid. The white solid was subjected to ether Trituration and drying under vacuum gave the title compound (4.29 g) as white fine crystals. Elemental analysis: 値: C, 6 0 · 8 4; Η, 6 · 2 0; N, 15 · 08. C28H34N6〇4S calculates 値 C, 61.08; Η, 6.22; N, 15.26%. 5 (CDC 1 3): 1 · 〇1 (3 Η, t), 1.64 (3H, t), 1 · 8 8 (2 H, m), 2 · 2 6 (3 H, s), 2 · 4 8 (4 H, m), 2 · 9 6 (2 H, t), 3 · 1 2 (4 H, m), printed by the Consumer Cooperatives of the Central Standards Bureau of the Ministry of Economic Affairs (read the precautions on the back before filling This page) 4 · 3 8 (2 H, q), 5 · 7 8 (2 H, s), 7.14 (lH, d), 7 · 2 6 (3 H, m), 7 · 4 0 (2 H , M), 7 · 8 2 (1 H, d), this paper size applies Chinese National Standard (CNS) A4 Regulation (210X 297 mm). 78-524805 A7 B7 Printed by the Consumers' Cooperative of the Central Standards Bureau of the Ministry of Economic Affairs System five, description of the invention (76) 8 · 8 4 (1 Η, s), 10.8 0 (lH, s). LRMS: m / z 551 (M + l) +. Example 4 2 1 One-Cyclo-5— [5- — (4-methylhexahydro / co-coated 1-based fluorenyl) -2—n-propoxyphenyl] -3—n-propyl-1 ′ 6-dihydro-7 pyrene-pyrido [4,3-d] pyrimidin-7-one A 60% w / w suspension of sodium hydride ('160 mg, 4 mm ο 1 in mineral oil) Add 1-propanol (20 m 1) under ice cooling and stirring in portions, and when the effervescence ceases, add the title compound (5 5 Omg, lmmo 1) of Example 41. The resulting mixture was heated at reflux for 96 hours, allowed to cool and evaporated under reduced pressure. The residue was partitioned between ethyl acetate (50 ml) and water (50 ml), and the separated aqueous phase was then extracted with ethyl acetate (total 100 m 1). The organic phase was combined and dried (Na S0 4), evaporated under reduced pressure, and the residue was purified by column chromatography on silica gel. The eluent used was ethyl acetate: methanol: 0 · 880 aqueous ammonia (95: 5: 0.5) gave the title compound (230 mg) as a colorless foam. Elemental analysis: 値: C, 6 1 · 6 5; Η, 6 · 4 8; N, 14 · 53. C29H36N6〇4S calculated 値 C, 61 · 68; Η, 6.48; N, 14.88%. 5 (CDC 1 3): 0.98 (3H, t), this paper size is applicable to Chinese National Standard (CNS) A4 gauge (210X 297 cm) -79-(Please read the precautions on the back before filling out this page 4 524805 A7 B7 V. Description of the invention (77) 1 · 1 5 (3 Η, t), 1.83 (2H, m), 2 · Ο 1 (2 Η, m), 2 · 2 4 (3 Η, s), 2 · 4 6 (4 Η, m), 2 · 9 2 (2 Η, t), 3 · 008 (4 Η, m), 4 · 2 2 (2 Η, t), 5. 7 3 (2 Η , S), 7 · 1 2 (1 Η, d), 7 · 2 7 (3 Η, m), 7 · 3 6 (2 Η, m), 7 · 8 Ο (1 Η, d); 8 · 8 2 (1 Η, s), 1 1 · 8 4 (1 Η, s). LRMS: m / z 565 (Μ + 1) +. Printed by the Consumer Cooperative of the Central Standards Bureau of the Ministry of Economic Affairs (please read the first Please fill in this page again for attention) Example 4 3 1- (4-chlorobenzyl) -5— [5— (4-methylhexahydro-1,1-sulfosulfanyl) -2-n-propoxybenzene Group] -3-n-propyl-1,6-dihydro-7H-pyrazolo [4,3-d] pyrimidin-7-one was prepared from the title compound of Preparation 8 7 and 1-methylhexahydropyridine Follow the steps in Example 1 Manufactured as a white solid (75%). This paper is scaled to the Chinese National Standard (CNS) A4 (210X 297 mm) -80- Printed by the Consumers' Cooperative of the Central Standards Bureau of the Ministry of Economic Affairs 524805 A 7 B7 V. Invention Explanation (78) Observed and measured 兀: C, 5 7 · 9 9; Η, 5. 9 4; N, 13 · 76. C29H35C1N6〇4S Calculate 値 C, 58.14; H, 5.89; N, 14.03 %. 5 (CDCl3): 1.0 (3H, t), 1 · 19 (3 Η, t), 1 · 8 6 (2 Η, m), 2 · Ο 6 (2 Η, m), 2 · 2 8 (3 Η, s), 2 · 4 8 (4 Η, m), 2 · 9 4 (2 Η, t), 3. 〇 8 (4 Η, m), 4 · 2 4 (2 Η, t), 5 · 7 2 (2 Η, s), 7 · 1 5 (1 Η, d), 7 · 2 6 (2 Η, d), 7 · 3 4 (2 Η, d), 7 · 8 2 (1 Η, d), 8 · 8 4 (1 Η, s), 1 0. 9 〇 (1 Η ^ s) ° LR M S: m / ζ 599 (M + 1) +. Example 4 4 1— (4-Chlorodryl) —5— [2-Ethoxy-5— (4-methylhexanaphthyl-1, 1-based acid expanding group) —Phenyl] -3—n-propyl The basic paper size applies the Chinese National Standard (CNS) A4 Orange (210X 297 mm) -81-(Please read the precautions on the back before filling this page), \ 呑 524805 A7 B7 V. Description of the invention (79 Printed by the Consumer Cooperatives of the Central Standards Bureau of the Ministry of Economic Affairs (please read the precautions on the back before filling this page)

酮 施 元 1 C 5 2 2Ketone dosing 1 C 5 2 2

4 5 7 7 7 7 8 1 L 6 —二氫—7H —吡唑並〔4，3 — d〕嘧啶—7 —4 5 7 7 7 7 8 1 L 6 —dihydro-7H —pyrazolo [4,3 — d] pyrimidine-7 —

由製 例1之 素分析 4 . 3 ，5 7 (CD .6 6 .8 4 .3 6 .6 0 .9 2 .18 .3 6 .7 2 .14 .2 4 .34 .8 2 .8 4 0 . 8 RMS 備例8 8之標題化合物及1 -甲基六氫吡哄依實 步驟製得，呈白色晶狀固體（2 7 % )。 實測値 0。C ; .4 7 C 1 3 ) (3 Η (2 Η (3 Η (4 Η (2 Η (4 Η (2 Η (2 Η (1 Η (2 Η (2 Η (1 Η (1 Η m ) s ) m ) t ) m ) Q ) s ) d ) d ) d ) d ) s ) 丨 7·43;Η，5·67 C 1 N 6〇4 S計算値 丨·68;Ν，14·36%。 〇 0 ( 3 Η ， t )， 6 ( 1 Η，s )。 :m/z 5 8 5 ( Μ + 1 ) 本紙張尺度適用中國國家標準（CNS ) Α4規枱（210Χ 297公釐）-82 -From the prime analysis of Preparation Example 4, 3, 5 7 (CD .6 6 .8 4 .3 6 .6 0 .9 2 .18 .3 6 .7 2 .14 .2 4 .34 .8 2 .8 4 0.8 RMS The title compound of Preparation Example 8 and 1-methylhexahydropyridine were prepared according to the actual procedures as a white crystalline solid (27%). Found 値 0.C; .4 7 C 1 3 ) (3 Η (2 Η (3 Η (4 Η (2 Η (4 Η (2 Η (2 Η (1 Η (1 Η m) s) m) t) m) Q) s) d) d) d) d) s) 丨 7 · 43; Η, 5.67 C 1 N 6〇4 S calculation 値 丨 · 68; N, 14.36%. 〇0 (3 ，, t), 6 (1 Η, s): m / z 5 8 5 (Μ + 1) This paper size is applicable to China National Standard (CNS) Α4 gauge (210 × 297 mm) -82-

N 524805 A7 B7 五、發明説明（80 ) 實施例4 5 1— (4 —氯苄基）一5 — {2 —乙氧一5 —〔4 — (2 —羥乙基）六氫吡哄一 1 一基磺醯基〕苯基} 一 3 — 正丙基—1，6 -二氫—7H —吡唑並〔4，3 - d〕嘧 D定一 7 —酮 由製備例8 8之標題化合物及1 — ( 2 -羥乙基）六 氫吡畊依實施例1之步驟製得，呈白色晶狀固體（6 8 % )° 元素分析實測値：C，5 6 · 6 0 ; Η，5 · 7 1 ; N， 1 3 · 47。C29H35C 1 N6〇5S 計算値 (請先閱讀背面之注意事項再填寫本頁) 經濟部中央標準局員工消費合作社印製 2 3HH HHHHHHHHHH 61323424222122 • ^#0 /IV rv X\ /V v、 y\ '\ /(V rv rv rv rv 6D462228082865 5C687892727123 ， /—vv ···········# C5112223345777 N 3 7 5 Η % 6 6 3 \)y \)/ \)y \ly \)/t m m m t m m Q s d d d Η 3 /|\ ο ο 本纸張尺度適用中國國家標準（CNS ) A4規枱（210X 297公釐）-83- 524805 A7 B7 .五、發明説明（81 ) 7 · 8 2 ( 1 Η，d )， 8 · 8 2 ( 1 Η，s )， l〇.88(lH，s)° LRMS:m/z 615(M+1) +。 實施例4 6 1— (2 —氰卡基）一5 —〔2 —乙氧一5 — (4 — 甲基六氫哦畊一 1 一基擴醯基）一苯基〕一 3 -正丙基一 1，6 — 二氫一 7H —吡唑並〔4，3 — d〕嘧啶—7-酮 由製備例9 0之標題化合物及1 -甲基六氫吡畊依實 施例1之步驟製得，呈白色粉末（6 0 % )。 元素分析實測値：C，6 0 · 4 2 ; Η，5 · 7 9 ; N， 16.85°C29H33N7〇4S 計算値 經濟部中央標準局員工消費合作社印製 2 2 7 7 7 8 o 3 HHHHHHHH 5132341111 . o rv /l\ /l\ /(\ fv /(\ /iv /(vv 0D50826840 6C69253689 ， y/l\ ········ N 8 7 5 Η % 3 ο 7 m s m m d d s Η 3 /ίν ο ο λι/ \ly (請先閲讀背面之注意事項再填寫本頁)N 524805 A7 B7 V. Description of the invention (80) Example 4 5 1— (4-chlorobenzyl) -5— {2—ethoxy-1 5— [4— (2-hydroxyethyl) hexahydropyridine] 1 monosulfofluorenyl] phenyl} -3-n-propyl-1,6-dihydro-7H-pyrazolo [4,3-d] pyrimidin-7-one by the title of Preparation Example 8 8 The compound and 1- (2-hydroxyethyl) hexahydropyridine were prepared according to the procedure of Example 1. It was a white crystalline solid (68%). Elemental analysis found 値: C, 5 6 · 6 0; Η, 5 · 7 1; N, 1 3 · 47. C29H35C 1 N6〇5S calculation 値 (Please read the notes on the back before filling this page) Printed by the Consumer Cooperatives of the Central Standards Bureau of the Ministry of Economic Affairs 2 3HH HHHHHHHHHHH 61323424222122 • ^ # 0 / IV rv X \ / V v, y \ ' \ / (V rv rv rv rv 6D462228082865 5C687892727123, / —vv ········· # C5112223345777 N 3 7 5 Η% 6 6 3 \) y \) / \) y \ ly \) / tmmmtmm Q sddd Η 3 / | \ ο ο This paper size is applicable to Chinese National Standard (CNS) A4 gauge (210X 297 mm) -83- 524805 A7 B7. V. Description of the invention (81) 7 · 8 2 (1 Η, d), 8 · 82 (1 Η, s), 10.88 (lH, s) ° LRMS: m / z 615 (M + 1) +. Example 4 6 1— (2-Cyanocarboxyl) -5— [2-Ethoxy-5— (4-Methylhexahydroquinone-1—1-based fluorenyl) —phenyl] —3—n-propyl The base 1,6-dihydro-7H-pyrazolo [4,3-d] pyrimidin-7-one was prepared from the title compound of Preparation Example 90 and 1-methylhexahydropyridine according to the procedure of Example 1. Obtained as a white powder (60%). Elemental analysis: 値: C, 6 0 · 4 2; Η, 5 · 7 9; N, 16.85 ° C 29H33N7〇4S calculation 値 printed by the Consumer Cooperatives of the Central Standards Bureau of the Ministry of Economy 2 2 7 7 7 8 o 3 HHHHHHHH 5132341111. o rv / l \ / l \ / (\ fv / (\ / iv / (vv 0D50826840 6C69253689, y / l \ ······· N 8 7 5 Η% 3 ο 7 msmmdds Η 3 / ίν ο ο λι / \ ly (Please read the notes on the back before filling this page)

本紙張尺度適用中國國家標準（CNS ) A4規格（210X 297公釐）-84- 524805 A7 B7 五、發明説明（82) 1 〇· 8 8 ( 1 η ， S )。 L R M S ： m / ζ 576 (Μ+1)+。 實施例4 7 1— (2 —胺鑛节基）一5 —〔2 —乙氧—5— (4 —甲基六氫卩比畊—1 一基磺醯基）一苯基〕—3 —正丙基 一 1，6 -二氫—7Η — d 比 π坐並〔4，3 — d〕嘧^定—7 一酮 把2 Μ的氫氧化鈉水溶液（5 m 1 )加入一攪拌中而 含有實施例46之標題化合物（200mg，〇 . 35 m m 〇 1 )的乙醇（5 m 1 )溶液裡，在室溫下攪拌此混 合物3小時，然後減壓蒸發。把得到的殘餘物溶在水（ 1 0 m 1 )裡，再用乙酸乙酯（總量爲5 0 m 1 )對該溶 液進行萃取，有機取萃取液經合倂後乾燥（N a 2 S 0 4 ) ，接著減壓蒸發。以逆向管柱層析法在聚苯乙烯樹脂（ M C I凝膠）上對所得殘餘物進行純化，使用乙腈：水（ 1〇：9 0至4 0 : 6 0 )之沖提梯度，得到的標題化合 物（7 2 m g )呈白色粉末。 經濟部中央標準局員工消費合作社印製 (請先閲讀背面之注意事項再填寫本頁) 元素分析實測値·· C，5 6 · 6 7 ; Η，5 · 7 9 ; N， 16 · 00。C29H35N7〇5S ; Η2〇計算値 C，56.94;H，6.10;N，16.〇3%。 5(DMS〇d6):〇.94(3H，t)， 1 · 3 4 ( 3 Η，t )， 1 . 7 7 ( 2 Η，m )， 本紙張尺度適用中國國家標準（CNS ) Α4規枱（210X 297公釐） 85 - 524805 A7 B7 五、發明説明（83 ) 2 · 1 4 ( 3 Η，s )， 2 · 3 8 ( 4 Η，m )， 2 · 8 〇（2 Η，t )， 2 · 9 2 ( 4 Η，m )， 4 · 2 1 ( 2 Η，q )， 5 · 9 8 ( 2 Η，s )， 6 · 5 9 ( 1 Η，s )， 7 . 3 6 ( 3 Η，m )， 7 · 5 6 ( 2 Η，m )， 7 · 8 2 ( 1 Η，d )， 7 · 9 〇（1 Η，s )， 8 · 0 〇（1 Η，s )， 12.26(lH，s)° 實施例4 8 經濟部中央標準局員工消費合作社印製 (請先閱讀背面之注意事項再填寫本頁) 1— (4 —胺羰苄基）一 5 —〔2 —乙氧—5— (4 一甲基六氣吼哄一 1 一基擴薩基）一苯基〕一 3 —正丙基 —1，6 —二氫—7H — 吡唑並〔4，3 — d〕嘧啶—7 -酮 由製備例9 1之標題化合物及1 -甲基六氫吡畊依實 施例1之步驟製得，呈白色固體（9 3 % )。 元素分析實測値：C，5 8 · 1 7 ; Η，5 · 8 8 ; N， 16.28°C29H35N7〇5S 計算値 C，58.67;H，5.94;N， 16.51%。 本纸張尺度適用中國國家標準（CNS ) A4規枱（210X297公t ) - 86 - 524805 A7 B7 五、發明説明（84 ) 5 ( D M S 0 d 6 ):〇.94(3H，t)， 1 · 3 5 ( 3 Η，t )， 1 · 7 6 ( 2 Η，m )， 2 · 1 5 ( 3 Η，s )， 2 · 3 7 ( 4 Η，m )， 2 · 8 0 ( 2 Η，t )， 2 · 9 2 ( 4 Η，m )， 4 . 2 1 ( 2 Η，q )， 5 · 7 9 ( 2 Η，s )， 7 · 3 〇（3 Η，m )， 7 · 3 9 ( 1 Η，d )， 7 · 8 4 ( 5 Η，m )， 12.29(lH，s)° L R M S ： m / z 594(M+1)+。 實施例4 9 經濟部中央標準局員工消費合作社印製 (請先閱讀背面之注意事項再填寫本頁) 5 —〔2 —乙氧一 5 — (4 —甲基六氫吡畊一 1—基 磺醯基）苯基〕一 1— (2 —硝苄基）一 3 -正丙基一 1 ，6 -二氫—7H —吡唑並〔4，3 — d〕嘧啶—7 —酮 由製備例9 3之標題化合物及1 -甲基六氫吡畊依實 施例1之步驟製得，呈白色粉末（8 8 % )。 元素分析實測値：C，5 6 · 3 7 ; Η，6 · 1 4 ; N， 14. 03。C28H33N7〇6S ； CH3C〇2CHCH3) 2計算値 C，56 · 80 ; 本紙張尺度適用中國國家標準（CNS ) A4規格（210X 297公釐）-87 - 經濟部中央標準局員工消費合作社印製 524805 A7 B7 五、發明説明（85) Η，6·21;Ν，14·05%。 5(CDCl3):l.〇〇(3H，t)， 1 · 6 〇（3 Η，t )， 1 · 8 8 ( 2 Η，m )， 2 · 2 8 ( 3 Η，s )， 2 . 5 2 ( 4 Η，m )， 2 · 9 7 ( 2 Η，t )， 3 · 1 〇（4 Η，m )， 4 · 3 6 ( 2 Η，q )， 6 · 2 4 ( 2 Η，s )， 6 · 7 〇（1 Η，d )， 7 . 1 4 ( 1 Η，d )， 7 · 4 4 ( 2 Η，m )， 7 · 8 4 ( 1 Η，d )， 8 . 1 2 ( 1 Η，d )， 8 · 8 6 ( 1 Η，s )， l〇.90(lH，s)。 LRMS:m/z 596 (M+1)+。 實施例5 0 5— {5 —〔4 — (2 —羥乙基）六氫吡畊一1 一基 磺醯基〕一 2 -正丙氧苯基} 一1一（2 —硝苄基）一 3 一正丙基一 1，6 —二氫—7H —吡唑並〔4，3 — d〕 嘧π定一 7 -酮 本纸張尺度適用中國國家標準（CNS ) A4規桔（21〇Χ；297公釐)~~- 88 -~^ (讀先閱讀背面之注意事項再填寫本頁)This paper size applies Chinese National Standard (CNS) A4 specification (210X 297 mm) -84- 524805 A7 B7 V. Description of the invention (82) 1 0 · 8 8 (1 η, S). L R M S: m / ζ 576 (M + 1) +. Example 4 7 1— (2-Amine Benzyl) —5— [2-Ethoxy-5— (4-methylhexahydropyrene-1—1-sulfofluorenyl) —phenyl] —3— N-propyl-1,6-dihydro-7Η-d than π and [4,3-d] pyrimidine-7-ketone Add 2 M sodium hydroxide aqueous solution (5 m 1) to a stirring and In a solution of the title compound of Example 46 (200 mg, 0.35 mm 〇1) in ethanol (5 ml), the mixture was stirred at room temperature for 3 hours, and then evaporated under reduced pressure. The obtained residue was dissolved in water (10 m 1), and the solution was extracted with ethyl acetate (a total of 50 m 1). The organic extract was combined and dried (N a 2 S 0 4), followed by evaporation under reduced pressure. The obtained residue was purified by reverse column chromatography on polystyrene resin (MCI gel) using an acetonitrile: water (10:90 to 40:60) gradient to obtain the title. Compound (72 mg) was a white powder. Printed by the Consumer Cooperatives of the Central Standards Bureau of the Ministry of Economic Affairs (please read the precautions on the back before filling out this page) Elemental Analysis and Measurement 値 ·· C, 5 6 · 6 7; Η, 5 · 7 9; N, 16 · 00. C29H35N7〇5S; Η20 calculations; C, 56.94; H, 6.10; N, 16.03%. 5 (DMS〇d6): 0.94 (3H, t), 1.34 (3 Η, t), 1. 7 (2 Η, m), this paper size applies Chinese National Standard (CNS) Α4 regulations Taiwan (210X 297 mm) 85-524805 A7 B7 V. Description of the invention (83) 2 · 1 4 (3 Η, s), 2 · 3 8 (4 Η, m), 2 · 8 〇 (2 Η, t ), 2 · 9 2 (4 Η, m), 4 · 2 1 (2 Η, q), 5 · 9 8 (2 Η, s), 6 · 5 9 (1 Η, s), 7. 3 6 (3 Η, m), 7 · 5 6 (2 Η, m), 7 · 8 2 (1 Η, d), 7 · 9 〇 (1 Η, s), 8 · 0 〇 (1 Η, s) , 12.26 (lH, s) ° Example 4 8 Printed by the Consumer Cooperative of the Central Bureau of Standards of the Ministry of Economic Affairs (please read the precautions on the back before filling out this page) 1— (4-aminobenzyl) —5— [2 —Ethoxy—5— (4-methylhexazine-coated 1- 1-dioxanyl) -phenyl] -3-n-propyl-1,6-dihydro-7H —pyrazolo [4,3 — D] Pyrimidin-7-one was prepared from the title compound of Preparation Example 91 and 1-methylhexahydropyridine according to the procedure of Example 1 as a white solid (93%). Elemental analysis: 値: C, 5 8 · 17; Η, 5 · 8 8; N, 16.28 ° C 29H35N7 05S Calculate 値 C, 58.67; H, 5.94; N, 16.51%. This paper size applies Chinese National Standard (CNS) A4 gauge (210X297g t)-86-524805 A7 B7 V. Description of the invention (84) 5 (DMS 0 d 6): 0.94 (3H, t), 1 · 3 5 (3 Η, t), 1 · 7 6 (2 Η, m), 2 · 1 5 (3 Η, m), 2 · 3 7 (4 Η, m), 2 · 8 0 (2 Η , T), 2 · 9 2 (4 Η, m), 4. 2 1 (2 Η, q), 5 · 7 9 (2 Η, s), 7 · 3 〇 (3 Η, m), 7 · 3 9 (1 Η, d), 7 · 8 4 (5 Η, m), 12.29 (lH, s) ° LRMS: m / z 594 (M + 1) +. Example 4 9 Printed by the Consumer Cooperatives of the Central Bureau of Standards of the Ministry of Economic Affairs (please read the precautions on the back before filling out this page) 5 — [2 —Ethoxyl 5 — (4 —Methylhexahydropyridine 1—Base Sulfonyl) phenyl] 1- (2-nitrobenzyl) -3-n-propyl-1,6-dihydro-7H-pyrazolo [4,3-d] pyrimidin-7-one is prepared from The title compound of Example 9 3 and 1-methylhexahydropyridine were prepared according to the procedure of Example 1 as a white powder (88%). Elemental analysis: 値: C, 5 6 · 3 7; Η, 6 · 1 4; N, 14. 03. C28H33N7〇6S; CH3C〇2CHCH3) 2 Calculate 値 C, 56 · 80; This paper size applies to China National Standard (CNS) A4 specification (210X 297 mm) -87-Printed by the Consumers' Cooperative of the Central Standards Bureau of the Ministry of Economic Affairs 524805 A7 B7 V. Description of the invention (85) Η, 6.21; N, 14.05%. 5 (CDCl3): 1.0 (3H, t), 1.6 〇 (3 Η, t), 1. 8 8 (2 Η, m), 2. 2 8 (3 Η, s), 2. 5 2 (4 Η, m), 2 · 9 7 (2 Η, t), 3 · 1 〇 (4 Η, m), 4 · 3 6 (2 Η, q), 6 · 2 4 (2 Η, s), 6 · 7〇 (1 Η, d), 7. 1 4 (1 7, d), 7 · 4 4 (2 Η, m), 7 · 8 4 (1 Η, d), 8.1 2 (1 mm, d), 8 · 86 (1 mm, s), 10.90 (lH, s). LRMS: m / z 596 (M + 1) +. Example 5 0 5— {5 — [4 -— (2-hydroxyethyl) hexahydropyridine-1—1-sulfosulfanyl] —2-n-propoxyphenyl} —1— (2-nitrobenzyl) 1-3 N-propyl-1,6-dihydro-7H-pyrazolo [4,3 — d] Pyridine-1 7-one This paper standard is applicable to Chinese National Standard (CNS) A4 Orange (21〇 Χ; 297mm) ~~-88-~ ^ (Read the precautions on the back before filling in this page)

、1T 經濟部中央標準局員工消費合作社印製 524805 A7 B7 五、發明説明（86 ) 由製備例94之標題化合物及1一（2-羥乙基）六 氫吡畊依實施例1之步驟製得，呈白色晶狀固體（7 6 % )° 元素分析實測値：C，56.15;H，5.83;N， 15.〇6°C3〇H37N7〇7S計算値 C，56.33;H，5.83;N，15.33%。 (5(CDCl3):l.〇4(3H，t); 1，1 7 ( 3 Η，t )， 1 · 9 0 ( 2 Η，m )， 2 · 0 4 ( 2 Η，m )， 2 · 3 〇（1 Η，t )， 2 · 5 7 ( 2 Η，t )， 2 · 6 2 ( 4 Η，m )， 2 · 9 8 ( 2 Η，t )， 3 · 1 2 ( 4 Η，m )， 3 · 5 8 ( 2 Η，m )， 4 · 2 6 ( 2 Η，t )， 6 · 2 4 ( 2 Η，s )， 6 · 6 8 ( 1 Η，d )， 7 · 1 8 ( 1 Η，d )， 7 · 4 6 ( 2 Η，d )， 7 · 8 6 ( 1 Η，d )， 8 · 1 2 ( 1 Η，d )， 8 · 9 〇（1 Η ，s )， 本紙張尺度適用中國國家標準（CNS ) A4規枱（21〇'/297公釐）-89 - (請先閱讀背面之注意事項再填寫本頁 訂 524805 B7 五、發明説明（87 ) l〇.96(lH，s)° L R M S ： m / z 64〇（M+1)+。 實施例5 1 5 —〔2 —乙氧一 5 — (4 —甲基六氫吡畊一 1 一基 擴醯基）苯基〕一 1 一（4 一硝节基）一 3 -正丙基一 1 ，6 -二氫一 7H -吡唑並〔4，3 - d〕嘧啶—7 —酮 由製備例9 5之標題化合物及1 -甲基六氫吡畊依實 施例1之步驟製得，呈灰色固體（6 4 % )。 元素分析實測値：C，5 6 · 1 0 ; Η，5 · 5 5 ; N， 16.01°C28H33N7〇6S 計算値 C，56.46;H，5.58;N，16.46%。 (5(CDCl3):l.〇〇（3H，t)， 1 · 6 6 ( 3 Η，t )， 1 · 8 8 ( 2 Η，m )， 2 · 4 〇（3 Η，s )， 2 · 6 8 ( 4 Η，m )， 2 · 9 6 ( 2 Η，t )， 經濟部中央標準局員工消費合作社印製 (請先閱讀背面之注意事項再填寫本頁) 3 · 2 4 ( 4 Η，m )， 4 · 3 7 ( 2 Η，Q )， 5 · 8 4 ( 2 Η，s )， 7 · 1 6 ( 1 Η，d )， 7 . 5 2 ( 2 Η，d )， 7 · 8 2 ( 1 Η，d )， 本纸張尺度適用中國國家標準（CNS ) A4規枱（210X 297公釐）-90 - 經濟部中央標準局員工消費合作社印製 524805 A7 B7 __ 五、發明説明（88 ) 8 · 1 6 ( 1 Η，s )， 8 · 1 8 ( 2 Η，d )， 10.92(lH，s)。 實施例5 2 1 一（2 —胺苄基）一5 —〔2 —乙氧一5 —（4 一 甲基六氫吡畊—1 一基磺醯基）苯基〕一3 —正丙基一 1 ，6 -二氫一 7H —吡唑並〔4，3 — d〕嘧啶—7 —酮 把藍尼鎳觸媒（Raney nickel catalyst，3 0 〇 m g ) 加入實施例4 9標題化合物（置於4 0 m 1甲醇裡）的攪 拌懸浮液裡，令此混合物在3 4 5 k P a ( 5 0 P s i ) 及5 0 °C下氫化2 0小時，然後冷卻並過濾。濾片用甲醇 (5 0 m 1 )洗過，甲醇溶液合倂後減壓蒸發。所得殘餘 物以管柱層析法利用二氯甲烷：甲醇（9 5 : 5 )爲沖提 液在矽膠上進行純化，然後由乙酸乙酯結晶化而得到呈白 色粉末的標題化合物（190mg)。 元素分析實測値：C，5 8 · 9 8 ; Η，6 · 2 0 ; N， 17· 25。C28H35N7〇4S 計算値 C，59.45;H，6.24;N，17.33%。 5 ( C D C 1 3 ) :l.〇〇(3H，t)， 1 · 6 4 ( 3 Η，t )， 1 · 8 3 ( 2 Η，m )， 2 · 2 7 ( 3 Η，s )， 2 · 4 8 ( 4 Η，m )，Printed by the Consumer Cooperative of the Central Standards Bureau of the Ministry of Economic Affairs, 1T 524805 A7 B7 V. Description of the Invention (86) The title compound of Preparation Example 94 and 1- (2-hydroxyethyl) hexahydropyridine were prepared according to the steps of Example 1. Obtained as a white crystalline solid (76%) ° Elemental analysis: 値: C, 56.15; H, 5.83; N, 15.〇6 ° C 〇H37N7〇7S Calculate 値 C, 56.33; H, 5.83; N, 15.33%. (5 (CDCl3): 1.04 (3H, t); 1,7 (3 Η, t), 1 · 9 0 (2 Η, m), 2 · 0 4 (2 Η, m), 2 · 3 〇 (1 Η, t), 2 · 5 7 (2 Η, t), 2 · 6 2 (4 Η, m), 2 · 9 8 (2 Η, t), 3 · 1 2 (4 Η , M), 3 · 5 8 (2 Η, m), 4 · 2 6 (2 Η, t), 6 · 2 4 (2 Η, s), 6 · 6 8 (1 Η, d), 7 · 1 8 (1 Η, d), 7 · 4 6 (2 Η, d), 7 · 8 6 (1 Η, d), 8 · 1 2 (1 Η, d), 8 · 9 〇 (1 Η, s), this paper size applies the Chinese National Standard (CNS) A4 gauge (21〇 '/ 297 mm) -89-(Please read the precautions on the back before filling out this page to order 524805 B7 V. Description of the invention (87) lO.96 (lH, s) ° LRMS: m / z 64〇 (M + 1) +. Example 5 1 5 — [2 —Ethoxyl 5 — (4-methylhexahydropyridine) 1 1 Sulfanyl) phenyl] -1 1- (4-nitrobenzyl) -3-n-propyl-1,6-dihydro-7H-pyrazolo [4,3-d] pyrimidin-7-one The title compound of Preparation 9 5 and 1-methylhexahydropyridine were prepared according to the procedures of Example 1 as a gray solid. 6 4%). Elementary analysis: ，: C, 5 6 · 10; Η, 5 · 5 5; N, 16.01 ° C28H33N7〇6S Calculate 値 C, 56.46; H, 5.58; N, 16.46%. (5 ( CDCl3): 1.0 (3H, t), 1.6 (6 Η, t), 1.8 (2 Η, m), 2. 4 〇 (3 Η, s), 2. 6 8 (4 Η, m), 2 · 9 6 (2 Η, t), printed by the Consumer Cooperatives of the Central Bureau of Standards of the Ministry of Economic Affairs (please read the precautions on the back before filling this page) 3 · 2 4 (4 Η, m ), 4 · 3 7 (2 Η, Q), 5 · 8 4 (2 Η, s), 7 · 1 6 (1 Η, d), 7. 5 2 (2 Η, d), 7 · 8 2 (1 Η, d), this paper size applies to Chinese National Standard (CNS) A4 (210X 297 mm) -90-printed by the Staff Consumer Cooperative of the Central Standards Bureau of the Ministry of Economic Affairs 524805 A7 B7 __ V. Description of the invention (88 ) 8 · 1 6 (1 Η, s), 8 · 1 8 (2 Η, d), 10.92 (lH, s). Example 5 2 1 Mono (2-aminobenzyl) -5— [2-ethoxy-5— (4-methylhexahydropyridine-1—1-sulfosulfanyl) phenyl] 3-n-propyl -1,6-dihydro-7H-pyrazolo [4,3-d] pyrimidin-7-one, Raney nickel catalyst (300 mg) was added to Example 4 9 In a stirred suspension of 40 m 1 of methanol), the mixture was hydrogenated at 3 45 kPa (50 Psi) and 50 ° C for 20 hours, then cooled and filtered. The filter was washed with methanol (50 m 1), and the methanol solution was combined and evaporated under reduced pressure. The obtained residue was purified by column chromatography using dichloromethane: methanol (95: 5) as an eluent on silica gel, and then crystallized from ethyl acetate to give the title compound (190 mg) as a white powder. Elemental analysis: 値: C, 5 8 · 9 8; Η, 6 · 2 0; N, 17 · 25. C28H35N704. Calculated 値 C, 59.45; H, 6.24; N, 17.33%. 5 (CDC 1 3): 1.0 (3H, t), 1. 6 4 (3 Η, t), 1 · 8 3 (2 Η, m), 2 · 2 7 (3 Η, s), 2 · 4 8 (4 Η, m),

本紙張尺度適用中國國家標準（CNS ) A4規格（210\ 297公楚一)~7q^\Z (請先閱讀背面之注意事項再填寫本頁)This paper size applies to China National Standard (CNS) A4 specifications (210 \ 297 Gongchu 1) ~ 7q ^ \ Z (Please read the precautions on the back before filling this page)

524805 經濟部中央標率局員工消費合作社印製 Α7 Β7 五、發明説明（89 ) 2 · 9 2 ( 2 Η，t )， 3 · 1 〇 ( 4 Η，m )， 4 · 3 9 ( 2 Η，Q )， 4 · 7 8 ( 2 Η，s )， 5 · 6 9 ( 2 Η，s )， 6 · 7 Ο ( 2 Η，m )， 7 · 1 2 ( 2 Η，m )， 7 · 5 8 ( 1 Η，d )， 7 · 8 2 ( 1 Η，d )， 8 · 8 Ο ( 1 Η，s )， 10.85(lH，s)。 實施例5 3 1一（2 —胺卡基）—5 — {5 —〔4 一（2 —經乙 基）六氫吡哄一 1 一基磺醯基〕一 2 —正丙氧苯基} 一 3 —正丙基一 1，6 -一氯—7H - π比哩並〔4，3 — d〕 赠π定一 7 -丽 由實施例5 0之標題化合物依實施例5 2之步驟製得 ’但係以乙酸乙酯：甲醇（9 5 : 5 )爲層析沖提液，而 以乙醇爲結晶步驟之溶劑，結果呈白色晶狀固體（5 4 % )° 5(CDCl3):l.〇l(3H，t)， 1 · 2 0 ( 3 Η，t )， 1 · 8 4 ( 2 Η，m )， (請先閱讀背面之注意事項再填寫本頁) -524805 Printed by the Consumer Cooperatives of the Central Standards Bureau of the Ministry of Economic Affairs Α7 Β7 V. Description of the invention (89) 2 · 9 2 (2 Η, t), 3 · 1 〇 (4 Η, m), 4 · 3 9 (2 Η , Q), 4 · 7 8 (2 Η, s), 5 · 6 9 (2 Η, s), 6 · 7 Ο (2 Η, m), 7 · 1 2 (2 Η, m), 7 · 5 8 (1 Η, d), 7 · 8 2 (1 Η, d), 8 · 8 Ο (1 Η, s), 10.85 (lH, s). Example 5 3 1 1- (2-aminocarbyl) -5— {5 — [4-((2-Ethyl) hexahydropyridine—1- 1-sulfosulfanyl]-2-n-propoxyphenyl}} A 3-n-propyl-1,6-chloro- 7H-π specific mile [4,3 — d] donated π- 7-Li was prepared from the title compound of Example 50 according to the procedure of Example 5 2 Obtained, but with ethyl acetate: methanol (95: 5) as the chromatographic eluent, and ethanol as the solvent of the crystallization step, the result was a white crystalline solid (54%) ° 5 (CDCl3): l .〇l (3H, t), 1 · 2 0 (3 Η, t), 1 · 8 4 (2 Η, m), (Please read the notes on the back before filling this page)-

、1T 本纸張尺度適用中國國家標準（CNS ) Α4規枱（210Χ297公t ) - 92 - 524805 A7 B7 五、發明説明（90 ) 2 · 0 5 ( 2 Η，m )， 2 · 3 〇（1 Η，s )， 2 · 5 7 ( 2 Η，t )， 2 · 6 〇（4 Η，m )， 2 · 9 2 ( 2 Η，t )， 3 · 1 Ο ( 4 Η，m )， 3 · 5 8 ( 2 Η，m )， 4 · 2 6 ( 2 Η，t )， 4 · 7 8 ( 2 Η，s )， 5 · 6 8 ( 2 Η，s )， 6 . 7 Ο ( 2 Η，m )， 7 · Ο 8 ( 1 Η，m )， 7 · 1 8 ( 1 Η，d )， 7 · 5 7 ( 1 Η，d )， 7 · 8 2 ( 1 Η，d )， 8 · 8 1 ( 1 Η，s )， 1 Ο · 9 8 ( 1 Η，s )。 LRMS:m/z 610(Μ+1)+。 經濟部中央標準局員工消費合作社印製 (請先閱讀背面之注意事項再填寫本頁) 實施例5 4 1— (4 —胺苄基）—5 —〔2 —乙氧一5 — (4 — 甲基六氣哦α井—1 一基磺醯基）—苯基〕一 3 —正丙基一 1，6 -二氫—7Η —吡唑並〔4，3 — d〕嘧啶—7 — 酮 本紙張尺度適用中國國家標準（CNS ) 規格（210X 297公釐）-93- 524805 A7 B7 五、發明説明（91 ) 由實施例5 1之標題化合物依實施例5 2之步驟製得 ，呈白色固體（88%)。 元素分析實測値：C，5 9 · 3 8 ; Η，6 · 2 8 ; N， 17.0〇°C28H35N7〇4S計算値 C，59.45;H，6.24;N，17.33%。 5(CDCl3):l.〇〇（3H，t)， 1 . 6 5 ( 3 Η，t )， 1 · 8 7 ( 2 Η，m )， 2 · 2 8 ( 3 Η，s )， 2 · 5 Ο ( 4 Η，m )， 2 · 9 2 ( 2 Η，t )， 3 · 1 Ο ( 4 Η，m )， 3 · 6 1 ( 2 Η，s )， 4 · 3 6 ( 2 Η，q )， 5 · 6 2 ( 2 Η，s )， 6 · 6 Ο ( 2 Η，d )， 7 · 1 3 ( 1 Η，d )， 7 · 2 6 ( 2 Η，d )， 經濟部中央標準局員工消費合作社印製 (請先閱讀背面之注意事項再填寫本頁) 7.82(lH，d)， 8 · 8 2 ( 1 Η，s )， 10.83(lH，s)° LRMS:m/z 566 (M+1)+。 實施例5 5 本纸張尺度適用中國國家標準（CNS ) A4規桔（210X 297公釐）-94 - 524805 A7 B7 - ' ~~ . ·~ — — 五、發明説明（92 ) 5 —〔2 —乙氧一5 —（4 一甲基六氫吡畊—1〜基 磺醯基）苯基〕一 1 一（2 一甲丨兀磺醯胺爷基）一 3 —正 丙基—1，6 —二氫一 7H - D比哩並〔4 ’ 3 — d〕喷η定 —7 —酮 將甲烷磺醯氯（31A1 ’ 〇 · 40mmo 1)加入 一以冰冷卻而含有實施例5 2標題化合物（置於3 ^ 1吼 啶中）的攪拌溶液裡，在室溫下攪拌此混合物2小時，然 後減壓蒸發。所得殘餘物以水（1 〇 m 1 )處理過後用二 氯甲烷（總量4 0 m 1 )對該懸浮液進行萃取。合倂的萃 取液經乾燥（N a 2 S 0 4 )後減壓蒸發而得到橙色油狀物 ，以層析法利用乙酸乙酯：甲醇：〇 · 8 8 0氨水（9 4 :5 : 1 )爲沖提液在矽膠上純化該油狀物而得到白色泡 沬狀的標題化合物（6 2 m g )。 元素分析實測値：C，5 4 · 0 3 ; Η，5 · 8 7 ; N ’ 14 . 7 0。C29H37N7〇6S2 計算値 (請先閱讀背面之注意事項再填寫本頁) 經濟部中央標準局員工消費合作社印製 ο 3HHHHHHH 113234272 • c κίν xc r\ rx /l\ rv r\ 4D6080609 5C6925913 > /V · c t112 2 CN3 oo 4 N 9 7 5 Η % 3 2 5、 1T This paper size applies Chinese National Standard (CNS) A4 gauge (210 × 297g t)-92-524805 A7 B7 5. Description of the invention (90) 2 · 0 5 (2 Η, m), 2 · 3 〇 ( 1 Η, s), 2 · 5 7 (2 Η, t), 2 · 6 〇 (4 Η, m), 2 · 9 2 (2 Η, t), 3 · 1 〇 (4 Η, m), 3 · 5 8 (2 Η, m), 4 · 2 6 (2 Η, t), 4 · 7 8 (2 Η, s), 5 · 6 8 (2 Η, s), 6. 7 Ο (2 Η, m), 7 · 〇 8 (1 Η, m), 7 · 1 8 (1 Η, d), 7 · 5 7 (1 Η, d), 7 · 8 2 (1 Η, d), 8 · 8 1 (1 Η, s), 1 〇 · 9 8 (1 Η, s). LRMS: m / z 610 (M + 1) +. Printed by the Consumer Cooperatives of the Central Standards Bureau of the Ministry of Economic Affairs (please read the precautions on the back before filling this page) Example 5 4 1— (4-aminobenzyl) —5 — [2 —Ethoxyl 5 — (4 — Methylhexyl-α-α-1 sulfosulfanyl) -phenyl] -3-n-propyl-1,6-dihydro-7H-pyrazolo [4,3-d] pyrimidin-7-one This paper size applies Chinese National Standard (CNS) specifications (210X 297 mm) -93- 524805 A7 B7 V. Description of the invention (91) Prepared from the title compound of Example 51 according to the procedure of Example 52, white Solid (88%). Elemental analysis: 値: C, 5 9 · 3 8; Η, 6 · 2 8; N, 17.0 ° C 28H35N704. Calculate 値 C, 59.45; H, 6.24; N, 17.33%. 5 (CDCl3): 1.0 (3H, t), 1.6 5 (3 Η, t), 1 · 8 7 (2 Η, m), 2 · 2 8 (3 Η, s), 2 · 5 〇 (4 Η, m), 2 · 9 2 (2 Η, t), 3 · 1 〇 (4 Η, m), 3 · 6 1 (2 Η, s), 4 · 3 6 (2 Η, q), 5 · 6 2 (2 Η, s), 6 · 6 Ο (2 Η, d), 7 · 1 3 (1 Η, d), 7 · 2 6 (2 Η, d), Central Ministry of Economic Affairs Printed by the Consumer Bureau of Standards Bureau (please read the precautions on the back before filling this page) 7.82 (lH, d), 8 · 8 2 (1 Η, s), 10.83 (lH, s) ° LRMS: m / z 566 (M + 1) +. Example 5 5 This paper size applies the Chinese National Standard (CNS) A4 orange (210X 297 mm) -94-524805 A7 B7-'~~. · ~ — — V. Description of the invention (92) 5 — [2 —Ethoxy-5 — (4-methylhexahydropyridine — 1 ~ sulfosulfanyl) phenyl] — 1 — (2 —methylsulfonamido) — 3 —n-propyl-1, 6-Dihydro-7H-D specific mile and [4 '3 — d] spray η--7-one Add methanesulfonyl chloride (31A1' 0. 40mmo 1) to one ice-cooled to contain Example 5 2 title In a stirred solution of the compound (in 3 ^ 1 aziridine), the mixture was stirred at room temperature for 2 hours, and then evaporated under reduced pressure. The resulting residue was treated with water (100 m 1), and the suspension was extracted with dichloromethane (a total of 40 m 1). The combined extract was dried (N a 2 S 0 4) and evaporated under reduced pressure to obtain an orange oil. Chromatography was performed using ethyl acetate: methanol: 0.88 aqueous ammonia (9 4: 5: 1 ) The oil was purified on silica gel for the eluent to give the title compound (62 mg) as a white foam. Elemental analysis: 値: C, 5 4 · 0 3; Η, 5 · 8 7; N ′ 14.7. C29H37N7〇6S2 Calculation 値 (Please read the notes on the back before filling out this page) Printed by the Consumer Cooperatives of the Central Bureau of Standards of the Ministry of Economic Affairs 3 3HHHHHHH 113234272 C t112 2 CN3 oo 4 N 9 7 5 Η% 3 2 5

NJy \)y \)y \ly \iy \)y \)/tms m tmQ Η 3 Γ\ 2 ο 本纸張尺度適用中國國家標準（CNS)A4規枱（21〇χ 297公漦）_95_ 524805 .A7 B7 五、發明説明（93) 5 · 7 9 ( 2 Η，s )， 7 · 1 8 ( 2 Η，m )， 7 · 3 6 ( 1 Η，m )， 7 · 6 Ο ( 1 Η，d )， 7 · 7 2 ( 1 Η，d )， 7 · 8 3 ( 1 Η，d )， 8 · 8 Ο ( 1 Η，s )， 9 · 6 8 ( 1 Η，s )， 10.95(lH，s)。 L R Μ S ： m / ζ 644 (Μ+1)+〇 實施例5 6 5 — {5 —〔4 一（2 —羥乙基）六氫吡哄一 1—基 磺醯基〕一 2 -正丙氧苯基} 一1 一（2 —甲烷磺醯胺苄 基）一 3 -正丙基—1，6 —二氫ί 一 7Η —卩比哩並〔4， 3 - d〕嘧啶—7 —酮 把氟化四正丁基銨於四氫呋喃中所形成的1 Μ溶液（ 經濟部中央標準局員工消費合作社印製 (請先閱讀背面之注意事項再填寫本頁) 0 · 27ml ，0 · 27mmo 1)加入製備例98標題 化合物（145mg，〇 · 18mmo 1)與四氫呋喃（ 3 m 1 )的攪拌溶液裡。於室溫下經2 0小時之後加水（ 5ml)，再將產生的混合物用乙酸乙酯（總量2 0 m 1 )萃取’合倂的萃取液經乾燥（N a 2 S〇4 )後減壓蒸發 而得到黃色油狀物。以管柱層析法利用乙酸乙酯：甲醇： 0 · 8 8 0氨水（9 4 : 5 : 1 )爲沖提液在矽膠上純化 本纸張尺度適用中國國家標準（CNS ) A4規枱（210X29*7公釐）-96 - 經濟部中央標準局員工消費合作社印製 524805 五、發明説明（94 ) 該黃色油狀物，接著由乙酸乙酯再結晶而得到呈白色固體 之標題化合物（8 3mg)。 元素分析實測値：C，5 3 · 8 9 ; Η，6 · 0〇；N， 14 · 09。C31H4!N7〇7S2 計算値 C，54.13;H，6.〇1;N，14.25%。 5(CDCl3):l.〇2(3H，t)， 1 · 2 0 ( 3 Η，t )， 1 · 9 〇（2 Η，m )， 2 · 0 6 ( 2 Η，m )， 2 · 2 8 ( 1 Η，s )， 2 · 5 6 ( 2 Η，m )， 2 · 6 0 ( 4 Η，m )， 2 · 9 6 ( 2 Η，t )， 3 · 1 〇（7 Η，m )， 3 · 5 7 ( 2 Η，m )， 4 · 2 8 ( 2 Η，t )， 5 · 7 9 ( 2 Η，s )， 7 · 1 8 ( 2 Η，m )， 7 · 3 6 ( 1 Η，m )， 7 · 6 0 ( 1 Η，d )， 7 · 7 〇（1 Η，d )， 7.84(lH，d)， 8 · 8 2 ( 1 H，s )， 9 . 6 8 ( 1 H ，s )， 本纸張尺度適用中國國家標準（〇奶）/\4規梏（210/297公釐）-97 - (請先閲讀背面之注意事項再填寫本頁) -. -一口 524805 kl B7 五、發明説明（95 ) l〇.99(lH，s)。 實施例5 7 5 —〔2 —乙氧一 5— (4 —甲基六氫吡哄一1 一基 礦薩基）苯基〕_1 一（4 一甲垸礦酸胺节基）一 3 -正 丙基一 1，6 —二氫—7H_吡唑並〔4，3 — d〕嘧啶 -7 —酮 由實施例5 4之標題化合物依實施例5 5之步驟製得 ，呈白色固體（64%)。 元素分析實測値：C，5 1 · 1〇；Η，6 · 0 1 ; N， 13 · 8 5° C29H37N7O6S2 ； 2Η2〇計算値 C ， 51.23 ;Η，6·08;Ν，14.42%。 5(CDCl3):l.〇〇（3H，t)， 1 · 6 2 ( 3 Η，t )， 1 · 8 6 ( 2 Η，m )， 2 · 2 8 ( 3 Η，s )， 2 · 5 〇（4 Η，m )， 2 · 9 4 ( 5 Η，m )， 經濟部中央標準局員工消費合作社印製 (請先閲讀背面之注意事項再填寫本頁) 3 · 1 2 ( 4 Η，m )， 4 · 3 6 ( 2 Η，q )， 5 · 6 2 ( 2 Η，s )， 7 · 1 5 ( 4 Η，m )， 7 · 3 8 ( 2 Η，d )， 7 · 8 2 ( 1 Η ，d )， 本纸張尺度適用中國國家標準（CNS ) A4規枱（210X297公釐）-98 - 524805 A7 B7 五、發明説明（96 ) 8 · 7 5 ( 1 Η，S )， l〇.94(lH，s)。 LRMS:m/z 644(M+1) +。 實施例5 8 5 —〔2 —乙氧一 5— (4 —甲基六氫吡哄一1—基 磺醯基）苯基〕一 3 -正丙基一 1 一（4 一胺磺醯苄基） —1，6 —二氫一 7 Η -吡唑並〔4，3 — d〕嘧啶—7 一酮 由製備例9 9之標題化合物及1 -甲基六氫吡畊依實 施例1之步驟製得，呈細白色固體（3 9 % )。 元素分析實測値：C，5 1 · 7 2 ; Η，5 · 4 2 ; N， 1 4 . 85 。C28H35N7〇6S2; Η2〇計算値 C，51.92;H，5.76;N，15.14%。 5(CDCl3):1.00(3H，t) ， 1 · 6 4 ( 3 Η，t )， 2 · 2 8 ( 3 Η，m )， 2 . 5 0 ( 4 Η，m )， 經濟部中央標準局員工消費合作社印製 (請先閱讀背面之注意事項再填寫本頁) 2 · 9 5 ( 2 Η，t )， 3 · 1 0 ( 4 Η，m )， 4 · 3 7 ( 2 Η，Q )， 4 · 7 5 ( 2 Η，s )， 5 · 8 0 ( 2 Η，s )， 7 · 1 6 ( 2 Η ，d )， 本紙張尺度適用中國國家標準（CNS ) A4規枱（210X 297公f ) - 99 - 524805 A7 五、發明説明（97 ) 7 · 5 2 ( 2 Η，d )， 7 · 8 4 ( 3 Η，m )， 8 · 8 4 ( 1 Η ， s )， 10.9〇（lH，s)。 經濟部中央標準局員工消費合作社印製 實施例5 9 5 — [ 2 — 乙 氧 — 5 — 磺 醯 基 ) 苯 基 ] — 3 — 甲 基 — 2 ， 6 — 二 氫 — 7 H — 吡 — 酮 由 製 備 例 4 2 之 標 題 化 施 例 1 之 步 驟 製 得 呈 黃 褐 5 ( D Μ S 〇 d 6 ) ； 1 • 3 2 • 2 〇 ( 3 Η y s ) ? 2 • 5 〇 ( 7 Η ， m ) ? 3 • 〇 6 ( 4 Η 5 m ) j 4 • 1 4 ( 2 Η Q ) 5 5 • 6 6 ( 2 Η ， s ) ? 7 • 〇 6 ( 1 Η d ) ， 7 • 2 〇 ( 1 Η 5 d ) 7 • 3 2 ( 1 Η 1 m ) 5 7 • 6 4 ( 1 Η ? d ) 7 • 7 8 ( 1 Η > m ) ， 7 9 〇 ( 1 Η 5 s ) ， (4 —甲基六氫吡畊一1 一基 —2 —(哦11定一2 —基）甲基 唑並〔4，3 - d〕嘧啶—7 合物及1 -甲基六氫吡畊依實 色固體（5 7 % )。 0 ( 3 Η，t )， (請先閱讀背面之注意事項再填寫本頁) 本紙張尺度適用中國國家標準（CNS ) A4規桔（21〇'〆297公t ) - 100 - 524805 A 7 B7 五、發明説明（98 ) 8 · 5 0 ( 1 Η，d )， 11.58(lH，s)。 L R M S ： m / z 542 (M+18)+。 實施例6 0 5— {2 —乙氧—5 —〔4 — (2 —羥乙基）六氫吡 哄一 1 一基磺醯基〕苯基〕一 3 —甲基一 2 —（吡啶一 2 一基）甲基一 2，6 —二氫一7H —吡唑並〔4，3 — d 〕嘧啶一 7 -酮 由製備例4 2之標題化合物及1 一（ 2 -羥乙基）六 氫吡哄依實施例1之步驟製得，呈黃褐色泡沬狀（4 7 % (請先閱讀背面之注意事項再填寫本頁) 經濟部中央標準局員工消費合作社印製 3 Η ΗΗΗΗΗΗΗΗΗΗ 132442221111 ο /IV /(V /(V /ν /IV /(V /IV /(V Γν /(V /IV D05648478082 C55725259116 '^—^ ·····_····· 522233456777 Η 3 /(\ 2 5 stmmmqsddmm \)/ \)y 本紙張尺度適用中國國家標準（CNS ) Α4規桔（210Χ 297公釐）-101 - 524805 Α7 Β7 經濟部中央標準局員工消費合作社印製 五、發明説明（99) 7 · 8 8 ( 1 Η，d )， 8 · 5 〇（1 Η，d )， 8 . 7 2 ( 1 Η，s )。 實施例6 1 5 —〔2 —甲氧一5 — (4 —甲基六氫吡畊一1 一基 磺醯基）苯基〕一 3 -正丙基一 2 -（吡啶—2 -基）甲 基一 2，6 —二氫—7H -吡唑並〔4，3 — d〕嘧啶一 7 —酮 由製備例4 3之標題化合物及1 -甲基六氫吡畊依實 施例1之步驟製得，呈無色油狀物（1 9 % )。 元素分析實測値：C，5 6 · 4 4 ; Η，5 · 7 6 ; N， 17 · 86 。C26H31N7〇4S ; H2〇計算値 C，56.16;H，5.94;N，17.64%。 5(CDCl3):0.94(3H，t) ， 1 · 7 6 ( 2 Η，m )， 2 · 2 8 ( 3 Η，s )， 2 · 5 Ο ( 4 Η，m )， 2 . 9 8 ( 2 Η > t )， 3 · 1 〇（4 Η，m )， 4 · 1 2 ( 3 Η，s )， 5 · 6 8 ( 2 Η，s )， 了 · Ο 8 ( 1 Η，d )， 7 · 1 8 ( 2 Η，m )， (請先閱讀背面之注意事項再填寫本頁)NJy \) y \) y \ ly \ iy \) y \) / tms m tmQ Η 3 Γ \ 2 ο This paper size applies to China National Standard (CNS) A4 gauge (21〇χ 297 公 漦) _95_ 524805 .A7 B7 V. Description of the invention (93) 5 · 7 9 (2 Η, s), 7 · 1 8 (2 Η, m), 7 · 3 6 (1 Η, m), 7 · 6 Ο (1 Η , D), 7 · 7 2 (1 Η, d), 7 · 8 3 (1 Η, d), 8 · 8 Ο (1 Η, s), 9 · 6 8 (1 Η, s), 10.95 ( lH, s). LR M S: m / ζ 644 (Μ + 1) + 〇 Example 5 6 5 — {5 — [4-mono (2-hydroxyethyl) hexahydropyridine—1-sulfofluorenyl] —2-n Propoxyphenyl}-1-1-(2-methanesulfonyl benzyl)-3 -n-propyl-1, 6-dihydrol-7Η-hydrazone [4, 3-d] pyrimidine-7 — Ketone 1 M solution of tetra-n-butylammonium fluoride in tetrahydrofuran (printed by the Consumer Cooperative of the Central Standards Bureau of the Ministry of Economic Affairs (please read the precautions on the back before filling this page) 0 · 27ml, 0 · 27mmo 1 ) Was added to a stirred solution of the title compound of Preparation 98 (145 mg, 0.18 mmo 1) and tetrahydrofuran (3 m 1). After 20 hours at room temperature, water (5 ml) was added, and the resulting mixture was extracted with ethyl acetate (total 20 m 1). The combined extract was dried (N a 2 S04) and then reduced. Evaporate under pressure to give a yellow oil. Purification by column chromatography using ethyl acetate: methanol: 0 · 8 8 0 ammonia (9 4: 5: 1) as the eluent on silica gel. This paper is sized to Chinese National Standard (CNS) A4 gauge ( 210X29 * 7mm) -96-Printed by the Consumer Cooperatives of the Central Standards Bureau of the Ministry of Economic Affairs 524805 5. Invention Description (94) The yellow oil was recrystallized from ethyl acetate to give the title compound (8 3mg). Elemental analysis: 値: C, 5 3 · 8 9; Η, 6 · 0〇; N, 14 · 09. C31H4! N7〇7S2 Calculated 値 C, 54.13; H, 6.01; N, 14.25%. 5 (CDCl3): 1.02 (3H, t), 1 · 2 0 (3 Η, t), 1 · 9 〇 (2 Η, m), 2 · 0 6 (2 Η, m), 2 · 2 8 (1 Η, s), 2 · 5 6 (2 Η, m), 2 · 6 0 (4 Η, m), 2 · 9 6 (2 Η, t), 3 · 1 〇 (7 Η, m), 3 · 5 7 (2 Η, m), 4 · 2 8 (2 Η, t), 5 · 7 9 (2 Η, s), 7 · 1 8 (2 Η, m), 7 · 3 6 (1 Η, m), 7 · 6 0 (1 Η, d), 7 · 7 〇 (1 Η, d), 7.84 (lH, d), 8 · 8 2 (1 H, s), 9. 6 8 (1 H, s), this paper size applies Chinese national standard (〇 奶) / \ 44 (210/297 mm) -97-(Please read the precautions on the back before filling this page)- -口 524805 kl B7 V. Description of the invention (95) l9.99 (lH, s). Example 5 7 5 — [2 —Ethoxy-5— (4-methylhexahydropyridine—1 1-based sapyl) phenyl] 1— (4—methylformite amine benzyl) —3- N-propyl-1,6-dihydro-7H_pyrazolo [4,3-d] pyrimidin-7-one was prepared from the title compound of Example 5 4 according to the procedure of Example 55, as a white solid ( 64%). Elementary analysis: 値: C, 5 1 · 10; Η, 6 · 0 1; N, 13 · 8 5 ° C29H37N7O6S2; 2 Η 20 Calculate 値 C, 51.23; Η, 6.08; N, 14.42%. 5 (CDCl3): 1.0 (3H, t), 1.62 (3 Η, t), 1 · 8 6 (2 Η, m), 2 · 2 8 (3 Η, s), 2 · 5 〇 (4 Η, m), 2 · 9 4 (5 Η, m), printed by the Consumer Cooperatives of the Central Standards Bureau of the Ministry of Economic Affairs (please read the precautions on the back before filling out this page) 3 · 1 2 (4 Η , M), 4 · 3 6 (2 Η, q), 5 · 6 2 (2 Η, s), 7 · 1 5 (4 Η, m), 7 · 3 8 (2 Η, d), 7 · 8 2 (1 Η, d), this paper size applies to Chinese National Standard (CNS) A4 gauge (210X297 mm) -98-524805 A7 B7 V. Description of the invention (96) 8 · 7 5 (1 Η, S ), 10.94 (lH, s). LRMS: m / z 644 (M + 1) +. Example 5 8 5 — [2-Ethoxy-5— (4-methylhexahydropyridine-1,1-sulfosulfanyl) phenyl] 3-3-n-propyl-1 1- (4-aminesulfamobenzyl Group) —1,6 —dihydro-7 pyrene-pyrazolo [4,3 — d] pyrimidin-7 monoone from the title compound of Preparation Example 9 9 and 1-methylhexahydropyridine according to Example 1 Prepared as a fine white solid (39%). Elemental analysis: 値: C, 5 1 · 7 2; Η, 5 · 4 2; N, 1 4. 8.5. C28H35N7〇6S2; Η20 calculations; C, 51.92; H, 5.76; N, 15.14%. 5 (CDCl3): 1.00 (3H, t), 1 · 6 4 (3 Η, t), 2 · 2 8 (3 Η, m), 2. 5 0 (4 Η, m), Central Bureau of Standards, Ministry of Economic Affairs Printed by the employee consumer cooperative (please read the notes on the back before filling out this page) 2 · 9 5 (2 Η, t), 3 · 1 0 (4 Η, m), 4 · 3 7 (2 Η, Q) , 4 · 7 5 (2 Η, s), 5 · 8 0 (2 Η, s), 7 · 1 6 (2 Η, d), this paper size applies Chinese National Standard (CNS) A4 gauge (210X 297) F)-99-524805 A7 V. Description of the invention (97) 7 · 5 2 (2 Η, d), 7 · 8 4 (3 Η, m), 8 · 8 4 (1 Η, s), 10.9〇 (LH, s). Printed by the Consumer Cooperative of the Central Bureau of Standards of the Ministry of Economic Affairs Example 5 9 5 — [2 —Ethoxy — 5 —sulfonyl) phenyl] — 3 —Methyl — 2, 6 —Dihydro — 7 H — Pyridone Yellow Brown 5 (D M S 〇d 6) was prepared by the steps of the titled Example 1 of Preparation Example 4 2; 1 • 3 2 • 2 〇 (3 Η ys)? 2 • 5 〇 (7 ，, m )? 3 • 〇6 (4 Η 5 m) j 4 • 1 4 (2 Η Q) 5 5 • 6 6 (2 Η, s)? 7 • 〇6 (1 Η d), 7 • 2 〇 (1 Η 5 d) 7 • 3 2 (1 Η 1 m) 5 7 • 6 4 (1 Η? D) 7 • 7 8 (1 Η > m), 7 9 〇 (1 Η 5 s), (4 — Methylhexahydropyridine-1 1-yl-2 — (Oh, 11Adi-2-yl) methylazolo [4,3-d] pyrimidine-7 and 1-methylhexahydropyridine Solid (57%). 0 (3 Η, t), (Please read the notes on the back before filling in this page) This paper size applies the Chinese National Standard (CNS) A4 standard orange (21〇'297297 t) -100-524805 A 7 B7 V. Description of the invention (98) 8 · 5 0 (1 Η, d), 11.58 (lH, s). LRMS: m / z 542 (M + 18) +. Example 6 0 5 — {2 —ethoxy — 5 — [4 — (2-hydroxy Ethyl) hexahydropyridine-1 1-sulfofluorenyl] phenyl]-3-methyl-1 2- (pyridine-2 2-yl) methyl-2,6-dihydro-7H-pyrazolo [4 , 3-d] Pyrimidine-7-one was prepared from the title compound of Preparation 4 and 1- (2-hydroxyethyl) hexahydropyridine according to the procedure of Example 1, and was yellow-brown in the shape of a foam (4 7 % (Please read the notes on the back before filling this page) Printed by the Consumer Cooperatives of the Central Bureau of Standards of the Ministry of Economic Affairs 3 Η ΗΗΗΗΗΗΗΗΗΗ 132442221111 ο / IV / (V / (V / ν / IV / (V / IV / (V Γν / (V / IV D05648478082 C55725259116 '^ — ^ ···· __ ···· 522233456777 Η 3 / (\ 2 5 stmmmqsddmm \) / \) y This paper standard applies to the Chinese National Standard (CNS) Α4 standard orange (210 × 297 mm) -101-524805 Α7 Β7 Printed by the Consumers' Cooperative of the Central Standards Bureau of the Ministry of Economic Affairs 5. Description of the invention (99) 7 · 8 8 (1 Η, d), 8 · 5 〇 (1 Η, d) , 8. 7 2 (1 Η, s). Example 6 1 5-[2-Methoxy-5-(4-methylhexahydropyridine-1 1-ylsulfonyl) phenyl] -3-n-propyl-2-(pyridine-2-yl) Methyl-2,6-dihydro-7H-pyrazolo [4,3-d] pyrimidin-7-one was prepared from the title compound of Preparation 4 3 and 1-methylhexahydropyridine according to the procedure of Example 1 Obtained as a colorless oil (19%). Elemental analysis: 値: C, 5 6 · 4 4; Η, 5 · 7 6; N, 17 · 86. C26H31N7004S; H20 calculated 値 C, 56.16; H, 5.94; N, 17.64%. 5 (CDCl3): 0.94 (3H, t), 1 · 7 6 (2 Η, m), 2 · 2 8 (3 Η, s), 2 · 5 Ο (4 Η, m), 2. 9 8 ( 2 Η > t), 3 · 1 〇 (4 Η, m), 4 · 1 2 (3 Η, s), 5 · 6 8 (2 Η, s), · 8 (1 Η, d) , 7 · 1 8 (2 Η, m), (Please read the notes on the back before filling this page)

IP 、τIP, τ

AT 本纸張尺度適用中國國家標準（CNS ) A4規格（21〇Χ297公釐）· 102 - 524805 A 7 B7 五、發明説明（彳00) 7 · 6 3 ( 1 Η，m )， 7 · 8 6 ( 1 Η，d )， 8 · 5 8 ( 1 Η，d )， 8 · 7 8 ( 1 Η，s )， l〇.52(lH，s)。 L R M S ： m / z 538 (M+1)+。 實施例6 2 3 —乙基一 5 —〔5 -（六氮1:1比啡一 1 一基礦酸基） 一 2 —正丙氧苯基〕—2 —（吼D定—2 —基）甲基一 2， 6 —二氫一 7H —吡唑並〔4，3 — d〕嘧啶一 7 -酮 由製備例1 8之標題化合物及六氫吡啡依實施例1之 步驟製得，呈白色固體（33%)。 元素分析實測値·· C，5 7 · 4 0 ; Η，5 · 8 1 ; N， 17. 91 。C26H31N7〇4S ; 0 . 5〇H2〇計算値 (請先閱讀背面之注意事項再填寫本頁) 經濟部中央標準局員工消費合作社印製 3 3ΗΗΗΗΗΗΗ IX lx oo .A一 CO 00 OO H • c /IV /l\ /l\ /IV /l\ /(V /IV 7D0120268 5C3090260 ， /#l\······ C51223457 N ο 9 5 Η % 4 9 7 mmmt s d \)y \ \)/ Η 3 /ι\ 4 本紙張尺度適用中國國家標準（CNS ) A4規梏（210X 297公釐）-103 - 524805 A7 B7 五、發明説明（1〇1) 7 · 1 4 ( 1 Η，d )， 7 · 2 4 ( 1 Η，m )， 7 · 6 1 ( 1 Η，m )， 7 · 8 2 ( 1 Η，d )， 8 · 5 4 ( 1 Η，s )， 8 · 7 8 ( 1 Η，s )， 10.6〇（lH，s) 〇 L R M S ： m / z 538 (M+1)+。 實施例6 3 5 -〔5 -（六氫吡畊一 1 一基磺醯基）一 2 —正丙 氧苯基〕一 3 —正丙基—2 —（吡啶一 2 —基）甲基一 2 ，6 -二氫—7H —卩比嗤並〔4，3 — d〕嚼D定—7 —酮 三氟乙酸酯 經濟部中央標準局員工消費合作社印製 將三氟乙酸（4m 1 )加入一攪拌中由製備例4 4標 題化合物（388mg，〇 · 6mmo 1)於二氯甲烷（ 4 m 1 )所形成的溶液裡，於室溫下攪拌此混合物1 8小 時，然後減壓蒸發。殘餘物以管柱層柱法利用二氯甲烷： 甲醇：0 · 8 8 0氨水（9 7 : 3 : 1 )爲沖提液於矽膠 上進行純化而得到呈固體之標題化合物（6 5 % )。 元素分析實測値：C，51 · 93 ;H，5 · 14 ;N， 14 · 42 。C27H33N7〇4S ; CF3C〇2H 計算値 〇，52·32;Η，5·14;Ν，14·73%。 (5 ( D M S 0 d 6 ) :0.86(3H，t)， 本紙張尺度適用中國國家標準（CNS ) A4規桔（210X297公釐） 經浓部中央標準局員工消費合作社印製 524805 A7 B7 五、發明説明（1〇2) 1 · 1 4 ( 3 Η，t )， 1 · 6 5 ( 2 Η，m )， 1 · 7 4 ( 2 Η，m )， 2 · 9 4 ( 2 Η，t )， 3 · 1 2 ( 8 Η，m )， 4 . 1 4 ( 2 Η，t )， 5 · 6 8 ( 2 Η，s )， 7 · 2 1 ( 1 Η，d )， 7 · 3 4 ( 1 Η，m )， 7 · 4 1 ( 1 Η，d )， 7 · 8 〇（2 Η，m )， 7 · 9 2 ( 1 Η，s )， 8 · 1 2 ( 1 Η，s )， 8 · 5 1 ( 1 Η，d )， 11.74(lH，s)。 LRMS:m/z 573 (M+18)+。 實施例6 4 5 — {5 —〔4一（2 —甲氧乙基）六氫吡哄一1 — 基擴酶基〕2 -正丙氧苯基〕一 3 -正丙基—2 -（吼π定 —2 —基）甲基—2，6 —二氫一7H —吡唑並〔4，3 —d〕嘧啶一 7 -酮 由製備例2 0之標題化合物及1 一（ 2 —甲氧乙基） 六氫吡畊依實施例1之步驟製得，呈乳泡沬狀（5 8 % ) (讀先閲讀背面之注意事項再填寫本頁)AT This paper size applies to China National Standard (CNS) A4 specification (21〇 × 297 mm) · 102-524805 A 7 B7 V. Description of the invention (彳 00) 7 · 6 3 (1 Η, m), 7 · 8 6 (1 Η, d), 8 · 5 8 (1 Η, d), 8 · 7 8 (1 Η, s), 10.52 (1H, s). L R M S: m / z 538 (M + 1) +. Example 6 2 3 —Ethyl-5 — [5-(hexazine 1: 1 bisphrene-1 1 base mineral acid group) — 2 —n-propoxyphenyl] -2 — ) Methyl-2,6-dihydro-7H-pyrazolo [4,3-d] pyrimidin-7-one was prepared from the title compound of Preparation 18 and hexahydropyridine according to the procedure of Example 1, White solid (33%). Elemental analysis measured 値 ·· C, 5 7 · 4 0; Η, 5 · 8 1; N, 17. 91. C26H31N7〇4S; 0.50H2〇 calculation (please read the notes on the back before filling this page) Printed by the Consumer Cooperatives of the Central Standards Bureau of the Ministry of Economic Affairs 3 3ΗΗΗΗΗΗΗ IX lx oo .A-CO 00 OO H • c / IV / l \ / l \ / IV / l \ / (V / IV 7D0120268 5C3090260 ， / # l \ ····· C51223457 N ο 9 5 Η% 4 9 7 mmmt sd \) y \ \) / Η 3 / ι \ 4 This paper size applies the Chinese National Standard (CNS) A4 Regulation (210X 297 mm) -103-524805 A7 B7 V. Description of the Invention (101) 7 · 1 4 (1 Η, d), 7 · 2 4 (1 Η, m), 7 · 6 1 (1 Η, m), 7 · 8 2 (1 Η, d), 8 · 5 4 (1 Η, s), 8 · 7 8 (1 H, s), 10.6 (lH, s), LRMS: m / z 538 (M + 1) +. Example 6 3 5-[5-Hydroxypyridine-1 1-sulfosulfanyl] -2-n-propoxyphenyl] -3-n-propyl-2-(pyridine-2-yl) methyl-1 2,6 -dihydro-7H-pyridine [4,3 — d] chelate D-7-7-ketotrifluoroacetate Printed with trifluoroacetic acid (4m 1) A solution of the title compound of Preparation 4 4 (388 mg, 0.6 mmo 1) in dichloromethane (4 ml) was added to a stirring solution, and the mixture was stirred at room temperature for 18 hours, and then evaporated under reduced pressure. The residue was purified by column chromatography using dichloromethane: methanol: 0 · 8 8 0 ammonia (97: 3: 1) as the eluent and purified on silica gel to give the title compound as a solid (65%) . Elemental analysis of plutonium: C, 51 · 93; H, 5 · 14; N, 14 · 42. C27H33N7〇4S; CF3C〇2H calculated 値 〇, 52 · 32; Η, 5.14; N, 14.73%. (5 (DMS 0 d 6): 0.86 (3H, t), this paper size is applicable to Chinese National Standard (CNS) A4 regulations (210X297 mm). Printed by the Consumers' Cooperative of the Central Standards Bureau of the Ministry of Concentration. 524805 A7 B7.) Description of the invention (1〇2) 1 · 1 4 (3 Η, t), 1 · 6 5 (2 Η, m), 1 · 7 4 (2 Η, m), 2 · 9 4 (2 Η, t) , 3 · 1 2 (8 Η, m), 4. 1 4 (2 Η, t), 5 · 6 8 (2 Η, s), 7 · 2 1 (1 Η, d), 7 · 3 4 ( 1 Η, m), 7 · 4 1 (1 Η, d), 7 · 8 〇 (2 Η, m), 7 · 9 2 (1 Η, s), 8 · 1 2 (1 Η, s), 8 · 5 1 (1 Η, d), 11.74 (lH, s). LRMS: m / z 573 (M + 18) +. Example 6 4 5 — {5 — [4 一 (2-methoxyethyl) ) Hexahydropyridine 1-yl diammonyl] 2 -n-propoxyphenyl]-3-n-propyl-2-(n-pyridin-2-yl) methyl-2,6-dihydro-7H —Pyrazolo [4,3-d] pyrimidin-7-one was prepared from the title compound of Preparation Example 20 and 1- (2-methoxyethyl) hexahydropyridine according to the procedure of Example 1, and was milky. Bubble-like (5 8%) (Read the notes on the back first Then fill out this page)

本紙張尺度適用中國國家標準（CNS ) A4規桔（210X 297公楚）-1〇5 - 524805 A7 B7 五、發明説明（103) 8 Η H o 5 3 .，， c 9 c 。 4 値 8 · 測 ο 8 實 · 5 析 6 ， 分 1C 素，値 元 Ν 算 〇 5 2 2 Η 9 ; 5 . 5 3 5 Λ‘ . 1—I• 〇 ，6 ; N> s H 5 o 計 〇 % 經濟部中央標準局員工消費合作社印製 XHX THX THX Tu XHX Ji Tu J1 THX Ji THX T2 T2 Ji ΤΊ- THX —L 3τγτγτγτγτγτγτγτγτγτγτηχτγτγτγτγρτγ ^_ 132262432221111111c o /IV rv /(V /IV /{V /(V /IV /' /IV /IV /lx /V /l\ /(\ rv /(V /l\ nu D964982023965223876 C17 0 59134260126857 . /^*······*·········(丨u 5112223334577777881 Η 3 6 9 〇 (請先閱讀背面之注意事項再填寫本頁) t t sddmmdds \)/ xlyThis paper size applies to Chinese National Standard (CNS) A4 Orange (210X 297 Gongchu)-105-524805 A7 B7 V. Description of the invention (103) 8 Η H o 5 3., C 9 c. 4 値 8 · Measure ο 8 Real · 5 Analysis 6, divided into 1C element, the unit N is calculated as 〇5 2 2 Η 9; 5. 5 3 5 Λ '. 1—I • 〇, 6; N > s H 5 o Calculated by 0% Printed by the Consumer Cooperatives of the Central Standards Bureau of the Ministry of Economic Affairs XHX THX THX Tu XHX Ji Tu J1 THX Ji THX T2 T2 Ji ΤΊ- THX —L 3τγτγτγτγτγτγτγτγτγτγτγτηχτγτγτγτγτγρτγ ^ _ 132262432 221111111 (/ / IV V / IV / '/ IV / IV / lx / V / l \ / (\ rv / (V / l \ nu D964982023965223876 C17 0 59134260126857. / ^ * ... · (丨 u 5112223334577777881 Η 3 6 9 〇 (Please read the precautions on the back before filling in this page) tt sddmmdds \) / xly

H s 本紙張尺度適用中國國家標準（CNS ) A4規格（210X297公釐）-1 〇6 - 524805 A7 ______B7 五、發明説明（104) LRMS :m/z 610 (M+l)+。 實施例6 5 5 —〔5 —（4 一胺羰基甲基六氫吡畊一 1 一基磺醯 基）2 —正丙氧苯基〕一 3 -正丙基—2 -（吡啶一 2 — 基）甲基一2，6 —二氫一7H — d比口坐並〔4，3 — d〕 峰啶〜7 —酮 由製備例2 0之標題化合物及1 -胺羰基甲基六氫吡 ( Indian J. Chem., 1 984, 650 )依實施例 1 之步驟 _ ί# ’呈淺黃色泡沬狀（1 6 % )。 5 ( c D C 1 3 ) :0.95(3H，t)， anti— ml —.^—>1 Mmwam —-^ϋ nm «—>1 ml m (請先閲讀背面之注意事項再填寫本頁) 經濟部中央標準局員工消費合作衽印製 1122333456777H s This paper size is applicable to China National Standard (CNS) A4 specification (210X297mm) -1 〇6-524805 A7 ______B7 V. Description of the invention (104) LRMS: m / z 610 (M + l) +. Example 6 5 5-[5-(4-monoaminocarbonylmethylhexahydropyridine-1 1-sulfofluorenyl) 2-n-propoxyphenyl]-3 -n-propyl-2-(pyridine-2- (Methyl) methyl-2,6-dihydro-7H-d, and [4,3-d] peak pyridine ~ 7-one from the title compound of Preparation Example 2 and 1-aminocarbonylmethylhexahydropyridine (Indian J. Chem., 1 984, 650) According to the procedure of Example 1, it was light yellow foam (16%). 5 (c DC 1 3): 0.95 (3H, t), anti- ml —. ^ — ≫ 1 Mmwam —- ^ ϋ nm «— > 1 ml m (Please read the precautions on the back before filling this page ) Printed by the Consumer Standards Cooperative of the Central Bureau of Standards of the Ministry of Economic Affairs 1122333456777

Ji XI J1 Ji J1 Ji J1 THX Ji J1 THX THX -Jl ΤΓ- ΤΓ- THX ΤΓ- ΤΓ- ΤΓ- THX xhx t ΤΓ- ΤΓ- ΤΓ p 3224224222111 /(\ r\ /l\ /l\ /l\ rv r\ r\ /l\ /l\ /—^' /(\ /(\ 7354022896083 1706001266112 N)y N)/ \)/ \)/ \)ytmmm t smt ssddmJi XI J1 Ji J1 Ji J1 THX Ji J1 THX THX -Jl ΤΓ- ΤΓ- THX ΤΓ- ΤΓ- ΤΓ- THX xhx t ΤΓ- ΤΓ- ΤΓ p 3224224222111 / (\ r \ / l \ / l \ / l \ rv r \ r \ / l \ / l \ / — ^ '/ (\ / (\ 7354022896083 1706001266112 N) y N) / \) / \) / \) ytmmm t smt ssddm

、1T 本紙張尺度適用中國國家標準（CNS ) Α4規格（210X297公釐）_ 1〇7 - 524805 B7_ 五、發明説明（105) 7 · 6 3 ( 1 Η，m )， 7 · 8 6 ( 1 Η，d )， 8 · 5 9 ( 1 Η，d )， 8 · 8 0 ( 1 Η，s )， 10.62(lH，s)。 L R M S ： m / z 6〇9(M+1)+。 實施例6 6 2 —（3 —甲氧吡啶一2 —基）甲基一5 —〔5 —( 4 一甲基六氫吡畊一 1 一基磺醯基）2 -正丙氧苯基〕一 3 —正丙基—2，6 — —*氫/— 7H —吼嗤並〔4，3 — d 〕嚼D定一 7 -酮 由製備例4 8之標題化合物及1 -甲基六氫吡畊依實 施例1之步驟製得，呈白色固體（8 2 % )。 元素分析實測値：C，5 7 · 6 0 ; Η，6 · 2 3 ; N， 15 · 92 。C29H37N7〇5S ;〇· 50H2〇計算値 C，57. 60;Η，6·33;Ν，16.21%。 經濟部中央標準局員工消費合作社印製 (請先閱讀背面之注意事項再填寫本頁) 5 ( C D C 1 3 ) :0,94(3H，t)， 1 ·〇 9 ( 3 H，t )， 1 · 7 8 ( 2 H，m )， 1 · 9 8 ( 2 H，m )， 2 · 2 3 ( 3 H，s )， 2 · 4 4 ( 4 H，m )， 2 · 9 6 ( 2 H ， t )， 本纸張尺度適用中國國家標準（CNS ) A4規格（210X29?公釐）-1〇8 524805 A7 B7 五、發明説明（1〇6) 3 ·〇 7 ( 4 Η，m )， 3 · 8 6 ( 3 Η，s )， 4 · 1 9 ( 2 Η，t )， 5.66(2H，s)， r 7 · 1 0 ( 1 H，d )， 7 · 1 4 ( 2 H，m )， 7 · 7 8 ( 1 H，d )， 8 · 0 6 ( 1 H，d )， 8 · 6 6 ( 1 H，s )， l〇.45(lH，s)。 L R M S ： m / z 595 (M+1)+。 實施例6 7 5 —〔5— (4 —乙基六氫吡畊一 1—基磺醯基）2 一正丙氧苯基〕一 2 —（3 —甲氧吼陡一2 —基）甲基一 2，6 —二氫一7H —吡唑並〔4，3 — d〕嘧啶一 7 — 酮 經濟部中央標準局員工消費合作社印製 (請先閱讀背面之注意事項再填寫本頁) 由製備例4 8之標題化合物及1 -乙基六氫吡啡依實 施例1之步驟製得，呈白色固體（85%)。 元素分析實測値C，5 8 · 1 9 ; Η，6 · 4 9 ; N，1 5 · 62。C3〇H39N7〇5S ；〇· 50H2〇計算値 C ，58.23 ;Η，6·52;Ν，15.85%。 5 ( C D C 1 3 ) :0.98 (6H，m)， 1 · 1 0 ( 3 H ， t )， 本纸張尺度適用中國國家標準（CNS ) A4規格（210X297公釐）-1〇9 - 524805 B7 五、發明説明（1〇7) 1 · 7 8 ( 2 Η，m )， 1 · 9 8 ( 2 Η，m )， 2 · 3 7 ( 2 Η，q )， 2 · 5 0 ( 4 Η，m )， 2 · 8 6 ( 2 Η，t )， 3 ·〇 7 ( 4 Η，m )， 3 · 8 4 ( 3 Η，s )， 4 . 1 9 ( 2 Η，t )， 5 · 6 7 ( 2 Η，s )， 7 · 1 0 ( 1 Η，d )， 7 · 1 5 ( 2 Η，m )， 7 · 6 8 ( 1 Η，d )， 8 · 0 6 ( 1 Ή，d )， 8 · 7 7 ( 1 Η，s )， 1 0 · 4 4 ( 1 Η，s )。 LRMS:m/z 610(M+1)+。 經濟部中央標準局員工消費合作社印製 (請先閱讀背面之注意事項再填寫本頁) 實施例6 8 2— (6 —胺基吼π定—2 —基）甲基一5 —〔5 —( 4 一乙基六氫吡畊一 1 一基磺醯基）一 2 —正丙氧苯基〕 —3 —正丙基—1，6 -二氫—7Η -吡唑並〔4，3-d〕嘧啶一 7 -酮 由製備例4 9之標題化合物依實施例1之步驟製得， 呈白色固體（30%)。 本纸張尺度適用中國國家標準（CNS ) A4規格（210X297公釐） 一 524805 ΑΊ Β7 五、發明説明（1〇8) 元素分析實測値：C，5 8 · 2〇；Η，6 · 6 1 ; Ν， 經濟部中央標準局員工消費合作社印製 Η l· 1 9 2 QU C . 〇 7 7 5τ ， . C 7 値 1 算 Ν Η 〇 6 ο 〇、 1T This paper size applies the Chinese National Standard (CNS) A4 specification (210X297 mm) _ 107-524805 B7_ V. Description of the invention (105) 7 · 6 3 (1 Η, m), 7 · 8 6 (1 Η, d), 8 · 5 9 (1 Η, d), 8 · 8 0 (1 Η, s), 10.62 (lH, s). L R M S: m / z 609 (M + 1) +. Example 6 6 2 — (3-methoxypyridin-2-yl) methyl-5— [5 — (4-methylhexahydropyridine-1 1-ylsulfonyl) 2-n-propoxyphenyl] -3-n-propyl-2, 6--* hydrogen /-7H-hydrazine [4,3 — d] chelate D 7-7 ketone from the title compound of Preparation Example 4 8 and 1 -methylhexahydro Pycnogenol was prepared according to the procedure of Example 1 as a white solid (82%). Elemental analysis: 値: C, 5 7 · 60; Η, 6 · 2 3; N, 15 · 92. C29H37N7〇5S; 0.550H20 calculated 値 C, 57. 60; Η, 6.33; N, 16.21%. Printed by the Consumer Cooperatives of the Central Standards Bureau of the Ministry of Economic Affairs (please read the precautions on the back before filling out this page) 5 (CDC 1 3): 0,94 (3H, t), 1 · 09 (3H, t), 1 · 7 8 (2 H, m), 1 · 9 8 (2 H, m), 2 · 2 3 (3 H, s), 2 · 4 4 (4 H, m), 2 · 9 6 (2 H, t), this paper size applies Chinese National Standard (CNS) A4 specification (210X29? Mm)-108 524805 A7 B7 V. Description of the invention (1 06) 3 · 07 (4 Η, m) , 3 · 8 6 (3 Η, s), 4 · 1 9 (2 Η, t), 5.66 (2H, s), r 7 · 1 0 (1 H, d), 7 · 1 4 (2 H, m), 7 · 7 8 (1 H, d), 8 · 0 6 (1 H, d), 8 · 6 6 (1 H, s), 10.45 (1 H, s). L R M S: m / z 595 (M + 1) +. Example 6 7 5-[5-(4-ethylhexahydropyridine-1-sulfosulfanyl) 2-n-propoxyphenyl]-2-(3-methoxymethoxy 2- 2-yl) methyl Base-2,6-dihydro-7H-pyrazolo [4,3-d] pyrimidine-7-one Printed by the Consumer Cooperatives of the Central Standards Bureau of the Ministry of Economic Affairs (Please read the precautions on the back before filling out this page) by The title compound of Preparation 48 and 1-ethylhexahydropyridine were prepared according to the procedures of Example 1 as a white solid (85%). Elemental analysis: 値 C, 5 8 · 19; Η, 6 · 4 9; N, 1 · 62. C3OH39N705S; 0.550H2O calculated C, 58.23; H, 6.52; N, 15.85%. 5 (CDC 1 3): 0.98 (6H, m), 1 · 10 (3 H, t), this paper size is applicable to China National Standard (CNS) A4 specification (210X297 mm) -109-524805 B7 V. Description of the invention (107) 1 · 7 8 (2 Η, m), 1 · 9 8 (2 Η, m), 2 · 3 7 (2 Η, q), 2 · 5 0 (4 Η, m), 2 · 8 6 (2 Η, t), 3 · 07 (4 Η, m), 3 · 8 4 (3 Η, s), 4. 1 9 (2 Η, t), 5 · 6 7 (2 Η, s), 7 · 1 0 (1 Η, d), 7 · 1 5 (2 Η, m), 7 · 6 8 (1 Η, d), 8 · 0 6 (1 Ή, d ), 8 · 7 7 (1 Η, s), 1 0 · 4 4 (1 Η, s). LRMS: m / z 610 (M + 1) +. Printed by the Consumer Cooperatives of the Central Bureau of Standards of the Ministry of Economic Affairs (please read the precautions on the back before filling this page) Example 6 8 2— (6 —Amine group — 2 —yl) Methyl 5 — [5 — (4 monoethylhexahydropyridine-1 monosulfofluorenyl) -2 2-n-propoxyphenyl] 3 -n-propyl-1,6-dihydro-7—-pyrazolo [4,3- d] Pyrimidine-7-one was prepared from the title compound of Preparation 4-9 according to the procedure of Example 1 as a white solid (30%). This paper size applies to Chinese National Standard (CNS) A4 (210X297 mm)-524805 ΑΊ Β7 V. Description of the invention (108) Elemental analysis and actual measurement 値: C, 5 8 · 2〇; Η, 6 · 6 1 Ν, printed by the Consumer Cooperatives of the Central Bureau of Standards of the Ministry of Economic Affairs Η l · 192 2 QU C. 〇7 7 5τ,. C 7 値 1 counts Ν Η 〇6 ο 〇

ο 5 y \]y \)/ )/ \ly \J )y s 5 tttmmtmt s sddmd s s ， ux1 \)/ Tu Ji Ji Ji J1 Ji Ji Ji Ji TT- Ji TT- Ji TTX THX TT- / 3TrTrTTTrTrTh-TrTrTrTrTrTrxuiTrTrf - - / 13222424222111111( m ο /(V /IV /fv /{V xiv /(V κί\ Γν /(ν /(V Γν /IV Γν /(\ /(ν /l\ 00 ·. D89426905280553905S C17 0 4591244313875 M /—V · · ··· · · · · · ··· · c .u 511222234456777781L \My \)/ 3 2Η c 8 〇 1 6• Ν ο ; • ’ 3s 6 計Η 〇 5 % \)/ mΗ 6 + Μ 本紙張尺度適用中國國家標準（CNS ) A4規格（210'乂 297公釐）-111 - (請先閲讀背面之注意事項再填寫本頁) 524805 hi B7 五、發明説明（1〇9) 實施例6 9 2 — (1—甲基味哩一2 —基）甲基一 5 —〔5 —( 4一甲基六氫吡畊一1一基磺醯基）一2—正丙氧苯基〕 —3 —正丙基—2，6 —二氫—7H -吡唑並〔4，3 -d〕嘧D定一 7 -酮 由製備例5 2之標題化合物及1 -甲基六氫吡畊依實 施例1之步驟製得，呈白色泡沬狀（5 2 % )。 (5 ( C D C 1 3 ):〇·96(3Η，ΐ)， 1 . 1 4 ( 3 Η ， t )， (請先閲讀背面之注意事項再填寫本頁) λ]/ \)/ 經濟部中央標準局員工消費合作社印製ο 5 y \] y \) /) / \ ly \ J) ys 5 tttmmtmt s sddmd ss, ux1 \) / Tu Ji Ji Ji J1 Ji Ji Ji Ji TT- Ji TT- Ji TTX THX TT- / 3TrTrTTTrTrxxTrTruiui --/ 13222424222111111 (m ο / (V / IV / fv / (V xiv / (V κί \ Γν / (ν / (V Γν / IV Γν / (\ / (ν / l \ 00 · D89426905280553905S C17 0 4591244313875 M / -V · · · · · · · · · · · · · · c .u 511222234456777781L \ My \) / 3 2Η c 8 〇1 6 • Ν ο; • '3s 6 count Η 〇5% \) / mΗ 6 + Μ This paper size applies Chinese National Standard (CNS) A4 specification (210 '乂 297mm) -111-(Please read the precautions on the back before filling this page) 524805 hi B7 V. Description of the invention (1〇 9) Example 6 9 2-(1-Methyltriazol-2-yl) methyl-5-[5-(4-methylhexahydropyridine-11-ylsulfonyl) -2-n-propyl Oxyphenyl] —3-n-propyl-2,6-dihydro-7H-pyrazolo [4,3-d] pyrimidin-7-one From the title compound of Preparation Example 2 and 1-methyl Hexahydropyridine was prepared according to the procedure of Example 1 and was white foamy (52%). (5 (CDC 1 3): 〇 · 96 (3Η, ΐ), 1. 1 4 (3 Η, t), (Please read the precautions on the back before filling out this page) λ] / \) / Printed by the Staff Consumer Cooperative of the Central Standards Bureau of the Ministry of Economic Affairs

〇 9 \ily y \)y \)y \ly \ly \)/ \)/ s 5 mmsmmstsssdds ， II. 一 hhhhhhhhhhhhhi/ 2234632211111( m χί\ /fv /vv /IV /{V /IV /V /(V /IV κ(ν /(V ov · · 52 -600547604266S 7025 1 72680187 M • · · · · · ··· ····(Ky 12223345677781L \)/ \)y +Μ 本纸張尺度適用中國國家標準（CNS ) Α4規格（210X 297公釐）_ 112 - 524805 A7 B7 五、發明説明（110) 實施例7 0 5 —〔5 —（4 一乙基六氫吡畊—1—基磺醯基）〜 2 —正丙氧苯基〕一 2— (1 —甲基咪哩一2 —基）甲基 —3 —正丙基—2，6 -二氫一 7H —吡唑並〔4， d〕嘧啶一 7 -酮 由製備例5 2之標題化合物及1 -乙基六氫吡哄依實 施例1之步驟製得，呈白色固體（7 0 % )。 元素分析實測値：C，5 6 · 6 7 ; Η，6 · 6 5 ; N， 18 · 54。C28H38N8〇4S ; 〇 · 60H2 呈白色泡 沫狀計算値C，5 6 · 6 6 ; Η，6 · 6 6 ; Ν，1 8 · 8 8 %。 5 ( C D C 1 3 ) :1·00(6Η，πι)， (請先閱讀背面之注意事項再填寫本頁} 經濟部中央標準局員工消費合作社印製 \)/ nm/ \)/ \)x N)/ \1/ N)/ N)y \ly tmmQmmstsss J1 Ji THX Jl J1 Ji Ji J1 XHA THX Tu Tr- Th- TF -ul TF ΤΓ. TL1 ΤΓ ΤΓ ΤΓ ΤΓ 32224632211 rv /fv /(V /IV /(V /IV /IV /IV/^' /{V /{V 66302083860 17045172680 ··♦·····♦·· 11222334567 本紙張尺度適用中國國家標準（CNS ) A4規格（210X297公釐）-113 - 524805 A7 B7 五、發明説明（111) 7 · 1 4 ( 1 Η，d )， 7 · 8 4 ( 1 Η，d )， 8 · 7 7 ( 1 Η，s )， 10.6〇（lH，s)。 L R M S ： m / z 583 (M+1)+。 實施例7 1 5— { 5 —〔4 — (2 —經乙基）六氣吼哄一 1—基 磺醯基〕—2 -正丙氧苯基} 一 2 - (1—甲基咪唑—2 —基）甲基一 3 —正丙基一 2，6 -二氫一 7H —吡唑並 〔4，3 - d〕嘧啶一 7 -酮 由標題化合物5 2之標題化合物及1 一（ 2 -羥乙基 )六氫吡畊依實施例1之步驟製得，呈白色固體（3 1 % )° 5 ( C D C 1 a ) :0.98(3H，t) ， 1 · 1 4 ( 3 Η，t )， 2 · 7 4 ( 2 Η，m )， 經濟部中央標準局員工消費合作社印製 (請先閲讀背面之注意事項再填寫本頁) 2 ·〇 4 ( 2 Η，m )， 2 · 3 2 ( 1 Η，s )， 2 · 5 4 ( 2 Η，t )， 2 · 6 〇（4 Η，m )， 3 . 1 2 ( 6 Η，m )， 3 · 5 6 ( 2 Η，m )， 3 · 7 6 ( 3 Η ， s )， 本纸張尺度適用中國國家標準（CNS ) A4規格（210X297公釐）_ 114 _ 524805 A7 __ B7 五、發明説明（112) 4 · 2 4 ( 2 Η，t )， 5 · 6 6 ( 2 Η，s )， (請先閱讀背面之注意事項再填寫本頁) 6 · 8 4 ( 1 Η，s )， 7 ·〇〇（1 Η ， s )， 7 · 1 5 ( 1 Η，d )， 7 · 8 2 ( 1 Η，d )， 8 · 7 5 ( 1 Η，s )， l〇.62(lH，s) ° LRMS:m/z 599(M+1)+。 實施例7 2 5 —〔5 —（4 一胺羰基甲基六氫吡畊一 1—基磺醯 基）一 2 -正丙氧苯基〕—1— (1—甲基咪唑一2 —基 )甲基一 3 —正丙基一 2，6 —二氫—7H —吡唑並〔4 ，3 — d〕嘧啶—7 -酮 由製備例5 1之標題化合物及1 -胺羰基甲基六氫吡 畊（Indian J. Chem.，1984，23JB., 650 )依實施例 1 之步驟 經濟部中央標準局員工消費合作社印製 澧 SB 固 色 白 呈 得 製 % 7〇9 \ ily y \) y \) y \ ly \ ly \) / \) / s 5 mmsmmstsssdds, II. Hhhhhhhhhhhhhi / 2234632211111 (m χί \ / fv / vv / IV / {V / IV / V / ( V / IV κ (ν / (V ov · · 52 -600547604266S 7025 1 72680187 M · · · · · · · · · · (Ky 12223345677781L \) / \) y + M This paper size applies to China Standard (CNS) A4 specification (210X 297 mm) _ 112-524805 A7 B7 V. Description of the invention (110) Example 7 0 5 — [5 — (4 monoethylhexahydropyridine — 1-sulfosulfanyl) ) ~ 2 -n-propoxyphenyl]-2-(1-methylimido-2 -yl) methyl-3 -n-propyl-2,6-dihydro-7H -pyrazolo [4, d ] Pyrimidine-7-one was prepared from the title compound of Preparation Example 52 and 1-ethylhexahydropyridine according to the procedure of Example 1. It was a white solid (70%). Elemental analysis found: C, 5 6 · 6 7; Η, 6 · 6 5; N, 18 · 54. C28H38N8〇4S; 〇 · 60H2 Calculate as white foam 値 C, 5 6 · 6 6; Η, 6 · 6 6; Ν, 1 8 · 8 8%. 5 (CDC 1 3): 1 · 00 (6Η, π), (Please read the precautions on the back before filling in this page } Printed by the Consumer Cooperatives of the Central Bureau of Standards of the Ministry of Economic Affairs \) / nm / \) / \) x N) / \ 1 / N) / N) y \ ly tmmQmmstsss J1 Ji THX Jl J1 Ji Ji J1 XHA THX Tu Tr- Th- TF -ul TF ΤΓ. TL1 ΤΓ ΤΓ ΤΓ ΤΓ 32224632211 rv / fv / (V / IV / (V / IV / IV / IV / ^ '/ {V / {V 66302083860 17045172680 ········ ♦ ·· 11222334567 This paper size applies to Chinese National Standard (CNS) A4 (210X297 mm) -113-524805 A7 B7 V. Description of the invention (111) 7 · 1 4 (1 Η, d), 7 · 8 4 ( 1Η, d), 8 · 7 7 (1 1, s), 10.6 (lH, s). L R M S: m / z 583 (M + 1) +. Example 7 1 5— {5 — [4 — (2 —Ethyl) hexazine] coaxing a 1-sulfosulfanyl group] 2 -n-propoxyphenyl} 2-(1 -methylimidazole- 2-yl) methyl-1,3-n-propyl-2,6-dihydro-7H-pyrazolo [4,3-d] pyrimidin-7-one from the title compound 5 and the title compound 1 and 2 (2 -Hydroxyethyl) hexahydropyridine, prepared according to the procedure of Example 1, as a white solid (31%) ° 5 (CDC 1 a): 0.98 (3H, t), 1 · 1 4 (3 Η, t ), 2 · 7 4 (2 Η, m), printed by the Consumer Cooperatives of the Central Standards Bureau of the Ministry of Economic Affairs (please read the notes on the back before filling out this page) 2 · 〇4 (2 Η, m), 2 · 3 2 (1 Η, s), 2 · 5 4 (2 Η, t), 2 · 6 〇 (4 Η, m), 3. 1 2 (6 Η, m), 3 · 5 6 (2 Η, m ), 3 · 7 6 (3 Η, s), this paper size applies Chinese National Standard (CNS) A4 (210X297 mm) _ 114 _ 524805 A7 __ B7 V. Description of the invention (112) 4 · 2 4 ( 2 Η, t), 5 · 6 6 (2 Η, s), (Please read the notes on the back before filling out this page) 6 · 8 4 (1 Η, s), 7 · 〇〇 (1Η, s), 7.15 (1 1, d), 7.82 (1Η, d), 8.75 (1Η, s), 10.62 (lH, s ) ° LRMS: m / z 599 (M + 1) +. Example 7 2 5 — [5 — (4-monoaminocarbonylmethylhexahydropyridine-1—ylsulfonyl) —2-n-propoxyphenyl] -1- (1-methylimidazol-2-yl ) Methyl-3-n-propyl-2,6-dihydro-7H-pyrazolo [4,3-d] pyrimidin-7-one was prepared from the title compound of Preparation 51 and 1-aminocarbonylmethylhexa Hydropyridine (Indian J. Chem., 1984, 23JB., 650) According to the procedure of Example 1, printed by the Central Consumers Bureau of the Ministry of Economic Affairs, Consumer Cooperatives, 澧 SB, solid color, white.

ο ο NJ \)/ \)y Γ-丄: tmmmt THX Ji THX THX XHX 3 ΤΓ ΤΓ ΤΓ ΤΓ rr 1 3 2 2 4 2 c r\ /IV /v\ /IV r\ D 8 6 o 8 2 c 1 8 o 6 9 X—\ ····· IX t—I CN1 CN1 CXI H 3 本纸張尺度適用中國國家標準（CNS ) A4規格（210X297公釐）-115 - 524805 A7 經濟部中央標準局員工消費合作杜印製 B7五、發明説明（113) 3 ·〇 4 ( 2 Η，s )， 3 · 1 4 ( 4 Η，m )， 3 · 7 8 ( 3 Η，s )， 4 · 2 8 ( 2 Η，t )， 5 · 3 7 ( 1 Η，s )， 5 . 9 〇（2 Η，s )， 6 · 6 6 ( 1 Η，s )， 6 · 8 6 ( 1 Η，s )， 7 ·〇 0 ( 1 Η，s )， 7 . 1 8 ( 1 Η，d )， 7 · 8 7 ( 1 Η，d )， 8 · 8 4 ( 1 Η，s )， 1〇·9〇（1ϋ，3)° LRMS:m/z 612(M+1)+。 實施例7 3 2 —（3，5 —二甲基異哼唑一4 —基）甲基一5 — 〔5 —（4 —甲基六氫吡畊一 1 一基磺醯基）一 2 -正丙 氧苯基〕一 3 —正丙基—2，6 —二氫—7H —吡唑並〔 4，3 — d〕嘧啶一 7 —酮 由製備例5 5之標題化合物及1 -甲基六氫吡畊依實 施例1之步驟製得，呈白色泡沬狀（3 4 % )。 元素分析實測値C，5 7 · 1 9 ; Η，6 · 3 7 ; Ν， 16 · 19 。C28H37N7〇5S ； 〇 · 35H2〇計 (請先閱讀背面之注意事項再填寫本頁) 本紙張尺度適用中國國家標準（ CNS ) A4規格（210Χ297公釐）-116 _ 經濟部中央標準局員工消費合作社印製 524805 A7 B7 五、發明説明（114) 算値C，56.82;H，6.42;N， 16.66% 〇 ά ( C D C 1 3 ) :0.98(3H，t)， 1 · 1 4 ( 3 H，t )， 1.78(2H，m)， 2 · 0 2 ( 2 H，m )， 2 · 1 6 ( 3 H，s )， 2 · 2 4 ( 3 H，s )， 2 · 3 5 ( 3 H，s )， 2 . 4 6 ( 4 H，m )， 2 · 9 0 ( 2 H，t )， 3 · 5 7 ( 4 H，m )， 4 · 2 3 ( 2 H，t )， 5 · 2 8 ( 2 H，s )， 7 · 1 4 ( 1 H，d )， 7 · 8 0 ( 1 H，d )， 8 · 7 4 ( 1 H，s )， l〇.64(lH，s)。 LRMS:m/z 584(M+1)+。 實施例7 4 5— {5 —〔4一（2 —羥乙基）六氫吡畊一 1—基 磺醯基〕一 2 —正丙氧苯基} 一 2 -（3，5 -二甲基咪 唑一 4 一基）甲基一 3 —正丙基—2，6 —二氫—7H — 本紙張尺度適用中國國家標準（CNS ) A4規格（210X 297公釐）-117 - (請先閱讀背面之注意事項再填寫本頁)ο ο NJ \) / \) y Γ- 丄: tmmmt THX Ji THX THX XHX 3 ΤΓ ΤΓ ΤΓ ΤΓ rr 1 3 2 2 4 2 cr \ / IV / v \ / IV r \ D 8 6 o 8 2 c 1 8 o 6 9 X— \ ····· IX t—I CN1 CN1 CXI H 3 This paper size applies to China National Standard (CNS) A4 (210X297 mm) -115-524805 A7 Employees of the Central Standards Bureau of the Ministry of Economic Affairs Consumption Cooperation Du printed B7 V. Invention Description (113) 3 · 〇4 (2 2, s), 3 · 1 4 (4 Η, m), 3 · 7 8 (3 Η, s), 4 · 2 8 (2 Η, t), 5 · 3 7 (1 Η, s), 5.9 〇 (2 Η, s), 6 · 6 6 (1 Η, s), 6 · 8 6 (1 Η, s) , 7 · 〇0 (1 Η, s), 7. 1 8 (1 Η, d), 7 · 8 7 (1 Η, d), 8 · 8 4 (1 Η, s), 1 · 9〇 (1ϋ, 3) ° LRMS: m / z 612 (M + 1) +. Example 7 3 2 — (3,5—dimethylisohumidazole—4-yl) methyl—5— [5— (4-methylhexahydropyridine—1—sulfosulfanyl) —2— N-propoxyphenyl] -3-n-propyl-2,6-dihydro-7H-pyrazolo [4,3-d] pyrimidin-7-one was prepared from the title compound of Preparation 5 and 1-methyl Hexahydropyridine was prepared according to the procedure of Example 1 and was white foamy (34%). Elemental analysis: 値 C, 5 7 · 19; Η, 6 · 3 7; Ν, 16 · 19. C28H37N7〇5S; 〇 · 35H2〇 meter (please read the precautions on the back before filling in this page) This paper size is applicable to China National Standard (CNS) A4 specification (210 × 297 mm) -116 _ Employee Consumer Cooperative of the Central Standards Bureau of the Ministry of Economic Affairs Printed 524805 A7 B7 V. Description of the invention (114) Calculation of C, 56.82; H, 6.42; N, 16.66% (CDC 1 3): 0.98 (3H, t), 1 · 1 4 (3 H, t ), 1.78 (2H, m), 2 · 0 2 (2 H, m), 2 · 1 6 (3 H, s), 2 · 2 4 (3 H, s), 2 · 3 5 (3 H, s), 2. 4 6 (4 H, m), 2 · 9 0 (2 H, t), 3 · 5 7 (4 H, m), 4 · 2 3 (2 H, t), 5 · 2 8 (2 H, s), 7 · 1 4 (1 H, d), 7 · 8 0 (1 H, d), 8 · 7 4 (1 H, s), 10.64 (1 H, s) . LRMS: m / z 584 (M + 1) +. Example 7 4 5— {5— [4-((2-hydroxyethyl) hexahydropyridine—1-sulfofluorenyl] —2-n-propoxyphenyl}} 2— (3,5-dimethyl Imimidazole-1, 4-yl) methyl-1, 3-n-propyl-2, 6-dihydro-7H — This paper size applies to Chinese National Standard (CNS) A4 (210X 297 mm) -117-(Please read first (Notes on the back then fill out this page)

524805 五、發明説明（115) 吼ΰ坐並〔4，3 - d〕嘧(J定一 7 -酮 由製備例55之標題化合物及1一（2-羥乙基）六 體固色白 呈 得 製 驟 步 之 1-1 例 施 實 依 哄 吼 氣 經濟部中央標隼局員工消費合作社印製 値 cl 3 HHHHHHHHHHHHHHHH1 測 〇 413CXI231324242CX12111C {貫 〇 · C κίν cv Γν /IV κ(\ Γ\ /ι\ Γν Γν /{V /IV /(V /IV /IV /IV 5 析 56D 5 84828400876 0 8276 分 . ， C1701335690523187 素 5HC··· ······ ·······0 一兀 1 ; 511222222233457781 c Η Ν \ly \)/ \)/ \)/ \)/ \)/ \)/ \)/ \)/ \)/ \)y \)/ \)/ \)/ tmmssstmtmmtsdd524805 V. Description of the invention (115) Sit down with [4,3-d] pyrimidine (J-a-7-one from the title compound of Preparation 55 and 1- (2-hydroxyethyl) hexasodium color fixing white 1-1 of the steps in the manufacturing process Shi Shiyi printed the print of the employee consumer cooperative of the Central Bureau of Standards of the Ministry of Economic Affairs cl 3 HHHHHHHHHHHHHHHH1 Test 413CXI231324242CX12111C {〇〇 C κίν cv Γν / IV κ (\ Γ \ / ι \ Γν Γν / {V / IV / (V / IV / IV / IV 5 analysis 56D 5 84828400876 0 8276 points., C1701335690523187 prime 5HC ················ 1 511222222233457781 c Η Ν \ ly \) / \) / \) / \) / \) / \) / \) / \) / \) / \) y \) / \) / \) / tmmssstmtmmtsdd

5 15)Ν ο 5 J 1—I ο 3 6 C，値t) Η 算。，計FH 8 S 8 。 ， 5 λ)/ N T 96;. ^—- 4 6 3 4 5 (請先閱讀背面之注意事項再填寫本頁) Η5 15) N ο 5 J 1—I ο 3 6 C, 値 t) 算. Count FH 8 S 8. , 5 λ) / N T 96 ;. ^ —- 4 6 3 4 5 (Please read the precautions on the back before filling this page) Η

S 本紙張尺度適用中國國家標準（CNS ) A4規格（210X 297公釐）-118 - 524805 ΑΊ Β7 五、發明説明（116) L R M S ： m / z 614(M+1)+。 實施例7 5 5 —〔2 —乙氧一5— (4 —甲基六氫吡畊一 1—基 磺醯基）苯基〕一3 —甲基一2 -（2 —曱基噻唑—4 — 基）甲基一2，6 —二氫一7H —吡唑並〔4，3 — d〕 嘧陡一 7 -酮 由製備例5 7之標題化合物及1 -甲基六氫吡畊依實 施例1之步驟製得，呈白色固體C 8 0 % )。 元素分析實測値·· C，5 2 · 5 2 ; Η，5 · 4 0 ; N， 17 . 54。C24H29N7〇4S2 計算値 (請先閱讀背面之注意事項再填寫本頁) 經濟部中央標準局員工消費合作社印製 2 3ΗΗΗΗΗΗΗΗΗΗΗ 0134334221111 • /' /(\ /ι\ /IV /(\ /IV /IV /IV /IV /(V /(V 3D68680682420 5C24661359188 ， /—\·_*·♦·*·*♦· C522223456778 N 8 3 5 Η 8 % 3 〇 Η 3 /ι\ ο 6 1 smssmQssdds 本紙張尺度適用中國國家標準（CNS ) Α4規格（210Χ 297公釐）_ 119 - 524805 kl B7 五、發明説明（117) 10.52(lH，s)° LRMS:m/z 544 (M+1)+。 實施例7 6 5 —〔5 —（4 —甲基六氯吼哄一 1—基礦酸基）— 2 —正丙氧苯基〕一 2 —（2 —甲基噻唑一 4 一基）甲基 —3 —正丙基—2，6 —二氫一 7H -吡唑並〔4，3 — d〕嘧啶一 7 -酮 由製備例5 8之標題化合物及1 -甲基六氫吡畊依實 施例1之步驟製得，呈白色泡沬狀（4 3 % )。 元素分析實測値：C，5 5 · 4 2 ; Η，6 · 1 3 ; N， 16 . 24。C27H35N7〇4S2 計算値 C，55.36 ;Η，6·02 ;N，16.74%。 5(CDCl3):1.0〇（3H，t)， 1 · 1 5 ( 3 Η，t )， · 1 · 8 2 ( 2 Η，m )， 2 . 0 4 ( 2 H ^ m )， 經濟部中央標準局員工消費合作社印製 (請先閱讀背面之注意事項再填寫本頁) 2 · 2 7 ( 3 H，s )， 2 · 5 0 ( 4 H，m )， 2 · 7 〇（3 H，s )， 3 ·〇 5 ( 2 H，t )， 3 · 1 〇（4 H，m )， 4 · 2 4 ( 2 H，t )， 5 · 6 2 ( 2 H，s )， 本紙張尺度適用中國國家標準（〇奶）六4規格（210乂 297公楚）-12〇 - 524805 ΡκΊ Β7 五、發明説明（118) 6 · 9 0 ( 1 Η，s )， 7 · 1 6 ( 1 Η，d )， (請先閱讀背面之注意事項再填寫本頁) 7 · 8 2 ( 1 Η，d )， 8 · 7 8 ( 1 Η，s )， <10.58(lH，s)° L R M S ： m / z 586 (M+1)+。 實施例7 7 5 —〔5 —（4 一甲基六氫吡啡一 1 一基磺醯基）一 2 —正丙氧苯基〕—2 — (1—甲基一 1，2，4 —三唑 —5 —基）甲基—3 —正丙基—2 ’ 6 — —•氨一 7H — D比 唑並〔4，3 — d〕嘧啶一 7 —酮 由製備例6 0之標題化合物及1 -甲基六氫吡畊依實 施例1之步驟製得，呈白色固體（44%)。 ά ( C D C 1 a ) :1.0〇（3H，t)， 1 · 1 6 ( 3 Η，t )， 1 . 8 2 ( 2 Η ，m )， 經濟部中央標準局員工消費合作社印製 hhhhhhh 2 3 4 6 3 2 2 /IV /IV /' /IV /(V /(\ /V 4 7 8 0 2 6 〇 0 2 4 1 0 2 7 ······· 2 2 2 3 4 4 5 m s m m s t s \)y \)y 本纸張尺度適用中國國家標準（CNS ) A4規格（210X 297公釐）-121 - 524805 A7 B7五、發明説明（119) 7.15(lH，d)， . 7 · 8 4 ( 2 Η，m )， 8 · 7 6 ( 1 Η，d )， l〇.63(lH，s)。 LRMS:m/z 570 (M+1)+。實施例7 8 5 —〔5 —（4 —乙基六氫吼哄—1 一基礦釀基）一 2 —正丙氧苯基〕一2 — (1 —甲基—1，2，4 —三唑 —5 —基）甲基一3 —正丙基—2，6 —二氫一7H —吡 唑並〔4，3 — d〕嘧啶—7 -酮 由製備例6 0之標題化合物及1 -乙基六氫吡畊依實 施例1之步驟製得，呈白色固體（8 3 % )。 元素分析實測値：C，5 4 · 7 6 ; Η，6 · 3 6 ; N， 2 1 · 0 5 。C 2 7 Η 3 7 Ν 9 〇 4 S ; 0 · 5 0 Η 2 〇計算値 經濟部中央標準局員工消費合作社印製 2 2 2 3 4 t—- 3HHHHHHH 713222463 . c κ' κίν ^\ /l\ rv /{\ r\ 4D5040422 5C1804510 2 Ν 6 4 6 Η m Η 6 /(\ ο 〇 \)y \)/ Ν)/ \iy \j, m m q m m s % 7 2 (請先閲讀背面之注意事項再填寫本頁)S This paper size is in accordance with Chinese National Standard (CNS) A4 specification (210X 297 mm) -118-524805 ΑΊ Β7 V. Description of the invention (116) L R M S: m / z 614 (M + 1) +. Example 7 5 5 — [2-Ethoxy-5— (4-methylhexahydropyridine—1-sulfofluorenyl) phenyl] —3-Methyl-2— (2-fluorenylthiazole—4 —Methyl) methyl-2,6-dihydro-7H-pyrazolo [4,3 — d] Pyridoxone-7-one was carried out from the title compound of Preparation Example 5 7 and 1-methylhexahydropyridine It was obtained by the procedure of Example 1 as a white solid (C80%). Elemental analysis: 値 ·· C, 5 2 · 5 2; Η, 5 · 4 0; N, 17. 54. C24H29N7〇4S2 Calculation 値 (Please read the notes on the back before filling this page) Printed by the Consumer Cooperatives of the Central Standards Bureau of the Ministry of Economic Affairs 2 3 ΗΗΗΗΗΗΗΗΗΗΗ 0134334221111 • / '/ (\ / ι \ / IV / (\ / IV / IV / IV / IV / (V / (V 3D68680682420 5C24661359188, / — \ · _ * · ♦ · * · * ♦ · C522223456778 N 8 3 5 Η 8% 3 〇Η 3 / ι \ ο 6 1 smssmQssdds National Standard (CNS) A4 specification (210 × 297 mm) _ 119-524805 kl B7 V. Description of the invention (117) 10.52 (lH, s) ° LRMS: m / z 544 (M + 1) +. Example 7 6 5 — [5 — (4-methylhexachloromethyl) — 1 —yloxy acid — 2 —n-propoxyphenyl] — 2 — (2-methylthiazole — 4-yl) methyl — 3 — N-propyl-2,6-dihydro-7H-pyrazolo [4,3-d] pyrimidin-7-one was prepared from the title compound of Preparation Example 5 8 and 1-methylhexahydropyridine according to Example 1 It was prepared in the step and showed a white bubble-like shape (43%). Elementary analysis measured 値: C, 5 5 · 4 2; Η, 6 · 1 3; N, 16. 24. C27H35N704 · S2 Calculate 値 C, 55.36; No, 6.02; N, 16.74%. 5 (CD Cl3): 1.00 (3H, t), 1 · 1 5 (3 t, t), · 1 · 8 2 (2 Η, m), 2.0 4 (2 H ^ m), Central Bureau of Standards, Ministry of Economic Affairs Printed by the employee consumer cooperative (please read the notes on the back before filling out this page) 2 · 2 7 (3 H, s), 2 · 50 0 (4 H, m), 2 · 7 〇 (3 H, s) , 3 · 05 (2 H, t), 3 · 1 0 (4 H, m), 4 · 2 4 (2 H, t), 5 · 6 2 (2 H, s), this paper scale applies to China National Standard (〇 奶) 六 Specification (210 乂 297 公 楚) -12〇- 524805 ΡκΊ Β7 V. Description of the invention (118) 6 · 9 0 (1 Η, s), 7 · 1 6 (1 Η, d ), (Please read the notes on the back before filling this page) 7 · 8 2 (1 Η, d), 8 · 7 8 (1 Η, s), < 10.58 (lH, s) ° LRMS: m / z 586 (M + 1) +. Example 7 7 5 — [5 — (4-methylhexahydropyridine-1, 1-sulfofluorenyl), 2-n-propoxyphenyl] -2 — (1-methyl-1, 2, 4, — Triazol-5-yl) methyl-3-n-propyl-2'6 — — • Ammonia-7H —D-pyrazolo [4,3 — d] pyrimidin-7-one was prepared from the title compound of Preparation Example 6 0 And 1-methylhexahydropyridine was prepared according to the procedure of Example 1 as a white solid (44%). ά (CDC 1 a): 1.00 (3H, t), 1 · 1 6 (3 Η, t), 1. 8 2 (2 Η, m), printed by the Consumer Cooperatives of the Central Standards Bureau of the Ministry of Economic Affairs hhhhhhh 2 3 4 6 3 2 2 / IV / IV / '/ IV / (V / (\ / V 4 7 8 0 2 6 〇 0 2 4 1 0 2 7 ······ 2 2 2 3 4 4 5 msmmsts \) y \) y This paper size applies Chinese National Standard (CNS) A4 specification (210X 297mm) -121-524805 A7 B7 V. Description of the invention (119) 7.15 (lH, d),. 7 · 8 4 (2 Η, m), 8 · 7 6 (1 Η, d), 10.63 (1H, s). LRMS: m / z 570 (M + 1) +. Example 7 8 5 — [5 — (4-ethylhexahydrozine-1—one-based mineral group) —2—n-propoxyphenyl] —2— (1—methyl-1, 2, 4— Triazol-5-yl) methyl-1,3-n-propyl-2,6-dihydro-7H-pyrazolo [4,3-d] pyrimidin-7-one was prepared from the title compound of Preparation Example 6 and 1 -Ethylhexahydropyridine was prepared according to the procedure of Example 1 as a white solid (83%). Elemental analysis: 値: C, 5 4 · 7 6; Η, 6 · 3 6; N, 2 1 · 0 5. C 2 7 Η 3 7 Ν 9 〇4 S; 0 · 50 0 Η 2 〇 Computation 消费 Printed by the Consumer Cooperative of the Central Standards Bureau of the Ministry of Economic Affairs 2 2 2 3 4 t—- 3HHHHHHH 713222463. \ rv / {\ r \ 4D5040422 5C1804510 2 Ν 6 4 6 Η m Η 6 / (\ ο 〇 \) y \) / Ν) / \ iy \ j, mmqmms% 7 2 (Please read the precautions on the back first (Fill in this page)

本纸張尺度適用中國國家標準（CNS ) A4規格（210X 297公釐） -122 - 524805 kl B7 五、發明説明（12〇) 4 · 2 5 ( 2 Η，t )， 5 · 7 2 ( 2 Η，s )， 7 · 1 3 ( 1 Η，d )， 7 · 8 3 ( 1 Η，d )， 7 · 8 5 ( 1 Η，s )， 8 . 7 4 ( 1 Η，s )， 1 Ο · 6 2 ( 1 Η，s ) ° LRMS:m/z 584(Μ+1)+。 實施例7 9 5 — {5 —〔4 一（2 —甲氧乙基）六氫吡畊一1 — 基磺醯基〕一 2 —正丙氧苯基〕一 2 -（1—甲基—1， 2，4 一三唑—5 —基）甲基—3 —正丙基—2，6 —二 氫一 7Η —吡唑並〔4，3 — d〕嘧啶一 7 —酮 由製備例6 0之標題化合物及1 一（ 2 —甲氧乙基） 六氫吡畊依實施例1之步驟製得，呈白色固體（8 9 % ) 〇 經濟部中央標準局員工消費合作社印製 (請先閲讀背面之注意事項再填寫本頁) 元素分析實測値：c，5 4 · 3 6 ; Η，6 · 3 8 ; N， 2〇.15°C38H39N9〇5S計算値 C，54.80;H，6.41;N，2〇.54%。 5 ( C D C 1 3 ) :l.〇〇（3H，t)， 1 · 1 7 ( 3 H，t )， 1 · 8 0 ( 2 H，m )， 2 ·〇 4 ( 2 H ，m )， 本紙張尺度適用中國國家標準（CNS ) A4規格（210X 297公釐） -123 - 524805 ΑΊ B7 五、發明説明（121) 2 · 5 8 ( 6 Η，m )， 3 · 1 〇（4 Η，m )， 3 · 3 〇（3 Η，s )， 3 · 4 3 ( 2 Η，t )， 4 · 0 〇（3 Η，s )， 4.26(2H，t)， 5 . 7 2 ( 2 H > s )， 7 . 1 4 ( 1 H，d )， 7 · 8 3 ( 2 H，m )， 8 · 7 7 ( 1 H，s )， l〇.63(lH，s)° L R M S ： m / z 614(M+1)+。 實施例8〇 經濟部中央標準局員工消費合作社印製 (請先閲讀背面之注意事項再填寫本頁) 5 —〔5 —（4 —乙基六氫吼啡一 1 一基礦釀基）一 2 —正丙氧苯基〕一2 — (1— (2 —甲氧乙基）一1， 2，4 一三唑一5 —基）甲基—3 —正丙基一 2，6 —二 氫一 7H —吡唑並〔4，3 — d〕嘧啶—7 —酮 由製備例6 5之標題化合物及1 -乙基六氫吡畊依實 施例1之步驟製得，呈白色泡沬狀（6 8 % )。 元素分析實測値：C，5 4 · 9 6 ; Η，6 · 5 9 ; N， 19.67°C29H41N9〇5S 計算値 C，55.49;H，6.58;N，20.08。 5 ( C D C 1 3 ) :l.〇0(6H，m)， 本紙張尺度適用中國國家標準（CNS ) A4規格（210X 297公釐） _ 524805 A7 B7 經濟部中央標準局員工消費合作社印製 五、發明説明（122) 1 . 1 4 ( 3 Η，t )， 1 · 8 Ο ( 2 Η，m )， 1 · 9 8 ( 2 Η，m )， 2 · 3 7 ( 2 Η，Q )， 2 · 5 Ο ( 4 Η，m )， 3 .〇 5 ( 6 Η，m )， 3 · 2 6 ( 3 Η，s )， 3 · 6 8 ( 2 Η，t )， 4 · 2 ◦ ( 2 Η，t )， 4 · 5 8 ( 2 Η，t )， 5 · 7 3 ( 2 Η，s )， 7 · 1 Ο ( 1 Η，d )， 7 · 8 Ο ( 2 Η，m )， 8 · 7 3 ( 1 Η，s )， 10.54(lH，s)。 LRMS :m/z 628 (M+l)+。 實施例8 1 5 —〔 5 — (4 —甲基六氫吼哄一 1 一基擴醯基）一 2 —正丙氧苯基〕一2 — (3_甲基—1 ，2，4 一二口坐 一 5 —基）甲基一 3 —正丙基—2，6 —二氫一7Η —吡 唑並〔4，3 — d〕嘧啶—7 -酮 由製備例7 2之標題化合物及1 -甲基六氫吡畊依實 施例1之步驟製得，呈白色固體（4 9 % )。 (請先閲讀背面之注意事項再填寫本頁) ΦThis paper size applies Chinese National Standard (CNS) A4 specification (210X 297 mm) -122-524805 kl B7 V. Description of the invention (12〇) 4 · 2 5 (2 Η, t), 5 · 7 2 (2 Η, s), 7 · 1 3 (1 Η, d), 7 · 8 3 (1 Η, d), 7 · 8 5 (1 Η, s), 8. 7 4 (1 Η, s), 1 Ο · 6 2 (1 Η, s) ° LRMS: m / z 584 (Μ + 1) +. Example 7 9 5 — {5 — [4-((2-methoxyethyl) hexahydropyridine-1—sulfosulfanyl] —2—n-propoxyphenyl]] 2— (1-methyl— 1,2,4-triazol-5-yl) methyl-3-n-propyl-2,6-dihydro-7 一 -pyrazolo [4,3-d] pyrimidin-7-one Preparation Example 6 The title compound of 0 and 1- (2-methoxyethyl) hexahydropyridine were prepared according to the procedure of Example 1 as a white solid (89%). ○ Printed by the Consumer Cooperative of the Central Standards Bureau of the Ministry of Economic Affairs (please first Read the notes on the reverse side and fill in this page) Elemental analysis: 値: c, 5 4 · 3 6; Η, 6 · 3 8; N, 20.15 ° C38H39N9505S Calculate 値 C, 54.80; H, 6.41; N, 20.54%. 5 (CDC 1 3): 1.0 (3H, t), 1 · 7 (3 H, t), 1 · 8 0 (2 H, m), 2 · 4 (2 H, m), This paper size applies to China National Standard (CNS) A4 (210X 297 mm) -123-524805 ΑΊ B7 V. Description of the invention (121) 2 · 5 8 (6 Η, m), 3 · 1 〇 (4 Η, m), 3 · 3 〇 (3 Η, s), 3 · 4 3 (2 Η, t), 4 · 0 〇 (3 Η, s), 4.26 (2H, t), 5.7 2 (2 H > s), 7. 1 4 (1 H, d), 7 · 8 3 (2 H, m), 8 · 7 7 (1 H, s), 10.63 (lH, s) ° LRMS: m / z 614 (M + 1) +. Example 80: Printed by the Consumer Cooperative of the Central Bureau of Standards of the Ministry of Economic Affairs (please read the precautions on the back before filling this page) 5 — [5 — (4 —Ethylhexahydroorphine — 1 base mineral base) — 2-n-propoxyphenyl]-2- (1- (2-methoxyethyl) -1,2,4-triazole-5-yl) methyl-3-n-propyl-2,6-di Hydrogen-7H-pyrazolo [4,3-d] pyrimidin-7-one was prepared from the title compound of Preparation 65 and 1-ethylhexahydropyridine according to the procedure of Example 1, and showed a white foam. (68%). Elemental analysis: 値: C, 5 4 · 9 6; Η, 6 · 5 9; N, 19.67 ° C 29H41N9O5S Calculate 値 C, 55.49; H, 6.58; N, 20.08. 5 (CDC 1 3): 1.00 (6H, m), this paper size is applicable to Chinese National Standard (CNS) A4 (210X 297 mm) _ 524805 A7 B7 Description of the invention (122) 1. 14 (3 Η, t), 1 · 8 Ο (2 Η, m), 1 · 9 8 (2 Η, m), 2 · 3 7 (2 Η, Q), 2 · 5 Ο (4 Η, m), 3.05 (6 Η, m), 3 · 2 6 (3 Η, s), 3 · 6 8 (2 Η, t), 4 · 2 ◦ (2 Η, t), 4 · 5 8 (2 Η, t), 5 · 7 3 (2 Η, s), 7 · 1 Ο (1 Η, d), 7 · 8 Ο (2 Η, m), 8 · 7 3 (1 Η, s), 10.54 (lH, s). LRMS: m / z 628 (M + l) +. Example 8 1 5 — [5 — (4-methylhexahydrozine—1 1-based fluorenyl) —2—n-propoxyphenyl] —2— (3-methyl-1, 2, 4, 1 Two-positioned one 5-yl) methyl one 3-n-propyl-2,6-dihydro-7-pyrido [4,3-d] pyrimidin-7-one was prepared from the title compound of Preparation 7 2 and 1-Methylhexahydropyridine was prepared according to the procedure of Example 1 as a white solid (49%). (Please read the notes on the back before filling this page) Φ

、1T ΙΦ! 本紙張尺度適用中國國家標準（CNS ) Α4規格（210Χ297公釐）-125 - 524805 kl B7 五、發明説明（123) 5(CDCl3):l.〇2(3H，t)， 1 · 1 5 ( 3 Η，t )， 1 · 8 6 ( 2 Η，m )， 2 . 0 2 ( 2 Η，m )， 2 · 2 7 ( 3 Η，s )， 2 · 4 2 ( 3 Η，s )， 3 · 0 8 ( 4 Η，m )， 4 · 2 4 ( 2 Η，t )， 5 · 6 1 ( 2 Η，s )， 7 · 1 2 ( 1 Η，d )， 7 · 7 9 ( 1 Η，d )， 8 · 7 6 ( 1 Η，s )， 1 0 · 6 5 ( 1 Η，s )。 LRMS:m/z 570 (M+1)+。· 實施例8 2 經濟部中央標準局員工消費合作社印製 (請先閲讀背面之注意事項再填寫本頁) 5 —〔2 —乙氧一5 —（4 一甲基六氫吡畊一 1 一基 磺醯基）苯基〕—2 —（5 —甲基—1，2，4 一噚二唑 —3 —基）甲基一3 —正丙基—2，6 —二氫—7H —吡 口坐並〔4，3 - d〕喷n定—7 -酮 由製備例7 9之標題化合物及1 -甲基六氫吡畊依實 施例1之步驟製得，呈白色固體（47%)。 元素分析實測値·· C，5 2 · 4 4 ; Η，5 · 6 3 ; N， 19 · 48 。C25H32N8〇5S ; H2〇計算値 本紙ifc尺度適用中國國家標準（CNS ) A4規格（210X 297公釐） 「126 - 524805 A7 B7 五、發明説明（124) C，52.25;H，5.96;N，19.5 0%。 (5 ( D M S 0 d 6 ) :0.93 (3H，t)， 1 · 3 4 ( 3 Η，t )， 1 · 7 4 ( 2 Η，m )， 2 · 1 2 ( 3 Η，s )， 2 · 3 5 ( 4 Η，m )， 2 · 5 6 ( 3 Η，s )， 2 . 9 0 ( 4 Η，m )， 2 . 9 8 ( 2 Η，t )， 4 · 2 〇（2 Η，q )， 5 · 7 6 ( 2 Η，s )， 7 · 3 6 ( 1 Η，d )， 7 · 8 1 ( 1 Η，d )， 7 · 8 5 ( 1 Η，s )， 11.80(lH，s)。 LRMS:m/z 557 (M+1)+。 經濟部中央標準局員工消費合作社印製 (請先閱讀背面之注意事項再填寫本頁) 實施例8 3 5 — {2 —乙氧一 5 —〔4 一（2 —經乙基）六氯口比 口井一 1 一基擴Μ基〕苯基} 一2 -（5 -甲基一 1，2， 4 一噚二唑一 3 —基）甲基一 3 —正丙基—2，6 —二氫 —7Η -吡唑並〔4，3 — d〕嘧啶一 7 —酮 由製備例79之標題化合物及1一（2—羥乙基）六 氫吡畊依實施例1之步驟製得，呈固體（5 6 % )。 本纸張尺度適用中國國家標準（CNS ) A4規格（210X 297公釐）-127 - 524805 hi B7 五、發明説明（125) 元素分析實測値：c，5 3 · 1 5 ; Η，6 · 1 4 ; N， 17.98°C26H34N8〇6S 計算値 C，53.23;H，5.84;N，19.1〇％。 5(CDCl3):l.〇3(3H，t)， 1 · 6 3 ( 3 H，t )， 1 · 8 8 ( 4 H，m )， 2 · 5 7 ( 4 H，m )， 2 · 6 5 ( 4 H，m )， 3 · 0 5 ( 2 H，t )， 3 · 1 2 ( 4 H，m )， 3 · 6 0 ( 2 H，t )， 4 · 3 8 ( 2 H，Q )， 5 · 6 2 ( 2 H，s )， 7 · 1 6 ( 1 H，d )， 7 · 8 3 ( 1 H，d )， 8 · 7 7 ( 1 H，d )， l〇.61(lH，s)。 經濟部中央標準局員工消費合作社印製 (請先閲讀背面之注意事項再填寫本頁) LRMS:m/z 587 (M+1)+。 實施例8 4 2 —（5 —甲基一1 ，2，4 —哼二唑一3 —基）甲 基一 5 —〔5 — (4 —甲基六氣吼啡一 1 一基礦酿基）— 2 -正丙氧苯基〕一 3 —正丙基—2 ’ 6 — 一氣一 7H — 吡唑並〔4，3 — d〕嘧啶一 7 —酮 本纸張尺度適用中國國家標準（CNS ) A4規格（210X 297公釐）-128 _ 524805 Λ7 B7 五、發明説明（126) 由製備例7 6之標題化合物及1 一甲基六氫吡畊依實 施例1之步驟製得，呈白色固體（9 1 % )。 元素分析實測値：C，5 4 · 4 3 ; Η，6 · ◦ 6 ; N， 19.46°C26H34N8〇5S 計算値 C，54.72 ;H，6.01 ;N，19.64%。 5 ( D M S 0 d 6 ):〇.94(6H，m)， 1 . 7 4 ( 4 H，m )， 2 . 1 5 ( 3 H，s )， 2 · 3 6 ( 4 H，m )， 2.58(3H，s)， 2 · 9 〇（4 H，m )， 2 · 9 8 ( 2 H，t )， 4 · 1 2 ( 2 H，t )， 5 · 7 8 ( 2 H，s )， 7 · 3 8 ( 1 H，d )， 7 · 8 〇（1 H，d )， 7 · 8 4 ( 1 H，s )， 經濟部中央標準局員工消費合作社印製 11.79(lH，s)。 L R M S ： m / z 571(M+1)+。 實施例8 5 5 -〔5— (4 —乙基六氫吼畊一 1 一基礦釀基）一 2 —正丙氧苯基〕一2 — (5 —甲基—1，2，4 —鳄二 唑一 3 —基）甲基一3 —正丙基—2，6 -二氫—7H — -129- (請先閱讀背面之注意事項再填寫本頁) 本紙張尺度適用中國國家標準（CNS ) A4規格（210X 297公釐） 524805 A7 B7 五、發明説明（127) 口比11坐並〔4，3 — d〕嚼π定—7 —酮 由製備例7 6之標題化合物及1 -乙基六氫吡畊依實 施例1之步驟製得，呈白色固體（70)%)。 元素分析實測値：C，5 4 · 8 5 ; Η，6 · 1 6 ; N， 18 · 69 。C27H36N8〇5S ；〇· 25H2〇計算値 C，55.04;H，6.24;N，19.02。 (5 ( C D C 1 3 ):〇.98(6H，m)， 1 ·〇 9 ( 3 H，t )， 1 · 8 3 ( 2 H，m )， 1 · 9 8 (, 2 H，m )， 2 · 3 7 ( 2 H，q )， 2 · 4 9 ( 4 H，m )， 2 · 5 4 ( 3 H，s )， 3 · 0 0 ( 2 H，t )， 3 · 0 4 ( 4 H，m )， 4 · 2 0 ( 2 H，t )， 5 · 5 8 ( 2 H，s )， 經濟部中央標準局員工消費合作社印製 (請先閲讀背面之注意事項再填寫本頁) 7 · 1 0 ( 1 H，d )， 7 · 7 8 ( l.H ， d )， 8 · 7 2 ( 1 H，s ).， l〇.53(lH，s)° L R M S ： m / z 584 (M+1)+。 實施例8 6 本紙張尺度適用中國國家標準（CNS ) A4規格（210X297公釐） -130- 524805 A7 五、發明説明（128) 5 — {5 —〔4 一（2 —羥乙基）六氫吡畊一 1 一基 磺醯基〕—2 -正丙氧苯基} 一2 -（5 —甲基一 1，2 ，4 一鸣二唑一 3 —基）甲基—3 —正丙基一 2，6 —二 氫—7H —吡唑並〔4，3 — d〕嘧啶一 7 —酮 由製備例76之標題化合物及1 一（2 —羥乙基）六 氫吡畊依實施例1之步驟製得，呈白色固體（8 6 % )。 元素分析實測値·· C，5 3 . 2 2 ; Η，6 ·〇0 ; N， 18 · 06。C27H36N8〇6S ; 0 · 25H2〇；0 · 10CH3C〇2CH2CH3 計算値 (請先閱讀背面之注意事項再填寫本頁) 經濟部中央標準局員工消費合作社印製 ο 3HHHHHHHHHHHHH 613221542422211 • c ^' /IV /IV Γν /IV Γν Γν Γν /(V /IV /(V rv /l\ ooDVI 00 CD 00 1± LO CXI nu no oo 00 -4 5C1803560162618， /L · c 5 1122 2233 3 4577 N 2 τ—1 6 Η % 5 2 8 \)y \)yt m m smmtmmtsdd Η 3 /ι\ 4 ο 本纸張尺度適用中國國家標準（CNS ) A4規格（210X 297公釐） -131 - 524805 經濟部中央標準局員工消費合作社印製 A7 B7 五、發明説明（129) 8 · 7 9 ( 1 Η，s )， 1〇.6〇(1H，s)。 L R M S : m / z 600 (M)+。 實施例8 7 2—;基一 5 —〔2 —乙氧一5 — (4 —甲基六氫口比 哄一 1 一基磺醯基）苯基〕—3 -正丙基一 2，6 -二氫 一 7 Η —吡唑並〔4，3 — d〕嘧啶—7 -酮 在氮氣下將三乙胺（64# 1 ，0 · 46 m mo 1) ，甲酸鈉（32mg，〇 · 46mmo 1)及肆（三苯基 膦）鈀（〇) (17mg，〇.〇15mmol)加入由 實施例88標題化合物（200mg，0 . 32mmo 1 )置於乙腈（1 · 5ml)與二甲亞硕（1 · 5ml)之 混合物中所形成的攪拌溶液裡，令整個混合物加熱迴流 2 0小時，然後減壓蒸發。把殘餘物懸浮在鹽水（1〇 m 1 )裡，再以乙酸乙酯（總量3 0 m 1 )對該懸浮液進 行萃取，合倂的萃取液經乾燥（N a 2 S 0 4 )後減壓蒸發 ’接著以管柱層析法利用乙酸乙酯：甲醇：0 · 8 8 0氨 水（9 4 : 5 : 1 )爲沖提液在矽膠上純化殘餘物而得到 無色膠狀（gum )的標題化合物（8 4 m g )。 5(CDCl3):〇.95(3H，t)， 1 · 6 2 ( 3 Η，t )， 1 · 7 4 ( 2 Η，m )， 2 · 3 0 ( 3 Η，s )， 本紙張尺度適用中國國家標準（CNS ) Α4規格（21〇Χ 297公釐）_ 132 - (請先閱讀背面之注意事項再填寫本頁)、 1T ΙΦ! This paper size applies to Chinese National Standard (CNS) A4 specification (210 × 297 mm) -125-524805 kl B7 V. Description of the invention (123) 5 (CDCl3): 1.02 (3H, t), 1 · 1 5 (3 Η, t), 1 · 8 6 (2 Η, m), 2. 0 2 (2 Η, m), 2 · 2 7 (3 Η, s), 2 · 4 2 (3 Η , S), 3 · 0 8 (4 Η, m), 4 · 2 4 (2 Η, t), 5 · 6 1 (2 Η, s), 7 · 1 2 (1 Η, d), 7 · 7 9 (1 Η, d), 8 · 7 6 (1 Η, s), 1 0 · 6 5 (1 Η, s). LRMS: m / z 570 (M + 1) +. · Example 8 2 Printed by the Consumer Cooperatives of the Central Standards Bureau of the Ministry of Economic Affairs (please read the precautions on the back before filling out this page) 5 — [2 —Ethoxyl 5 — (4 Methylpyridine 1 1 1 Sulfofluorenyl) phenyl] -2 — (5-methyl-1,2,4-dioxadiazol-3-yl) methyl-1-n-propyl-2,6-dihydro-7H —pyridine Mouth sitting and [4,3-d] spray n--7-one was prepared from the title compound of Preparation Example 7 9 and 1-methylhexahydropyridine according to the procedure of Example 1 as a white solid (47%) . Elemental analysis: 値 ·· C, 5 2 · 4 4; Η, 5 · 6 3; N, 19 · 48. C25H32N8〇5S; H2〇 Calculate the paper ifc standard applicable to Chinese National Standard (CNS) A4 specification (210X 297 mm) "126-524805 A7 B7 V. Description of the invention (124) C, 52.25; H, 5.96; N, 19.5 0%. (5 (DMS 0 d 6): 0.93 (3H, t), 1 · 3 4 (3 Η, t), 1 · 7 4 (2 Η, m), 2 · 1 2 (3 Η, s ), 2 · 3 5 (4 Η, m), 2 · 5 6 (3 Η, m), 2. 9 0 (4 Η, m), 2. 9 8 (2 Η, t), 4 · 2 〇 (2 Η, q), 5 · 7 6 (2 Η, s), 7 · 3 6 (1 Η, d), 7 · 8 1 (1 Η, d), 7 · 8 5 (1 Η, s) , 11.80 (lH, s). LRMS: m / z 557 (M + 1) +. Printed by the Consumer Cooperative of the Central Standards Bureau of the Ministry of Economic Affairs (please read the precautions on the back before filling this page). Example 8 3 5 — {2 —Ethoxyl 5 — [4 1 (2—Ethyl) hexachloride than Mouth 1—1 1-Methyl] phenyl] 1 2— (5-methyl-1, 2, 4— Oxadiazol-3-yl) methyl-1 3-n-propyl-2,6-dihydro-7H-pyrazolo [4,3-d] pyrimidin-7-one from the title compound of Preparation 79 and 1 One (2-hydroxyethyl Hexahydropyridine was prepared in accordance with the procedure of Example 1 and was solid (56%). This paper size applies the Chinese National Standard (CNS) A4 specification (210X 297 mm) -127-524805 hi B7 V. Description of the invention (125) Measured 値 by elemental analysis: c, 5 3 · 15; Η, 6 · 1 4; N, 17.98 ° C 26H34N8〇6S Calculate 値 C, 53.23; H, 5.84; N, 19.10%. 5 (CDCl3) : 1.03 (3H, t), 1 · 6 3 (3 H, t), 1 · 8 8 (4 H, m), 2 · 5 7 (4 H, m), 2 · 6 5 (4 H, m), 3 · 0 5 (2 H, t), 3 · 1 2 (4 H, m), 3 · 6 0 (2 H, t), 4 · 3 8 (2 H, Q), 5 · 6 2 (2 H, s), 7 · 16 (1 H, d), 7 · 8 3 (1 H, d), 8 · 7 7 (1 H, d), 10.61 (1H, s). Printed by the Employees' Cooperatives of the Central Bureau of Standards of the Ministry of Economic Affairs (please read the notes on the back before filling out this page) LRMS: m / z 587 (M + 1) +. Example 8 4 2 — (5-methyl-1, 2, 4, 4-humidazol-3-yl) methyl-5 — [5 — (4-methylhexazine-1 — 1-based mineral base) ) — 2 -n-propoxyphenyl]-3-n-propyl-2 '6-monogas-7H-pyrazolo [4,3-d] pyrimidine-7-ketone The paper size applies to Chinese national standards (CNS ) A4 specification (210X 297 mm) -128 _ 524805 Λ7 B7 V. Description of the invention (126) Prepared from the title compound of Preparation Example 7 6 and 1-methylhexahydropyridine according to the procedure of Example 1, white Solid (91%). Elemental analysis: 値: C, 5 4 · 4 3; Η, 6 · ◦ 6; N, 19.46 ° C 26H34N8005S Calculate 値 C, 54.72; H, 6.01; N, 19.64%. 5 (DMS 0 d 6): 0.94 (6H, m), 1. 7 4 (4 H, m), 2. 1 5 (3 H, s), 2 · 3 6 (4 H, m), 2.58 (3H, s), 2 · 9〇 (4 H, m), 2 · 9 8 (2 H, t), 4 · 1 2 (2 H, t), 5 · 7 8 (2 H, s) , 7 · 3 8 (1 H, d), 7 · 8 〇 (1 H, d), 7 · 8 4 (1 H, s), 11.79 (lH, s) printed by the Consumer Cooperative of the Central Standards Bureau of the Ministry of Economic Affairs . L R M S: m / z 571 (M + 1) +. Example 8 5 5-[5 -— (4-Ethyl hexahydrocarbyl-1, 1-based mineral base)-2—n-propoxyphenyl] —2— (5-methyl-1, 2, 4— Crocodiazole- 3 -yl) methyl- 3 -n-propyl-2,6 -dihydro-7H — -129- (Please read the precautions on the back before filling this page) This paper size applies to Chinese national standards ( CNS) A4 specification (210X 297 mm) 524805 A7 B7 V. Description of the invention (127) Mouth ratio of 11 and [4,3 — d] π-D7-7 —one from the title compound of Preparation Example 7 6 and 1- Ethylhexahydropyridine was prepared according to the procedure of Example 1 as a white solid (70)%). Elemental analysis: 値: C, 5 4 · 8 5; Η, 6 · 16; N, 18 · 69. C27H36N8005S; 0.25H20 calculated C, 55.04; H, 6.24; N, 19.02. (5 (CDC 1 3): 0.98 (6H, m), 1.09 (3H, t), 1.83 (2H, m), 1.98 (2H, m) , 2 · 3 7 (2 H, q), 2 · 4 9 (4 H, m), 2 · 5 4 (3 H, s), 3 · 0 0 (2 H, t), 3 · 0 4 ( 4 H, m), 4 · 2 0 (2 H, t), 5 · 5 8 (2 H, s), printed by the Consumer Cooperatives of the Central Standards Bureau of the Ministry of Economic Affairs (please read the precautions on the back before filling this page) ) 7 · 1 0 (1 H, d), 7 · 7 8 (1H, d), 8 · 7 2 (1 H, s)., 10.53 (lH, s) ° LRMS: m / z 584 (M + 1) +. Example 8 6 This paper size applies Chinese National Standard (CNS) A4 specification (210X297 mm) -130- 524805 A7 V. Description of the invention (128) 5 — {5 — [4 1 (2 —Hydroxyethyl) hexahydropyridine-1 1-sulfosulfanyl] -2-n-propoxyphenyl} 2— (5-methyl-1,2,4-imidazol-3-yl) formyl Propyl-3-n-propyl-2,6-dihydro-7H-pyrazolo [4,3-d] pyrimidin-7-one was prepared from the title compound of Preparation 76 and 1- (2-hydroxyethyl) hexa Hydropyrine was prepared according to the procedure of Example 1, White solid (86%). Elemental analysis measured 値 ·· C, 5 3. 2 2; Η, 6 · 〇0; N, 18 · 06. C27H36N8〇6S; 0 · 25H2〇; 0 · 10CH3C〇2CH2CH3 calculation値 (Please read the notes on the back before filling out this page) Printed by the Consumer Cooperatives of the Central Standards Bureau of the Ministry of Economic Affairs 3HHHHHHHHHHHHHH 613221542422211 • c ^ '/ IV / IV Γν / IV Γν Γν Γν / (V / IV / (V rv / l \ ooDVI 00 CD 00 1 ± LO CXI nu no oo 00 -4 5C1803560162618, / L · c 5 1122 2233 3 4577 N 2 τ—1 6 Η% 5 2 8 \) y \) yt mm smmtmmtsdd Η 3 / ι \ 4 ο This paper size applies to Chinese National Standard (CNS) A4 (210X 297 mm) -131-524805 Printed by A7 B7, Consumer Cooperative of the Central Standards Bureau of the Ministry of Economic Affairs 5. Description of the invention (129) 8 · 7 9 (1 H, s), 10.6 (1 H, s). L R M S: m / z 600 (M) +. Example 8 7 2—; radicals 5— [2-ethoxy-5— (4-methylhexahydrofluoride 1—1-sulfofluorenyl) phenyl] 3—n-propyl-2, 6 -Dihydro-7 pyrene-pyrazolo [4,3-d] pyrimidin-7-one under nitrogen with triethylamine (64 # 1, 0.46 m mo 1), sodium formate (32 mg, 0.46 mmo 1 ) And (triphenylphosphine) palladium (0) (17 mg, 0.015 mmol) were added from the title compound of Example 88 (200 mg, 0.32 mmo 1) in acetonitrile (1.5 ml) and dimethyl asus ( In a stirred solution formed in a mixture of 1.5 ml), the entire mixture was heated under reflux for 20 hours, and then evaporated under reduced pressure. The residue was suspended in brine (10 m 1), and the suspension was extracted with ethyl acetate (a total of 30 m 1). The combined extract was dried (N a 2 S 0 4) Evaporate under reduced pressure, and then use column chromatography to purify the residue on silica gel using ethyl acetate: methanol: 0.888 ammonia (9 4: 5: 1) as the eluent to obtain a colorless gum (gum). The title compound (84 mg). 5 (CDCl3): 0.95 (3H, t), 1.62 (3 Η, t), 1 · 7 4 (2 Η, m), 2 · 3 0 (3 Η, s), paper size Applicable to China National Standard (CNS) Α4 specification (21〇 × 297 mm) _ 132-(Please read the precautions on the back before filling this page)

、1T 4, 524805 ΑΊ 五、發明説明（13〇) 2 · 5 7 ( 4 Η，m )， 2.9〇（2H，t)， 3 · 1 6 ( 4 Η，m )， 4 · 3 9 ( 2 Η，Q )， 5 · 5 8 ( 2 Η，s )， 7·1〇 — 7.36(6H，m)， 7 · 8 2 ( 1 Η，d )， 8 · 7 8 ( 1 Η，s )， l〇.60(lH，s) ， 〇 L R M S ： m / z 551(M+1)+。 實施例8 8 2— (4 —溴苄基）—5 —〔2 —乙氧一5 — (4 — 甲基六氫吡啡一 1 一基磺醯基）苯基〕一 3 -正丙基一 2 ，6 —二氫—7H —吡唑並〔4，3 - d〕嘧啶—7 —酮 由製備例8 9之標題化合物及1 -甲基六氫吡畊依實 施例1之步驟製得，呈白色泡沬狀（5 7 % )。 經濟部中央標準局員工消費合作社印製 (請先閱讀背面之注意事項再填寫本頁) 元素分析實測値：C，5 2 · 8 0 ; Η，5 · 3 8 ; N， 1 2 · 83 °C28H33BrN6〇4S ; Ο · 5〇Η2〇計 算値C，52.64;H，5.37;N，13.16% ο (5 ( C D C 1 3 ) :0.93(3H，t)， 1 · 6 0 ( 3 H，t )， 1 · 7 2 ( 2 H，m )， 本纸張尺度適用中國國家標準（CNS ) A4規格（210X 297公釐） _ 133 524805 Λ7 B7 五、發明説明（131) 2 · 4 〇（3 Η，s )， 2 · 6 4 ( 4 Η，m )， 2 · 9 Ο ( 2 Η，t )， 3 · 2 2 ( 4 Η，m )， 4 · 3 8 ( 2 Η，Q )， 5 · 4 8 ( 2 Η，s )， 7·〇4(2Η，〇， * 7 · 1 4 ( 1 Η，d )， 7 · 4 4 ( 2 Η，d )， 7 · 8 〇（1 Η，d )， 8 · 7 6 ( 1 Η，s )， l〇.62(lH，s)° 實施例8 9 2 — (4 —溴苄基）—5 — {2 —乙氧一5 —〔4 — 經濟部中央標準局員工消費合作社印製 (請先閱讀背面之注意事項再填寫本頁) (2 -經乙基）六氧吼哄一 1 一基磺醯基〕苯基} 一 3 -正丙基—2，6 —二氫一 7H_吡唑並〔4，3 — d〕嘧 υ定—7 -醒 由製備例8 9之標題化合物及1 — ( 2 -羥乙基）六 氫吡啡依實施例1之步驟製得，呈白色泡沬狀（6 6 % ) 〇 元素分析實測値：c，5 2 · 1 3 ; Η，5 · 3 7 ; N， 1 2 · 42 。C29H35BrN6〇5S ; 〇 · 5〇112〇計 算値C，52.05;H，5.43; ， 12.57%。 本紙張尺度適用中國國家標準（CNS ) A4規格（210X 297公釐） -1 34 - 524805 Λ7 B7 五、發明説明（132) δ ( C D C 1 3 ) :0.97(3H，t)， 1 · 6 3 ( 3 Η，t )， 1 · 7 6 ( 2 Η，m )， 2 · 6 8 ( 3 Η，m )， 2 · 7 8 ( 4 Η，m )， 2 · 8 6 ( 2 Η，t )， 3 · 2 〇（4 Η，m )， 3 · 6 6 ( 2 Η，m )， 4 · 3 9 ( 2 Η，q )， 5 · 5 〇（2 Η，s )， 7 · 1 Ο ( 2 Η，d )， 7 · 1 8 ( 1 Η，d )， 7 · 4 6 ( 2 Η，d )， 7 · 8 1 ( 1 Η，d )， 8 · 7 7 ( 1 Η，s )， l〇.64(lH，s)。 LRMS:m/z 659 (M)+。 經濟部中央標準局員工消費合作社印製 (請先閱讀背面之注意事項再填寫本頁) 實施例9 0 2 -（4 一胺羰基苄基）—5 —〔2 —乙氧一5 —( 4 一甲基六氣吼哄一 1 一基磺酸基）苯基〕一 3 —正丙基 —2，6 —二氫—7H —吡唑並〔4，3 - d〕嘧啶一 7 —酮 由製備例9 2之標題化合物及1 -甲基六氫吡畊依實 本纸張尺度適用中國國家標準（CNS ) A4規格（210X 297公釐）-135 - 524805 經濟部中央標準局員工消費合作社印製 Λ7 B7 五、發明説明（133) 施例1之步驟製得，呈白色泡沬狀（2 8 % )。 元素分析實測値：C，5 5 · 7 6 ; Η，6 · 0 4 ; N， 15 · 56 。 C29H35N7〇5S ； 0 . 5 0 C Η 2 C 1 2 計算値 C，55 .78 ;Η，5 .71 ;Ν，15 ·44 %。 5 ( C D C 1 a ):〇.93(3H，t)， 1 · 6 3 ( 3 H，t )， 1 · 7 6 ( 2 H，m )， 2 · 2 4 ( 3 H，s )， 2 · 4 6 ( 4 H，m )， 2 · 9 〇（2 H，t )， 3 · 0 8 ( 4 H，m )， 4 · 3 8 ( 2 H，Q )， 5 · 5 9 ( 2 H，s )， 7 · 1 7 ( 1 H，d )， 7 · 2 5 ( 3 H，m )， 7 · 8 0 ( 3 H，m )， 8 · 7 8 ( 1 H，s )， 10.69(lH，s)° LRMS:m/z 594(M+1)+。 實施例9 1 5 —〔2 —乙氧一5 — (4 —甲基六比哄一1—基 磺醯基）苯基〕—2 -（4 一硝苄基）一 3 -正丙基一 2 (請先閲讀背面之注意事項再填寫本頁)1T 4, 524805 ΑΊ V. Description of the invention (13〇) 2 · 5 7 (4 Η, m), 2.9〇 (2H, t), 3 · 1 6 (4 Η, m), 4 · 3 9 (2 Η, Q), 5 · 5 8 (2 Η, s), 7. · 10— 7.36 (6H, m), 7 · 8 2 (1 Η, d), 8 · 7 8 (1 Η, s), 10.60 (1H, s), 0 LRMS: m / z 551 (M + 1) +. Example 8 8 2— (4-Bromobenzyl) -5— [2—Ethoxy-5— (4-methylhexahydropyridine-1—1-sulfofluorenyl) phenyl] —3-n-propyl A 2,6-dihydro-7H-pyrazolo [4,3-d] pyrimidin-7-one was prepared from the title compound of Preparation Example 8-9 and 1-methylhexahydropyridine according to the procedure of Example 1. , A white bubble-like shape (57%). Printed by the Consumer Cooperatives of the Central Standards Bureau of the Ministry of Economic Affairs (please read the precautions on the back before filling in this page) Elemental analysis and measurement 値: C, 5 2 · 8 0; Η, 5 · 3 8; N, 1 2 · 83 ° C28H33BrN6〇4S; Calculate 値 C, 52.64; H, 5.37; N, 13.16% ο (5 (CDC 1 3): 0.93 (3H, t), 1.60 (3 H, t) , 1 · 7 2 (2 H, m), this paper size applies to Chinese National Standard (CNS) A4 specification (210X 297 mm) _ 133 524805 Λ7 B7 V. Description of the invention (131) 2 · 4 〇 (3 Η , S), 2 · 6 4 (4 Η, m), 2 · 9 Ο (2 Η, t), 3 · 2 2 (4 Η, m), 4 · 3 8 (2 Η, Q), 5 · 4 8 (2 Η, s), 7.04 (2 Η, 0, * 7 · 1 4 (1 Η, d), 7 · 4 4 (2 Η, d), 7 · 8 〇 (1 Η, d ), 8 · 7 6 (1 Η, s), 10.62 (lH, s) ° Example 8 9 2 — (4-Bromobenzyl) — 5 — {2 —Ethoxy-5 — [4 — Printed by the Consumer Cooperatives of the Central Bureau of Standards of the Ministry of Economic Affairs (please read the precautions on the back before filling this page) (2-Ethyl) Hexaoxine-1 1-sulfofluorenyl] phenyl} 1- 3- N-propyl-2,6-dihydro-7H_pyrazolo [4,3-d] pyrimidine-7-propionate from the title compound of Preparation Example 9 and 1- (2-hydroxyethyl) hexahydro Pyrophylline was prepared according to the procedure of Example 1 and showed a white foamy shape (66%). 元素 Measured by elemental analysis 値: c, 5 2 · 1 3; Η, 5 · 3 7; N, 1 2 · 42. C29H35BrN6 〇5S; 〇 5〇112〇 Calculate 値 C, 52.05; H, 5.43;, 12.57%. This paper size applies to China National Standard (CNS) A4 specification (210X 297 mm) -1 34-524805 Λ7 B7 V. Description of the invention (132) δ (CDC 1 3): 0.97 (3H, t), 1 · 6 3 (3 Η, t), 1 · 7 6 (2 Η, m), 2 · 6 8 (3 Η, m ), 2 · 7 8 (4 Η, m), 2 · 8 6 (2 Η, t), 3 · 2 0 (4 Η, m), 3 · 6 6 (2 Η, m), 4 · 3 9 (2 Η, q), 5 · 5 〇 (2 Η, s), 7 · 1 〇 (2 Η, d), 7 · 1 8 (1 Η, d), 7 · 4 6 (2 Η, d) , 7 · 8 1 (1Η, d), 8 · 7 7 (1Η, s), 10.64 (1H, s). LRMS: m / z 659 (M) +. Printed by the Consumer Cooperative of the Central Bureau of Standards of the Ministry of Economic Affairs (please read the precautions on the back before filling this page) Example 9 0 2-(4 Monoaminocarbonylbenzyl) — 5 — [2 —Ethoxyl 5 — (4 Monomethylhexazine-coated 1-monosulfonyl) phenyl] -3-n-propyl-2,6-dihydro-7H-pyrazolo [4,3-d] pyrimidin-7-one Preparation Example 9 The title compound of 2 and 1-methylhexahydropyridine according to the paper size Applicable to the Chinese National Standard (CNS) A4 specification (210X 297 mm) -135-524805 Printed by the Consumers Cooperative of the Central Standards Bureau of the Ministry of Economic Affairs Preparation Λ7 B7 V. Description of the invention (133) It was prepared by the procedure of Example 1 and was white foamy (28%). Elemental analysis: 値: C, 5 5 · 7 6; Η, 6 · 0 4; N, 15 · 56. C29H35N7〇5S; 0.50 C Η 2 C 1 2 Calculate 値 C, 55.78; Η, 5.71; N, 15.44%. 5 (CDC 1 a): 0.93 (3H, t), 1. 6 3 (3 H, t), 1 · 7 6 (2 H, m), 2 · 2 4 (3 H, s), 2 · 4 6 (4 H, m), 2 · 9 〇 (2 H, t), 3 · 0 8 (4 H, m), 4 · 3 8 (2 H, Q), 5 · 5 9 (2 H , S), 7 · 1 7 (1 H, d), 7 · 2 5 (3 H, m), 7 · 8 0 (3 H, m), 8 · 7 8 (1 H, s), 10.69 ( lH, s) ° LRMS: m / z 594 (M + 1) +. Example 9 1 5 — [2-Ethoxy-5— (4-methylhexabiol—1-sulfofluorenyl) phenyl] -2— (4-nitrobenzyl) —3-n-propyl— 2 (Please read the notes on the back before filling this page)

本紙張尺度適用中國國家標準（CNS ) A4規格（210X297公釐） -136- 524805 • μ Β7 五、發明説明（134)，6 -二氫一 7Η —吡唑並〔4，3 - d〕嘧啶一 7 —酮 由製備例9 6之標題化合物及1 -甲基六氫吡畊依實 施例1之步驟製得，呈黃色泡線狀（8 2 % )。元素分析實測値：C，5 5 · 9 6 ; Η，5 · 5 4 ; N， 16.27°C28H33N7〇6S 計算値 經濟部中央標準局員工消費合作社印製The size of this paper is applicable to Chinese National Standard (CNS) A4 (210X297 mm) -136- 524805 • μ Β7 V. Description of the invention (134), 6-dihydro-7Η —pyrazolo [4,3-d] pyrimidine A 7-one was prepared from the title compound of Preparation Example 96 and 1-methylhexahydropyridine according to the procedure of Example 1, and was yellow-foamed (82%). Elemental analysis: ，: C, 5 5 · 9 6; Η, 5 · 5 4; N, 16.27 ° C28H33N7〇6S calculation 印 Printed by the Consumer Cooperative of the Central Standards Bureau of the Ministry of Economic Affairs

6 3HHHHHHHHHHHHHH1/ 4132342422121221( m • /(V SV /IV rv /(V /IV /' /(V /IV /IV /V /(\ /—-' /IV 00 · · 6D547700844520886S 5C67249136138277 M Ϊ/—V·············. (u C0O1122234577 78881L N 8 5 5 Η Η 3 /V4 9ο ms m tmQ s d d d d d s % 64 6 (請先閱讀背面之注意事項再填寫本頁) Η z s +Μ /IV 6 9 5 本紙張尺度適用中國國家標準（CNS ) A4規格（210X 297公釐）-137 - 524805 A7 B7 五、發明説明（135) 實施例9 2 5 — {2 —乙氧一5 —〔4 — (2 —羥乙基）六氫吡 畊—1 一基磺醯基〕苯基} 一 2 -（4 一硝苄基）一 3 -正丙基一 2，6 —之二氫一 7H -吡唑並〔4，3 — d〕 嘧啶—7 -酮 由製備例9 6之標題化合物及1 一（ 2 —羥乙基）六 氫吡哄依實施例1之步驟製得，呈黃色油狀物（9 0 % ) 〇 元素分析實測値：C，5 4 · 8 3 ; Η，5 · 6 1 ; N， 15 · 46 。C29H35N7〇7S ;〇· 5〇H2〇計算値 C，54.88;H，5.72;N，15.45%。 (5 ( C D C 1 a ) :0.96(3H，t)， 1 · 6 2 ( 3 H，t )， 1 · 7 4 ( 2 H，m )， 2 · 3 0 ( 1 H，s )， 2 · 5 5 ( 2 H，t )， 2 . 6 0 ( 4 H，m )， 經濟部中央標準局員工消費合作社印製 (請先閲讀背面之注意事項再填寫本頁) 2 · 9 0 ( 2 H，t )， 3 · 1 0 ( 4 H，m )， 3 · 5 8 ( 2 H，m )， 4 · 3 9 ( 2 H，q )， 5 · 6 4 ( 2 H，s )， 7 · 1 7 ( 1 H，d )， 7 · 3 3 ( 2 H，d )， 本纸張尺度適用中國國家標準（CMS ) A4規格（210X 297公釐） -138 - 524805 A7 B7 五、發明説明（136) 7 · 8 2 ( 1 Η，d )， 8.20(2H，d)， 8 · 7 8 ( 1 Η，s )， 10.70(lH，s)。 實施例9 3 2 — (4 —胺苄基）一5 —〔2 —乙氧一5 — (4 — 甲基六氨吼啡一 1 一基擴酸基）苯基〕一 3 -正丙基一 2 ，6 —二氫—7H —吡唑並〔4，3 — d〕嘧啶—7 -酮 由實施例9 1之標題化合物依實施例5 2之步驟製得 ，呈白色泡沬狀（77%)。 元素分析實測値：C，5 8 · 5 1 ; Η，6 · 1 8 ; N， 16 · 76 。C28H35N7〇4S ; 0 · 50H2〇計算値 C，58.52; Η，6·31;Ν，17.06%。 δ ( C D C 1 a ) :0.83 (3H，t) ， 1 · 6 4 ( 3 H，t )， 1 · 7 2 ( 2 H，m )， 經濟部中央標準局員工消費合作社印製 (請先閱讀背面之注意事項再填寫本頁) 2 · 2 7 ( 3 H，s )， 2 · 4 8 ( 4 H，m )， 2 · 9 0 ( 2 H，t )， 3 · 1 0 ( 4 H，m )， 3 · 6 9 ( 2 H，s )， 4 . 3 6 ( 2 H ^ q )， 5 · 4 3 ( 2 H，s )， 本紙張尺度適用中國國家標準（CNS ) A4規格（210X297公釐） -139 - 524805 Λ7 B7 五、發明説明（137) 6 · 6 2 ( 2 Η，d )， 7 ·〇 6 ( 2 Η，d )， 7 · 1 4 ( 1 Η，d )， 7 · 8 〇（1 Η，d )， 8 · 7 6 ( 1 Η，s )， l〇.58(lH，s)ppm。 實施例9 4 1一（N —乙基胺羰甲基）一5 —〔5 — (4 —甲基 六氨吼哄一 1 一基礦薩基）一 2 -正丙氧苯基〕一 3 -正 丙基—1，6 —二氫一 7H —吡唑並〔4，3 — d〕嘧陡 —7 -酮 由製備例1 0 2之標題化合物及1 -甲基六氫吡畊依 實施例1之步驟製得，呈棕色固體（40%)。 5(CDCl3)：l.〇l(3H^t)^ (請先閱讀背面之注意事項再填寫本頁) 經濟部中央標準局員工消費合作社印製 2 2 2 2 3 3 hhhhhhhhh 332234242 rv rv /IV /IV /IV rv rv /l\ /(V 889489709 018024912 nm/ \)y NMy \My N)/ \)y \)/ \)/ ttmmsmtmm 本纸張尺度適用中國國家標準（CNS ) A4規格（210X 297公釐）-140 - 524805 A7 B7 五、發明説明（138) 4 · 2 5 ( 2 Η，t )， 5 · 2 3 ( 2 Η，s )， 6 · 1 4 ( 1 Η，s )， 7 · 1 8 ( 1 Η，d )， 7 · 8 6 ( 1 Η，d )， 8 · 8 7 ( 1 Η，s )， l〇.95(lH，s)。 L R M S ： m / z 56〇（M+1)+。 實施例9 5 1—〔N— (2 —甲氧乙基）胺羰甲基〕一5 —〔5 —(4一甲基六氫吼哄一1一基礦酸基）一2—正丙氧苯 基〕—3 —正丙基—1，6 —二氫—7H —吡唑並〔4， 3 - d〕嘧啶—7 -酮 由製備例1 0 3之標題化合物及1 -甲基六氫吡畊依 依實施例1之步驟製得，呈白色泡沬狀（6 3 % )。 經濟部中央標準局員工消費合作社印製 (請先閱讀背面之注意事項再填寫本頁) 元素分析實測値：C，5 4 · 6 0 ; Η，6 · 8 7 ; N， 16.02°C27H39N7〇6S 計算値 C，54.98;H，6.67;N，16.〇3%。 ά ( C D C 1 3 ) :l.〇5(3H，t)， 1 · 2 0 ( 3 H，t )， 1 . 8 9 ( 2 H，m )， 2 .〇 4 ( 2 H，m )， 2 · 2 9 ( 3 H ， s )， 本紙張尺度適用中國國家標準（CNS ) A4規格（210X 297公釐）-141 - 524805 A7 B7 五、發明説明（139) 2.5〇（4H，m)， 2 · 9 8 ( 2 Η，t )， 3 · 1 〇（4 Η，m )， 3 · 3 3 ( 3 Η，s )， 3 · 4 3 ( 4 Η，m )， 4 · 2 9 ( 2 Η，t )， 5 . 2 8 ( 2 Η，s )， 6 · 4 2 ( 1 Η，s )， 7 · 1 8 ( 1 Η，d )， 7 · 8 6 ( 1 Η，d )， 8 · 8 8 ( 1 Η，s )， l〇.93(lH，s)° L R M S ： m / z 59〇（M+1)+。 實施例9 6 經濟部中央標準局員工消費合作社印製 (請先閱讀背面之注意事項再填寫本頁) 5 —〔5— (4 —甲基六氫吡畊一1 一基磺醯基）一 2 —正丙氧苯基〕—1—(嗎啉一 4 —基羰甲基）一 3 — 正丙基一 1，6 —二氫—7H —吡唑並〔4，3 — d〕嘧 啶一 7 -酮 由製備例1 0 4之標題化合物及1 一甲基六氫吡畊1 依實施例1之步驟製得，呈灰褐色（belge )固體（5 9 % )° 元素分析實測値：C，5 4 · 2 5 ; Η，6 · 5 0 ; N， 14 · 72 。C28H39N7〇6S ; H2〇計算値 本紙張尺度適用中國國家標準（CNS ) A4規格（210X 297公釐）-142 - 524805 經濟部中央標準局員工消費合作社印製 A7 B7 五、發明説明（14〇) C，54.27;H，6.67;N，15.82%。 5(CDCl3):l.〇2(3H，t)， 1 · 1 9 ( 3 Η，t )， 1 · 8 8 ( 2 Η，m )， 2 ·〇 2 ( 2 Η，m >， 2 · 2 7 ( 3 Η，s )， 2 . 5 0 ( 4 Η > m )， 2 · 9 8 ( 2 Η，t )， 3 · 1 2 ( 4 Η，m )，. 3 · 5 6 ( 2 Η，m )， 3 · 6 2 ( 2 Η，m )， 3 · 7 3 ( 4 Η，m )， 4 · 2 4 ( 2 Η，t )， 5 · 4 5 ( 2 Η，.s )， 7 · 1 5 ( 1 Η，d )， 7 · 8 3 ( 1 Η，d )， 8 . 8 6 ( 1 Η，s )， 1 〇· 8 7 ( 1 Η，s )。 LRMS:m/z 6〇2(M+1)+。 實施例9 7 5 —〔5 — (4 —甲基六氫吡畊一 1 一基磺醯基）— 2 -正丙氧苯基〕一 1 一〔 1 S —(嗎啉一4 一基羰基） 乙基〕—3 —正丙基—1，6 —二氫一 7H —吡唑並〔4 本紙張尺度適用中國國家標準（CNS ) A4規格（210X297公釐）-143 - (請先閱讀背面之注意事項再填寫本頁)6 3HHHHHHHHHHHHHHHH1 / 4132342422121221 (m • / (V SV / IV rv / (V / IV / '/ (V / IV / IV / V / (\ / —-' / IV 00 · · 6D547700844520886S 5C67249136138277 M Ϊ / —V · ··········. (U C0O1122234577 78881L N 8 5 5 Η / 3 / V4 9ο ms m tmQ sddddds% 64 6 (Please read the notes on the back before filling this page) Η zs + Μ / IV 6 9 5 This paper size applies Chinese National Standard (CNS) A4 specification (210X 297 mm) -137-524805 A7 B7 V. Description of invention (135) Example 9 2 5 — {2 —Ethoxyl-5 — [4 — (2-Hydroxyethyl) hexahydropyridine-1 monosulfofluorenyl] phenyl} 2- (4-mononitrobenzyl) -3-n-propyl-2,6-dihydro A 7H-pyrazolo [4,3-d] pyrimidin-7-one was prepared from the title compound of Preparation 9 6 and 1- (2-hydroxyethyl) hexahydropyridine according to the procedure of Example 1, showing Yellow oil (90%). 元素 Measured by elemental analysis: C, 5 4 · 8 3; Thallium, 5. 6 1; N, 15 · 46. C29H35N7〇7S; 54.88; H, 5.72; N, 15.45%. (5 (CDC 1 a): 0.96 (3H, t), 1 · 6 2 (3 H, t), 1 · 7 4 (2 H, m), 2 · 3 0 (1 H, s), 2 · 5 5 (2 H, t), 2. 6 0 (4 H , M), printed by the Consumer Cooperatives of the Central Standards Bureau of the Ministry of Economic Affairs (please read the precautions on the back before filling out this page) 2 · 9 0 (2 H, t), 3 · 1 0 (4 H, m), 3 · 5 8 (2 H, m), 4 · 3 9 (2 H, q), 5 · 6 4 (2 H, s), 7 · 1 7 (1 H, d), 7 · 3 3 (2 H , D), this paper size applies Chinese National Standard (CMS) A4 specification (210X 297 mm) -138-524805 A7 B7 V. Description of the invention (136) 7 · 8 2 (1 Η, d), 8.20 (2H , D), 8 · 7 8 (1 Η, s), 10.70 (lH, s). Example 9 3 2 — (4-Aminobenzyl) -5— [2-Ethoxy-5— (4-Methylhexaaminoorphine-1, 1-propanoate) phenyl] -3—n-propyl A 2,6-dihydro-7H-pyrazolo [4,3-d] pyrimidin-7-one was prepared from the title compound of Example 91 according to the procedure of Example 52, and was white foamy (77 %). Elemental analysis: 値: C, 5 8 · 5 1; Η, 6 · 1 8; N, 16 · 76. C28H35N7〇4S; 0 · 50H2 0 calculated 値 C, 58.52; Η, 6.31; N, 17.06%. δ (CDC 1 a): 0.83 (3H, t), 1 · 6 4 (3 H, t), 1 · 7 2 (2 H, m), printed by the Consumer Cooperative of the Central Standards Bureau of the Ministry of Economic Affairs (please read first Note on the back, please fill out this page again) 2 · 2 7 (3 H, s), 2 · 4 8 (4 H, m), 2 · 9 0 (2 H, t), 3 · 1 0 (4 H, m), 3 · 6 9 (2 H, s), 4. 3 6 (2 H ^ q), 5 · 4 3 (2 H, s), this paper size applies Chinese National Standard (CNS) A4 specification (210X297 (Mm) -139-524805 Λ7 B7 V. Description of the invention (137) 6 · 6 2 (2 Η, d), 7 · 〇6 (2 Η, d), 7 · 1 4 (1 Η, d), 7 8 0 (1 μm, d), 8 7 6 (1 μm, s), 10.58 (lH, s) ppm. Example 9 4 1- (N-ethylaminecarbonylmethyl) -5— [5— (4-methylhexaamine) —1—Sulfuryl—2—n-propoxyphenyl] —3 -N-propyl-1,6-dihydro-7H-pyrazolo [4,3-d] pyrazol-7-one was carried out from the title compound of Preparation Example 102 and 1-methylhexahydropyridine Prepared as described in Example 1 as a brown solid (40%). 5 (CDCl3): l.〇l (3H ^ t) ^ (Please read the notes on the back before filling this page) Printed by the Consumer Cooperatives of the Central Standards Bureau of the Ministry of Economic Affairs 2 2 2 2 3 3 hhhhhhhhh 332234242 rv rv / IV / IV / IV rv rv / l \ / (V 889489709 018024912 nm / \) y NMy \ My N) / \) y \) / \) / ttmmsmtmm This paper size applies to the Chinese National Standard (CNS) A4 specification (210X 297 mm) -140-524805 A7 B7 V. Description of the invention (138) 4 · 2 5 (2 Η, t), 5 · 2 3 (2 Η, s), 6 · 1 4 (1 Η, s), 7 · 1 8 (1 Η, d), 7 · 8 6 (1 Η, d), 8 · 8 7 (1 Η, s), 10.95 (lH, s). L R M S: m / z 56〇 (M + 1) +. Example 9 5 1- [N— (2-methoxyethyl) amine carbonylmethyl] -5— [5 — (4-methylhexahydrozine-1 1-mineral acid group)-2—n-propyl Oxyphenyl] -3 -n-propyl-1,6-dihydro-7H-pyrazolo [4, 3-d] pyrimidin-7-one was prepared from the title compound of Preparation Example 103 and 1-methylhexa Hydropyridine was prepared according to the procedure of Example 1 and was white foamy (63%). Printed by the Consumer Cooperatives of the Central Standards Bureau of the Ministry of Economic Affairs (please read the notes on the back before filling in this page) Elemental analysis and actual measurement 値: C, 5 4 · 60; Η, 6 · 8 7; N, 16.02 ° C27H39N7〇6S Calculate 値 C, 54.98; H, 6.67; N, 16.03%. (CDC 1 3): 1.05 (3H, t), 1.20 (3H, t), 1.89 (2H, m), 2.04 (2H, m), 2 · 2 9 (3 H, s), this paper size applies Chinese National Standard (CNS) A4 specification (210X 297 mm) -141-524805 A7 B7 V. Description of the invention (139) 2.50 (4H, m), 2 · 9 8 (2 Η, t), 3 · 1 〇 (4 Η, m), 3 · 3 3 (3 Η, s), 3 · 4 3 (4 Η, m), 4 · 2 9 (2 Η, t), 5. 2 8 (2 Η, s), 6 · 4 2 (1 Η, s), 7 · 1 8 (1 Η, d), 7 · 8 6 (1 Η, d), 8 8 8 (1 μm, s), 10.93 (lH, s) ° LRMS: m / z 590 (M + 1) +. Example 9 6 Printed by the Consumer Cooperatives of the Central Bureau of Standards of the Ministry of Economic Affairs (please read the precautions on the back before filling this page) 5 — [5 — (4-Hexamethylpyridine 1 1 sulfomethyl) 1 2-n-propoxyphenyl] -1- (morpholine-4-ylcarbonylmethyl) -3-n-propyl-1,6-dihydro-7H-pyrazolo [4,3-d] pyrimidine- 7-one was prepared from the title compound of Preparation Example 104 and 1-methylhexahydropyridine 1 according to the procedure of Example 1. It was a beige solid (59%). Elemental analysis found: C , 5 4 · 2 5; Η, 6 · 5 0; N, 14 · 72. C28H39N7〇6S; H2〇 Calculation: The paper size is applicable to Chinese National Standard (CNS) A4 (210X 297 mm) -142-524805 Printed by A7 B7, Consumer Cooperative of the Central Bureau of Standards of the Ministry of Economic Affairs 5. Description of the invention (14) C, 54.27; H, 6.67; N, 15.82%. 5 (CDCl3): 1.02 (3H, t), 1.19 (3 Η, t), 1.8.8 (2 Η, m), 2.0.02 (2 Η, m >, 2 · 2 7 (3 Η, s), 2. 5 0 (4 Η > m), 2 · 9 8 (2 Η, t), 3 · 1 2 (4 Η, m),. 3 · 5 6 ( 2 Η, m), 3 · 6 2 (2 Η, m), 3 · 7 3 (4 Η, m), 4 · 2 4 (2 Η, t), 5 · 4 5 (2 Η, .s) , 7 · 15 (1 Η, d), 7 · 8 3 (1 Η, d), 8.8 (1 Η, s), 1 · 8 7 (1 Η, s), LRMS: m / z 6〇2 (M + 1) +. Example 9 7 5 — [5 — (4-methylhexahydropyridine-1 1-sulfofluorenyl) — 2—n-propoxyphenyl] —1— [ 1 S — (morpholine-4 monoylcarbonyl) ethyl] -3 —n-propyl-1,6-dihydro-7H —pyrazolo [4 This paper is in accordance with Chinese National Standard (CNS) A4 (210X297) Mm) -143-(Please read the notes on the back before filling this page)

、1T 524805 at B7 五、發明説明（彳41) ，3 — d〕嘧啶—7 —酮 由製備例1 0 9之標題化合物及1 -甲基六氫吡哄依 例析 施分 實素 依元 N ο 8 N)y 5% . r—I 〇〇 6 ， (Η 體 ； 固 6 色 1—I 白 · 呈 5 ， 5 得 ， 製 C 驟 ： 步値 之測1T 524805 at B7 V. Description of the Invention (彳 41) 3-d] Pyrimidine-7-one The title compound and 1-methylhexahydropyridine from Preparation Example 10 were analyzed according to the examples. N ο 8 N) y 5%. R—I 〇〇6, (Η 体; solid 6 colors 1—I white · 5, 5 is obtained, making step C: step by step test

9 3 5 T—I 經濟部中央標準局員工消費合作社印製 c D0976808084768469 値 C278025914621188 · ^ιίί^ ο //—^\·*·······*··*·· cl) 計%51112222333467781 c 5 c 5 TT- ΤΊ* THX XHX THi XHX -Ji Ji ΤΊ* TT- THX THX THX THX THX ΤΓ- TF TF ΤΓ- THX Th- TF THX TF Trx ΤΓ- ΤΓ- XL1 ΤΓ 3322342426211119 3 5 T-I Printed by the Consumer Cooperatives of the Central Bureau of Standards of the Ministry of Economic Affairs c D0976808084768469 値 C278025914621188 · ^ ιίί ^ ο // — ^ \ · * ······ ** · ** · cl) Count% 51112222333467781 c 5 c 5 TT-TΊ * THX XHX THi XHX -Ji Ji TΊ * TT- THX THX THX THX THX ΤΓ- TF TF ΤΓ- THX Th- TF THX TF Trx ΤΓ- ΤΓ- XL1 ΤΓ 332234242621111

H C 2Η C 5 2 〇 5 6 〇 7Ν 4Η 9 3 5 一—IΝ 7 5 6Η 6 1-1 Η 3 /(V 2 〇 Ί-1 Φ—, (讀先閱讀背面之注意事項再填寫本頁) d m m s m mmmtQdds \ly \)/ \iy \)/ \)/ s 、\二口 4 本纸張尺度適用中國國家標準（CNS ) Α4規格（210Χ 297公釐）-144 - 524805 A7 B7 五、發明説明（142) LRMS :m/z 616 (M+l)+。 實施例9 8 5 —〔5— (4 —甲基六氫吡畊—1 一基磺醯基）一 2 —正丙氧苯基〕一 1 一〔 1R —嗎啉—4 一基猿基）乙 基〕—3 -正丙基—1 ，6 —二氫一7H —吡唑並〔4， 3 — d〕嘧啶—7 —酮 由製備例1 1 2之標題化合物及1 -甲基六氫吡哄依 實施例1之步驟製得，呈乳泡沫狀（5 4 % )。 元素分析實測値：C，5 6 · 2 6 ; Η，6 . 9 1 ; N， 15.2〇°C29H41N7〇6S計算値 C，56.57;N，6.7 1;N，15.92%。 (5(CDCl3)：l.〇〇(3H^t)> 1 · 2 0 ( 3 Η，t )， 1 · 7 9 ( 3 Η，d )， 1 · 8 7 ( 2 Η，m )， 2 ·〇 6 ( 2 Η，m )， 經濟部中央標準局員工消費合作社印製 r:· (請先閱讀背面之注意事項再填寫本頁) 2 · 2 7 ( 3 Η，s )， 2 · 5 6 ( 4 Η，m )， 2 · 9 7 ( 2 Η，t )， 3 · 1 〇（4 Η，m )， 3 · 4 8 ( 2 Η，m )， 3 · 6 4 ( 6 Η，m )， 4 · 2 7 ( 2 Η，t )， 本纸張尺度適用中國國家標準（CNS ) A4規格（210X 297公釐）-145 - 524805 經濟部中央標隼局員工消費合作杜印製 Α7 Β7 五、發明説明（143) 6 · 1 8 ( 1 Η，q )， 7 · 1 8 ( 1 Η，d )， 7 . 8 5 ( 1 Η，d )， 8 · 8 9 ( 1 Η，s )， l〇.9〇（lli，s)° LRMS:m/z 616(M+1)+。 實施例9 9 5 —〔5 —（4 一甲基六氫吡畊一 1 一基磺醯基）一 2 —正丙氧苯基〕一 1— (2 -嗎啉—4 一基乙基）一 3 —正丙基—1 ，6 —二氫—7H —吡唑並〔4，3 — d〕 嘧啶—7 -酮 由製備例1 1 4之標題化合物及1 -甲基六氫吡畊依 實施例1之步驟製得，呈白色固體（4 1 % )。 5(CDCl3):l.〇〇(3H，t) ， 1 · 2 〇（3 Η，t )， 1 . 8 6 ( 2 Η，m )， 2 · Ο 6 ( 2 Η，m )， 2 · 2 8 ( 3 Η，s )， 2 · 5 〇（8 Η，m )， 2 · 9 2 ( 4 Η，m )， 3 · 1 〇（4 Η，m )，’ 3 · 6 〇（4 Η，m )， 4 · 2 4 ( 2 Η ，t )， 本纸張尺度適用中國國家標準（CNS ) Α4規格（210X 297公釐）-146 - (請先閲讀背面之注意事項再填寫本頁) 4 、1Τ 經濟部中央標準局員工消費合作社印製 524805 A7 B7 五、發明説明（144) 4 · 6 8 ( 2 Η，t )， 7 · 1 7 ( 1 Η，d )， 7 · 8 2 ( 1 Η，d )， 8 · 8 8 ( 1 Η，s )， 1 〇· 8 4 ( 1 Η，s )。 L R M S ： m / z 589 (M+1)+。 實施例1〇0 5 —〔5 —（4 —乙基六氫吼哄一 1 一基磺醯基）一 2 -正丙氧苯基〕—1 一（2 —嗎啉一 4 —基乙基）一 3 —正丙基—1，6 —二氫一 7H —吡唑並，〔4，3 — d〕 嘧啶一 7 -酮 由製備例1 1 4之標題化合物及1 -乙基六氫吡畊依 實施例1之步驟製得，呈固體（3 6 % )。 元素分析實測値：C，5 7 · 4 4 ; Η，7 · 2 2 ; N， 15.86°C29H43N7〇5S 計算値 C，57.88;H，7.2〇；N，16.29%。 5 ( C D C 1 3 ) :l.〇〇（6H，m)， 1 · 1 8 ( 3 H，t )， 1 · 8 6 ( 2 H，m )， 2 · 0 4 ( 2 H，m )， 2 . 4 0 ( 2 H ^ q )， 2 · 5 2 ( 8 H，m )， 2 . 8 6 ( 2 H，t )， 本紙張尺度適用中國國家標準（CNS ) A4規格（210X 297公釐)~:147 (請先閱讀背面之注意事項再填寫本頁) 4HC 2Η C 5 2 〇5 6 〇7Ν 4Η 9 3 5 I—IN 7 5 6Η 6 1-1 Η 3 / (V 2 〇Ί-1 Φ—, (Read the precautions on the back before filling this page) dmmsm mmmtQdds \ ly \) / \ iy \) / \) / 4 2 The paper size is applicable to the Chinese National Standard (CNS) A4 specification (210 × 297 mm) -144-524805 A7 B7 V. Description of the invention (142) LRMS: m / z 616 (M + 1) +. Example 9 8 5-[5-(4-methylhexahydropyridine-1-1-sulfosulfanyl)-2-n-propoxyphenyl]-1-[1R -morpholine-4 -yl simyl) Ethyl] -3 -n-propyl-1,6-dihydro-7H-pyrazolo [4,3-d] pyrimidin-7-one was prepared from the title compound of Preparation Example 1 12 and 1-methylhexahydro Pyridoxine was prepared according to the procedure of Example 1 and was milk foamy (54%). Elemental analysis: 値: C, 5 6 · 2 6; Η, 6.9 1; N, 15.2 ° C 29H41N7〇6S Calculate 値 C, 56.57; N, 6.7 1; N, 15.92%. (5 (CDCl3): 1.0 × (3H ^ t) > 1 · 2 0 (3 Η, t), 1 · 7 9 (3 Η, d), 1 · 8 7 (2 Η, m), 2 · 〇6 (2 Η, m), printed by the Consumer Cooperatives of the Central Bureau of Standards of the Ministry of Economic Affairs: (Please read the notes on the back before filling out this page) 2 · 2 7 (3 Η, s), 2 · 5 6 (4 Η, m), 2 · 9 7 (2 Η, t), 3 · 1 〇 (4 Η, m), 3 · 4 8 (2 Η, m), 3 · 6 4 (6 Η, m), 4 · 2 7 (2 Η, t), this paper size applies the Chinese National Standard (CNS) A4 specification (210X 297 mm) -145-524805 Employees' cooperation cooperation of the Central Bureau of Standards, Ministry of Economic Affairs, printed Α7 Β7 V. Description of the invention (143) 6 · 1 8 (1 Η, q), 7 · 1 8 (1 Η, d), 7.8 5 (1 Η, d), 8 · 8 9 (1 Η, s ), L0.90 (lli, s) ° LRMS: m / z 616 (M + 1) +. Example 9 9 5 — [5 — (4-methylhexahydropyridine-1 1-sulfosulfonyl) Group)-2 -n-propoxyphenyl]-1-(2-morpholine-4 -ylethyl)-3-n-propyl-1, 6-dihydro-7H-pyrazolo [4, 3 — d) Pyrimidine-7-one is compounded by the title of Preparation Example 1 4 The compound and 1-methylhexahydropyridine were prepared according to the procedure of Example 1. It was a white solid (41%). 5 (CDCl3): 1.0 (3H, t), 1.2 (3 （) , T), 1. 8 6 (2 Η, m), 2 · Ο 6 (2 Η, m), 2 · 2 8 (3 Η, s), 2 · 5 〇 (8 Η, m), 2 · 9 2 (4 Η, m), 3 · 1 〇 (4 Η, m), '3 · 6 〇 (4 Η, m), 4 · 2 4 (2 Η, t), this paper scale applies to China Standard (CNS) Α4 Specification (210X 297 mm) -146-(Please read the precautions on the back before filling out this page) 4, 1T Printed by the Consumers Cooperative of the Central Standards Bureau of the Ministry of Economic Affairs 524805 A7 B7 V. Description of the invention (144 ) 4 · 6 8 (2 Η, t), 7 · 1 7 (1 Η, d), 7 · 8 2 (1 Η, d), 8 · 8 8 (1 Η, s), 1 〇 8 4 (1 Η, s). L R M S: m / z 589 (M + 1) +. Example 1 0 5-[5-(4-ethylhexahydrozine-1-1-sulfosulfanyl)-2- n-propoxyphenyl]-1-(2-morpholine 4- 4-ethyl ) A 3-n-propyl-1,6-dihydro-7H-pyrazolo, [4,3-d] pyrimidine-7-one from the title compound of Preparation Example 1 1 and 1-ethylhexahydropyridine It was prepared according to the procedure of Example 1 and was solid (36%). Elemental analysis: 値: C, 5 7 · 4 4; Η, 7 · 2 2; N, 15.86 ° C 29H43N7〇5S Calculate 値 C, 57.88; H, 7.20; N, 16.29%. 5 (CDC 1 3): 1.0 (6H, m), 1 · 18 (3 H, t), 1 · 8 6 (2 H, m), 2 · 0 4 (2 H, m), 2. 4 0 (2 H ^ q), 2 · 5 2 (8 H, m), 2. 8 6 (2 H, t), this paper size applies to China National Standard (CNS) A4 (210X 297 mm) ) ~: 147 (Please read the notes on the back before filling this page) 4

、1T 524805 A7 B7 五、發明説明（145) 2 · 9 〇（2 Η，t )， 3.10(4H，m)， 3 · 6 0 ( 4 Η，m )， 4 · 2 4 ( 2 Η，t )， 4 · 7 〇（2 Η，t )， 7 · 1 6 ( 1 Η，d )， 7 · 8 4 ( 1 Η，d )， 8 · 8 6 ( 1 Η，s )， 10.84(lH，s)。 L R M S ： m / z 6〇3(M+1)+。 實施例1〇1 5— { 5 —〔4— (2 —甲氧乙基）六氫吡畊一1 — 基磺酸基〕一 2 -正丙氧苯基} — 1一（2 —嗎啉—4 一 基乙基）一3 —正丙基一 1，6 —二氯—7H —吼β坐並〔 4，3 — d〕喃 D定—7 —醒 經濟部中央標準局員工消費合作社印製 (請先閱讀背面之注意事項再填寫本頁) 由製備例1 1 4之標題化合物及1 一（2 -甲氧乙基 )六氫吡哄依實施例1之步驟製得，呈白色固體（3 5 % )° 元素分析實測値：C，5 6 · 4 1 ; Η，7 . 1 1 ; N， 15 ·〇7 。 C3〇H45N7〇6S :〇.3〇H2〇計算値 C，56.55 ;H，7. 21 ;N，15.39%。 5 ( C D C 1 3 ) ： 1 . 0 0 ( 3 H ^ t )， 1 · 2 〇（3 H，t )， 本紙張尺度適用中國國家標準（CNS ) A4規格（210XN7公釐）~「48 : 524805 A7 B7 五、發明説明（146) 1 · 8 6 ( 2 Η，m )， 2.〇6(2H，m)， 2 · 5 〇（4 Η，m )， 2 · 5 8 ( 4 Η，m )， 2 · 8 6 ( 2 Η，t )， 2 · 9 4 ( 2 Η，t )， 3 · 1 〇（4 Η，m )， 3 · 2 8 ( 3 Η，s )， 3 · 4 2 ( 2 Η，t )， 3 · 6 〇（4 Η，m )， 4 · 2 4 ( 2 Η，t )， 4 · 7 〇（2 Η，t )， 7 · 1 4 ( 1 Η，d )， 7 · 8 2 ( 1 Η，d )， 8 · 8 4 ( 1 Η，s )， l〇.84(lH，s)。 L R M S ： m / z 633 (M+1)+。 經濟部中央標準局員工消費合作社印製 (請先閱讀背面之注意事項再填寫本頁) 實施例1〇2 2 — (N —乙基胺羰甲基）一5 —〔5 — (4 —甲基 六氫吡畊—1 一基磺醯基）一 2 —正丙氧苯基〕一 3 —正 丙基—2，6 —二氫—7H — D比d坐並〔4，3 — d〕喃0定 —7 -酮 由製備例1 0 5之標題化合物及1 -甲基六氫π比畊依 本紙張尺度適用中國國家標準（CNS ) A4規格（210X 297公釐）-149 - 524805 A7 B7 五、發明説明（147) 實施例1之步驟製得，呈乳泡沫狀（6 1 % )。 元素分析實測値：C，5 4 · 5 9 ; Η，6 · 6 2 ; N， 16 · 32。 C26H37N7〇5S ；〇· 7〇H2〇計算値 C，54.57;H，6.76;N，16.13%。 5(CDCl3):l.〇2(3H，t)， 1 · 1 〇（3 Η，t )， 1 · 2 Ο ( 3 Η，t )， 1 . 8 2 ( 2 Η，m )， 2 ·〇· 7 ( 2 Η，m )， 2 · 2 8 ( 3 Η，s )， 2.5〇（4H，m)， 3 ·〇〇（2 Η，t )， 3 · 1 1 ( 4 Η，m )， 3 · 2 9 ( 2 Η，m )， 4 · 2 6 ( 2 Η，t )， 4 · 9 9 ( 2 Η，s )， 6 · 2 3 ( 1 Η，s )， 7 · 1 7 ( 1 Η，d )， 7 · 8 6 ( 1 Η，d )， 8 · 8 2 ( 1 Η，s )， l〇.72(lH，s) 〇 LRMS :m/z 560 (M+l)+。 實施例1〇3 本紙張尺度適用中國國家標準（CNS ) A4規格（210X297公釐）-1 50 - (請先閱讀背面之注意事項再填寫本頁 訂 經濟部中央標準局員工消費合作社印製 524805 A7 B7 五、發明説明（148) 2 —〔N — (2 —甲氧乙基）胺羰甲基〕一5 —〔5 一（4一甲基六氫吡哄一1一基磺醯基）一2—正丙氧苯 基〕—3 —正丙基—2，6 -二氫—7H —吡唑並〔4， 3 — d〕喃D定—7 —酮 由製備例1 0 6之標題化合物及1 -甲基六氫吡哄依 實施例1之步驟製得，呈乳泡沬狀（5 4 % )。 元素分析實測値：C，5 4 · 6 7 ; Η，6 · 6 9 ; N， 15.89°C27H39N7〇6S 計算値 經濟部中央標準局員工消費合作社印製 9132234243422111 • /iv /iv /(V /X /l\ /(\ /l\ /l\ /(N ^\ r\ r\ /V /IV 4D75480000161873 5C18024013420318 y /—\ · · ··* · · · · · · · * · C511222333345677 8 h hhhhhhhhhhhhh Ίχ Η t \)/ \iy \)/ \)/ \)y \)ym m s m t m \)/ s m t s s d d % 3ο 6 一—IN 7 6 6 Η 3 /{V τ—Ηο 本紙張尺度適用中國國家標準（CNS ) A4規格（210X 297公釐）-151 - (請先閱讀背面之注意事項再填寫本頁) 524805 A7 B7 五、發明説明（149) 8 . 8 2 ( 1 Η，s )， 1 〇· 6 8 ( 1 Η，s )。 LRMS:m/z 59〇（M+1)+。 實施例1〇4 5 —〔5— (4 —甲基六氫吡哄一1—基磺醯基）— 2 —正丙氧苯基〕一 2 —（嗎啉—4 一基羰甲基）一 3 — 正丙基一 2，6 -二氫一 7H -吡唑並〔4，3 — d〕嘧 啶一 7 -酮 由製備例1 0 7之標題化合物及1 -甲基六氫吡哄依 實施例1之步驟製得，呈白色泡沬狀（5 2 % )。 元素分析實測ί値：（：，54·74;Η，6·46;Ν， 15 · 72 。 C28H39N7〇6S ; 〇 . 2OCH2C I2 計算値C，54.75;H，6.42;N， 15.85 % 。 (請先閱讀背面之注意事項再填寫本頁) 經濟部中央標準局員工消費合作社印製 x)y \)κ \ly \)χ Ν)/ \ly \)/ r—Η••tmmsmtmm NMy J1 Ji THX J1 -J1 HpH HjH 3ΤΚΧΤΓΤΓΤΓΤΓΤΓΤΓΤΓ 132234244 V rv /\ /l\ /' Γν /(V /(\ D 5 0 2 7 9 0 0 5 C19024016 511222333 Η 3 Γν 2 〇 本紙張尺度適用中國國家標準（CNS ) A4規格（210X 297公釐）_ 1 52 - 524805 A7 B7 五、發明説明（15〇) 3.72(4H，m)， 4 · 2 4 ( 2 Η，t )， 5 · 2 1 ( 2 Η，s )， 7 · 1 5 ( 1 Η，d )， 7 · 8 5 ( 1 Η，d )， 8 · 8 1 ( 1 Η，s )， l〇.58(lH，s)° LRMS:m/z 6〇2(M+1)+。 實施例1 0 5 5 —〔5—（4 一甲基六氫吡畊一 1—基磺醯基）— 2 -正丙氧苯基〕—2 -〔 1 S -（嗎啉—4 一基羰基） 乙基〕—3 —正丙基一 2，6 —二氫—7H —吡唑並〔4 ，3 — d〕嘧啶—7 —酮 由製備例1 1 0之標題化合物及1 -甲基六氫吡畊依 實施例1之步驟製得，呈白色泡沫狀（5 2 % )。 經濟部中央標準局員工消費合作社印製 (讀先閱讀背面之注意事項再填寫本頁) 元素分析實測値：C，5 4 · 5 7 ; Η，6 · 5 2 ; N， 15 · 15 。 CuH^NtOsS ； 〇 · 3 6 C Η 2 C 1 2 計算値C，54.56;H，6.51;N，15.17 %。 5(CDCl3):l.〇l(3H，t)， 1 · 1 5 ( 3 Η，t )， 1 · 8 2 ( 3 Η，d )， 1 · 8 8 ( 2 Η ，m )， 本紙張尺度適用中國國家標準（CNS ) A4規格（210X297公釐）-1 53 - 524805 Α7 Β7 五、發明説明（151) 2 ·〇 3 ( 2 Η，m )， 2 · 2 6 ( 3 Η，s )， 2 · 5 〇（4 Η，m )， 2 . 9 8 ( 2 Η，m )， 3 · 1 1 ( 4 Η，m )， 3 · 3 〇（2 Η，m )， 3 · 4 8 ( 2 Η，m )， 3 · 6 4 ( 4 Η，m )， 4.27(2H，mt)， 5 · 6 〇 ( 1 Η， Q )， 7 · 1 6 ( 1 Η， d )， 7 · 8 3 ( 1 Η， d )， 8 · 7 9 ( 1 Η， s )， 1〇 6 4 ( 1 Η S ) LRMS:m/z 616(M+1)+。 實施例1〇6 經濟部中央標準局員工消費合作社印製 (讀先閱讀背面之注意事項再填寫本頁) 5 —〔 5 —（4 一甲基六氫吡畊一 1—基磺醯基）一 2 —正丙氧苯基〕—2 -〔 1R—(嗎啉一 4 一基鑛基） 乙基〕—3 —正丙基一 2，6 —二氣一 7H — D比ti坐並〔4 ，3 — d〕喃D定一 7 -酮 由製備例1 1 3之標題化合物及1 -甲基六氫吡畊依 實施例1之步驟製得，呈黃色泡沬狀（5 4 % )。 元素分析實測値：C，5 5 · 5 5 ; Η，6 . 8 6 ; N， 本纸張尺度適用中國國家標準（CNS ) Α4規格（210X 297公釐）-154 - 524805 經濟部中央標準局員工消費合作社印製 A7 五、發明説明（152) 15 · 18 ；〇.1 6 C Η 2 C 1 2 計算値C，55.65;H，6.62;N， 15.58 %。 5(CDCl3):l.〇l(3H，t)， 1 · 1 3 ( 3 Η，t )， 1 . 8 2 ( 3 Η，d )， 1 · 9 0 ( 2 Η，m )， 2 ·〇 3 ( 2 Η，m )， ‘ 2 · 2 5 ( 3 Η，s )， 2 · 4 7 ( 4 Η，m )， 3 ·〇〇（2 Η ， m )， 3 ·〇 9 ( 4 Η，m )， 3 · 3 〇（2 Η，m )， 3 · 4 8 ( 2 Η，m )， 3 · 6 6 ( 4 Η，m )， 4. . 2 5 ( 2 H ^ t )， 5 · 5 9 ( 1 H，Q )， 7 · 1 7 ( 1 H，d )， 7 · 8 3 ( 1 H，d )， 8 · 8 〇（1 H，s )， l〇.63(lH，s)。 L R M S ： m / z 616(M+1)+。 實施例1〇7 本纸張尺度適用中國國家標準（CNS ) A4規格（21 OX 297公釐）-1 55 - (請先閱讀背面之注意事項再填寫本頁)1T 524805 A7 B7 V. Description of the invention (145) 2 · 9 0 (2 Η, t), 3.10 (4H, m), 3 · 6 0 (4 Η, m), 4 · 2 4 (2 Η, t ), 4 · 7〇 (2 Η, t), 7 · 16 (1 d, d), 7 · 8 4 (1 Η, d), 8 · 8 6 (1 Η, s), 10.84 (lH, s). L R M S: m / z 603 (M + 1) +. Example 10—5— [5 -— [4 -— (2-methoxyethyl) hexahydropyridine—1-sulfonic acid group] —2—n-propoxyphenyl group] —1— (2—morpholine —4 monoethyl) —3—n-propyl—1,6—dichloro—7H—roose β sits and [4,3 — d] Dan D—7—printed by the Consumer Cooperative of the Central Standards Bureau of the Ministry of Economic Affairs (Please read the precautions on the back before filling out this page). It was prepared from the title compound of Preparation Example 1 1 4 and 1- (2-methoxyethyl) hexahydropyridine according to the procedure of Example 1. It was a white solid. (35%) ° Measured by elemental analysis: C, 5 6 · 4 1; Thallium, 7. 1 1; N, 15 · 07. C3OH45N7〇6S: 0.30H2O calculated C, 56.55; H, 7.21; N, 15.39%. 5 (CDC 1 3): 1. 0 0 (3 H ^ t), 1 · 2 0 (3 H, t), this paper size applies Chinese National Standard (CNS) A4 specification (210XN7 mm) to "48: 524805 A7 B7 V. Description of the invention (146) 1 · 8 6 (2 Η, m), 2.〇6 (2H, m), 2 · 5 〇 (4 Η, m), 2 · 5 8 (4 Η, m), 2 · 8 6 (2 Η, t), 2 · 9 4 (2 Η, t), 3 · 1 〇 (4 Η, m), 3 · 2 8 (3 Η, s), 3 · 4 2 (2 Η, t), 3 · 6 〇 (4 Η, m), 4 · 2 4 (2 Η, t), 4 · 7 〇 (2 Η, t), 7 · 1 4 (1 Η, d ), 7 · 8 2 (1 Η, d), 8 · 8 4 (1 Η, s), 10.84 (lH, s). LRMS: m / z 633 (M + 1) +. Central Ministry of Economic Affairs Printed by the Consumer Bureau of the Standards Bureau (please read the precautions on the back before filling this page) Example 10 2-(N -ethylaminocarbonylmethyl) 5-[5-(4-methylhexahydro Pycnogenol-1 monosulfosulfanyl)-2-n-propoxyphenyl] -3-n-propyl-2,6-dihydro-7H — D than d sitting and [4,3 — d] —7-one from the title compound of Preparation Example 105 and 1-methyl Hexahydro π specific farming is based on the Chinese paper standard (CNS) A4 (210X 297 mm) -149-524805 A7 B7 according to the paper size. V. Description of the invention (147) It was prepared by the steps of Example 1 and was milk foam ( 6 1%). Elementary analysis: 値: C, 5 4 · 5 9; Η, 6 · 6 2; N, 16 · 32. C26H37N7〇5S; 〇7〇H2〇 Calculate 値 C, 54.57; H, 6.76 N, 16.13%. 5 (CDCl3): 1.02 (3H, t), 1.10 (3 Η, t), 1.20 (3 Η, t), 1.8 2 (2 Η , M), 2 · 0.7 · (2Η, m), 2 · 2 8 (3Η, s), 2.54 (4H, m), 3 · 〇〇 (2t, t), 3 · 1 1 (4 Η, m), 3 · 2 9 (2 Η, m), 4 · 2 6 (2 Η, t), 4 · 9 9 (2 Η, s), 6 · 2 3 (1 Η, s) , 7 · 1 7 (1 d, d), 7 · 8 6 (1 Η, d), 8 · 8 2 (1 Η, s), 10.72 (lH, s) 〇 LRMS: m / z 560 (M + l) +. Example 10: This paper size applies Chinese National Standard (CNS) A4 specification (210X297 mm)-1 50-(Please read the notes on the back before filling out this page. Printed by the Consumer Standards Cooperative of the Central Standards Bureau of the Ministry of Economic Affairs 524805 A7 B7 V. Description of the invention (148) 2 — [N — (2-methoxyethyl) aminocarbonylmethyl] —5— [5— (4-methylhexahydropyridine—1-ylsulfonyl) A 2-n-propoxyphenyl] -3 -n-propyl-2,6-dihydro-7H-pyrazolo [4, 3-d] -Dan-7-one was prepared from the title of Preparation Example 106 The compound and 1-methylhexahydropyridine were prepared according to the procedure of Example 1 and showed a vesicular shape (54%). Elemental analysis found 値: C, 5 4 · 6 7; Η, 6 · 6 9; N, 15.89 ° C27H39N7〇6S Computation 印 Printed by the Consumer Cooperatives of the Central Standards Bureau of the Ministry of Economic Affairs 9132234243422111 • / iv / iv / (V / X / l \ / (\ / l \ / l \ / (N ^ \ r \ r \ / V / IV 4D75480000161873 5C18024013420318 y / — \ · · · · · · · · · · · · * * C511222333345677 8 h hhhhhhhhhhhhh Ίχ Η t \) / \ iy \) / \) / \) y \) ym msmtm \) / smtssdd% 3ο 6 I—I N 7 6 6 Η 3 / {V τ—Ηο This paper size applies to Chinese National Standard (CNS) A4 specification (210X 297 mm) -151-(Please read the precautions on the back before filling this page) 524805 A7 B7 5 Description of the invention (149) 8. 8 2 (1 Η, s), 10.68 (1 Η, s). LRMS: m / z 59 ° (M + 1) +. Example 104 5— [5 -— (4-methylhexahydropyridine—1-sulfofluorenyl) —2-n-propoxyphenyl] —2— (morpholine-4 monocarbonylcarbonylmethyl) A 3-n-propyl-2,6-dihydro-7H-pyrazolo [4,3-d] pyrimidin-7-one was prepared from the title compound of Preparation Example 107 and 1-methylhexahydropyridine It was obtained by the procedure of Example 1 and was white foamy (52%). Elemental analysis and measurement: (:, 54 · 74; Η, 6.46; N, 15 · 72. C28H39N7〇6S; 〇2OCH2C I2 Calculate 値 C, 54.75; H, 6.42; N, 15.85%. (Please Read the notes on the back before filling this page) Printed by the Consumer Cooperatives of the Central Standards Bureau of the Ministry of Economic Affairs x) y \) κ \ ly \) χ Ν) / \ ly \) / r—Η •• tmmsmtmm NMy J1 Ji THX J1 -J1 HpH HjH 3ΤΚΧΤΓΤΓΤΓΤΓΤΓΤΓΤΓ 132234244 V rv / \ / l \ / 'Γν / (V / (\ D 5 0 2 7 9 0 0 5 C19024016 511222333 Η 3 Γν 2 〇 This paper standard applies to Chinese National Standard (CNS) A4 Specifications (210X 297mm) _ 1 52-524805 A7 B7 V. Description of the invention (15〇) 3.72 (4H, m), 4 · 2 4 (2 Η, t), 5 · 2 1 (2 Η, s) , 7 · 1 5 (1 Η, d), 7 · 8 5 (1 Η, d), 8 · 8 1 (1 Η, s), 10.58 (lH, s) ° LRMS: m / z 6 〇2 (M + 1) +. Example 1 0 5 5 — [5 -— (4-methylhexahydropyridine—1-sulfofluorenyl) — 2—n-propoxyphenyl] -2— [1 S-(morpholine-4 monocarbonyl) ethyl] -3 -n-propyl-2,6-dihydro-7H-pyrazolo [4,3-d] pyrimid Pyridin-7-one was prepared from the title compound of Preparation Example 1 10 and 1-methylhexahydropyridine according to the procedure of Example 1. It was a white foam (52%). Staff Cooperative of the Central Standards Bureau, Ministry of Economic Affairs Printed (read the precautions on the back and then fill out this page) Elemental analysis: 値: C, 5 4 · 5 7;;, 6 · 5 2; N, 15 · 15. CuH ^ NtOsS; 〇 · 3 6 C Η 2 C 1 2 Calculate 値 C, 54.56; H, 6.51; N, 15.17%. 5 (CDCl3): 1.0 (3H, t), 1 · 1 5 (3 Η, t), 1 · 8 2 (3 Η, d), 1 · 8 8 (2 Η, m), this paper size applies to China National Standard (CNS) A4 specification (210X297 mm) -1 53-524805 Α7 Β7 V. Description of the invention (151) 2 · 〇3 (2 Η, m), 2 · 2 6 (3 Η, s), 2 · 5 〇 (4 Η, m), 2.9 8 (2 Η, m), 3 · 1 1 (4 Η , M), 3 · 3 0 (2 Η, m), 3 · 4 8 (2 Η, m), 3 · 6 4 (4 Η, m), 4.27 (2H, mt), 5 · 6 〇 (1 Η, Q), 7 · 16 (1 Η, d), 7 · 8 3 (1 Η, d), 8 · 7 9 (1 Η, s), 106 · 4 (1 Η S) LRMS: m / z 616 (M + 1) +. Example 106 Printed by the Consumer Cooperatives of the Central Bureau of Standards of the Ministry of Economic Affairs (Read the precautions on the back before filling out this page) 5 — [5 — (4-methylhexahydropyridine 1-sulfosulfenyl) -2 -n-propoxyphenyl] -2-[1R— (morpholine-4 monophenyl) ethyl] -3—n-propyl-2,6—digas 7H — D than ti sit and [ 4, 3 — d] D-A-7-one was prepared from the title compound of Preparation 1 1 3 and 1-methylhexahydropyridine according to the procedure of Example 1, and showed a yellow foam (54%) . Elemental analysis: 値: C, 5 5 · 5 5; Η, 6. 8 6; N, This paper size applies to China National Standard (CNS) Α4 specification (210X 297 mm) -154-524805 Central Bureau of Standards, Ministry of Economic Affairs Printed by employee consumer cooperative A7 V. Description of invention (152) 15 · 18; 0.1 6 C Η 2 C 1 2 Calculate 値 C, 55.65; H, 6.62; N, 15.58%. 5 (CDCl3): 1.01 (3H, t), 1 · 1 3 (3 Η, t), 1.8 2 (3 Η, d), 1 · 9 0 (2 Η, m), 2 · 〇3 (2 Η, m), '2 · 2 5 (3 Η, s), 2 · 4 7 (4 Η, m), 3 · 〇 (2 Η, m), 3 · 〇 9 (4 Η , M), 3 · 3 0 (2 Η, m), 3 · 4 8 (2 Η, m), 3 · 6 6 (4 Η, m), 4.. 2 5 (2 H ^ t), 5 · 5 9 (1 H, Q), 7 · 1 7 (1 H, d), 7 · 8 3 (1 H, d), 8 · 8 〇 (1 H, s), 10.63 (1H, s). L R M S: m / z 616 (M + 1) +. Example 107 This paper size applies the Chinese National Standard (CNS) A4 specification (21 OX 297 mm) -1 55-(Please read the precautions on the back before filling this page)

、1T 524805 A7 B7 五、發明説明（彳53) 5 —〔5 —（4 —甲基六氫吡啡一1 一基磺醯基）— 2 —正丙氧苯基〕—2 -（2 —嗎啉一 4 —基乙基）一 3 —正丙基—2，6 —二氫一 7H —吡唑並〔4，3 - d〕 喃陡一 7 -酮 由製備例1 1 5之標題化合物及1 -甲基六氫吡畊依 實施例1之步驟製得，呈白色固體（5 2 % )。 元素分析實測値：C，5 6 · 4 4 ; Η，7 . 1 6 ; N， 16 ·〇7 。 C28H41N7〇5S ；〇· 5〇H2〇計算値 C，56.36;H，7.〇9;N，16.43%。 5(CDCl3):l.〇2(3H，t)， 1 · 1 2 ( 3 Η，t )， (請先閱讀背面之注意事項再填寫本頁) 經濟部中央標準局員工消費合作社印製 8280806206205 902591624188 · _···········cw 1222233447781, 1T 524805 A7 B7 V. Description of the invention (彳 53) 5 — [5 — (4-methylhexahydropyridine-1 1-ylsulfonyl) — 2 —n-propoxyphenyl] 2-(2 — Morpholine 4-ylethyl) -3-n-propyl-2,6-dihydro-7H-pyrazolo [4,3-d] anso-7-one from the title compound of Preparation Example 1 15 And 1-methylhexahydropyridine was prepared according to the procedure of Example 1 as a white solid (52%). Elemental analysis: 値: C, 5 6 · 4 4; Η, 7. 16; N, 16 · 07. C28H41N7〇5S; 0.50H2O calculated C, 56.36; H, 7.09; N, 16.43%. 5 (CDCl3): 1.02 (3H, t), 1 · 1 2 (3 Η, t), (Please read the notes on the back before filling this page) Printed by the Employees' Cooperatives of the Central Standards Bureau of the Ministry of Economic Affairs 8280806206205 902591624188 · _ ······· cw 1222233447781

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H s 本紙張尺度適用中國國家標準（CNS ) A4規格（210X 297公釐）-1 56 - 524805 A7 B7 五、發明説明（154) LRMS:m/z 58 9 (M+1)+。 實施例1 0 8 5 —〔5 —（4 一乙基六氫吡畊一 1 一基磺醯基）— 2 —正丙氧苯基〕一 2— (2 —嗎啉—4 —基乙基）—3 —正丙基—2，6 —二氫—7H —吡唑並〔4，3 — d〕 喃陡一 7 -酮 由製備例1 1 5之標題化合物及1 -乙基六氫吡畊依 實施例1之步驟製得，呈黃色油狀（2 4 % )。 元素分析實測値：C，5 7 · 0 4 ; Η，7 . 2 8 ; N， 15 · 46。C29H43N.〇5S ； 0 · 50H2〇計算値 C，57.〇3;H，7.26;N，16.〇5%。 5(CDCl3):l.〇4(3H，t)， 1 · 14 ( 3 Η，t )·， (請先閱讀背面之注意事項再填寫本頁) 經濟部中央標準局員工消費合作社印製 1222333447 T1 T1 Ji THX Ji THX Ji THX THX T_i ΤΓ- ΤΓ- ΤΓ_ ΤΓ_ ΤΓ_ ΤΓ_ ΤΓ ΤΓ ΤΓ 2228444221 /\ /(\ rv ,V /(\ /IV \ /IV /* 0400008304 9045016241 本紙張尺度適用中國國家標準（CNS ) A4規格（210X297公釐）-1 57 - 524805 A7 B7 五、發明説明（155) 7 · 8 2 ( 1 Η，d )， 8 · 8 〇（1 Η，s )， l〇.56(lH，s)° L R M S ： m / z 6〇3(M+1)+。 實施例1〇9 5— {5 —〔4— (2 —羥乙基）六氫吡畊—1—基 磺醯基〕一 2 -正丙氧苯基} — （2 —嗎啉一 4 一基 乙基）一3 -正丙基—2，6 -二氫—7H —吡唑並〔4 ，3 — d〕嘧啶—7 —酮 由製備例1 1 5之標題化合物及1 一（2 —羥乙基） 六氫吡哄依實施例1之步驟製得，呈白色固體（3 6 % ) 〇 元素分析實測値·· C，5 6 · 0 5 ; Η，7 · 0 2 ; Ν，15.31 °C29H43N7〇6S 計算値 (請先閱讀背面之注意事項再填寫本頁) 經濟部中央標準局員工消費合作社印製 8 3HHHHHHH 313221644 . c /l\ /l\ /(V /IV /IV /(V 6D4840806 5C 1 8 0 3 4 6 9 ， /.—\···*··· T—I 1X oo oo 〇〇 〇〇 oo N 2 〇 7 ΗH s This paper size applies to Chinese National Standard (CNS) A4 (210X 297 mm) -1 56-524805 A7 B7 V. Description of the invention (154) LRMS: m / z 58 9 (M + 1) +. Example 1 0 8 5 — [5 — (4-Ethylhexahydropyridine-1—1-sulfofluorenyl) — 2—n-propoxyphenyl] —2— (2-morpholine-4—ylethyl ) —3 —n-propyl-2,6 —dihydro — 7H —pyrazolo [4,3 — d] sulfan-7-one was prepared from the title compound of Preparation Example 1 15 and 1-ethylhexahydropyridine It was prepared according to the procedure of Example 1 and was yellow oily (24%). Elemental analysis: 値: C, 5 7 · 0 4; Η, 7. 2 8; N, 15 · 46. C29H43N.〇5S; 0.550H2O calculated C, 57.03; H, 7.26; N, 16.5%. 5 (CDCl3): 1.04 (3H, t), 1 · 14 (3 Η, t) ·, (Please read the notes on the back before filling out this page) Printed by the Consumer Cooperatives of the Central Standards Bureau of the Ministry of Economic Affairs 1222333447 T1 T1 Ji THX Ji THX Ji THX THX T_i ΤΓ- ΤΓ- ΤΓ_ ΤΓ_ ΤΓ_ ΤΓ_ ΤΓ ΤΓ ΤΓ 2228444221 / \ / (\ rv, V / (\ / IV \ / IV / * 0400008304 9045016241 This paper is in accordance with Chinese national standards ( CNS) A4 specification (210X297 mm) -1 57-524805 A7 B7 V. Description of the invention (155) 7 · 8 2 (1 Η, d), 8 · 8 〇 (1 Η, s), 10.56 ( lH, s) ° LRMS: m / z 6〇3 (M + 1) +. Example 1109 5— {5 — [4— (2-hydroxyethyl) hexahydropyrine—1—sulfosulfonium Yl]-2 -n-propoxyphenyl} — (2-morpholine 4 -ylethyl) — 3 -n-propyl-2,6-dihydro-7H —pyrazolo [4,3 — d] Pyrimidine-7-one was prepared from the title compound of Preparation Example 1 15 and 1- (2-hydroxyethyl) hexahydropyridine according to the procedure of Example 1 as a white solid (36%). Measured by elemental analysis. ·· C, 5 6 · 0 5; Η, 7 · 0 2; Ν, 15.31 ° C29H43N7〇6S Calculation 値 (Please read the notes on the back before filling out this page) Printed by the Consumer Cooperatives of the Central Standards Bureau of the Ministry of Economic Affairs 8 3HHHHHHH 313221644. C / l \ / l \ / (V / IV / IV / (V 6D4840806 5C 1 8 0 3 4 6 9, /.—\···*··· T—I 1X oo oo 〇〇〇〇oo N 2 〇7 Η

% 7 8 5 一—I Η 3 /- 4 ο r—i \)/ \)/ \\y \1/ m m s m m m 本纸張尺度適用中國國家標準（CNS ) A4規格（210X 297公釐）-1 58 - 524805 A7 B7 五、發明説明（彳56) 3 · 1 〇（4 Η，m )， 3 · 5 7 ( 2 Η，t )， 3 · 7 〇（4 Η，m )， 4 · 2 4 ( 2 Η，t )， 4 · 3 8 ( 2 Η，t )， 7 · 1 7 ( 1 Η，d )， 7 · 8 2 ( 1 Η，d )， 8 · 8 〇（1 Η，s )， l〇.60(lH，s)。 L R M S ： m / z 619 (M+l)+。 實施例1 1〇 2 —〔2 —（4 —甲基六氣11比哄一 1 一基）乙基〕一 5 —〔5 —（4 一甲基六氫吡啡—1—基磺醯基）一2 — 正丙氧苯基〕一 3 -正丙基—2，6 —二氫—7H -吡唑 並〔4，3 — d〕嘧啶—7 -酮 由製備例1 1 6之標題化合物及1 -甲基六氫吡畊依 實施例1之步驟製得，呈白色泡沫狀（4 3 % )。 經濟部中央標準局員工消費合作社印製 (請先閱讀背面之注意事項再填寫本頁) 元素分析實測値：C，5 6 · 2 0 ; Η，7 · 4 3 ; N， 17 · 78 。 C29H44N8〇4S ； 〇 . 2 0 C Η 2 C 1 2 計算値C，56.38;H，7.24;N，18.14 % 〇 5(CDCl3):l.〇2(3H，t)， 1 · 1 4 ( 3 Η ， t )， 本紙張尺度適用中國國家標準（CNS ) A4規格（21〇X 297公釐）-159 - 524805 Α7 Β7 五、發明説明（157) 1 · 8 6 ( 2 Η，m )， 2 ·〇 2 ( 2 Η，m )， 2 · 2 6 ( 3 Η，s )， 2 · 3 〇（3 Η，s )， 2 · 4 6 ( 8 Η，m )， 2 · 5 8 ( 4 Η，m )， 2 · 9 7 ( 4 Η，m )， 3 · 1 2 ( 4 Η，m )， 4.2〇（2H，t)， · 4 · 4 〇（2 Η，t )， 7 . 1 4 ( 1 Η，d )， 7 · 8 〇（1 Η，d )， 8 · 8 〇（1 Η，s )， l〇.55(lH，s)° LRMS:m/z 602(M+1) +。 實施例1 1 1 5 —〔 5 —（ 4 一乙基六氫吼哄一 1 —基擴醯基）一 2 —正丙氧苯基〕一 3 -正丙基一 2 — (2 -吡唑一 1一 基乙基）一2，6 —二氫—7H —吡唑並〔4，3 — d〕 嘧啶—7 —酮 由製備例1 1 8之標題化合物及1 一乙基六氫吡畊依 實施例1之步驟製得，呈白色泡沫狀（4 5 % )。 元素分析實測値：C，5 7 · 6 2 ; Η，6 · 5 9 ; N， 本紙張尺度適用中國國家標準（CNS ) A4規格（210X297公釐）-160 - (請先閱讀背面之注意事項再填寫本頁 、\呑 經濟部中央標準局員工消費合作社印製 524805 kl B7 五、發明説明（彳58) 19.05°C28H38N8〇4S 計算値 經濟部中央標準局員工消費合作社印製 7 D 81488 4800462684906 5C91493440267080577 . ， ✓/—\·*·*····*···*···· cw C5011122234446677781% 7 8 5 I—I Η 3 /-4 ο r—i \) / \) / \\ y \ 1 / mmsmmm This paper size applies to China National Standard (CNS) A4 specification (210X 297 mm) -1 58-524805 A7 B7 V. Description of the invention (彳 56) 3 · 1 〇 (4 Η, m), 3 · 5 7 (2 Η, t), 3 · 7 〇 (4 Η, m), 4 · 2 4 (2 Η, t), 4 · 3 8 (2 Η, t), 7 · 1 7 (1 Η, d), 7 · 8 2 (1 Η, d), 8 · 8 〇 (1 Η, s) , 10.60 (lH, s). L R M S: m / z 619 (M + 1) +. Example 1 102- [2- (4-methylhexazine 11 to 1-11-yl) ethyl] -5- [5 — (4-methylhexahydropyridin-1-ylsulfonyl) ) A 2-n-propoxyphenyl] -3-n-propyl-2,6-dihydro-7H-pyrazolo [4,3-d] pyrimidin-7-one from the title compound of Preparation Example 1 16 And 1-methylhexahydropyridine was prepared according to the procedure of Example 1 and showed a white foam (43%). Printed by the Consumer Cooperatives of the Central Standards Bureau of the Ministry of Economic Affairs (please read the precautions on the back before filling out this page) Elemental analysis and actual measurement 値: C, 5 6 · 2 0; Η, 7 · 4 3; N, 17 · 78. C29H44N8〇4S; 0.20 C Η 2 C 1 2 Calculate 値 C, 56.38; H, 7.24; N, 18.14% 〇5 (CDCl3): 1.0 (3H, t), 1 · 1 4 (3 Η, t), this paper size applies to Chinese National Standard (CNS) A4 specification (21 × 297 mm) -159-524805 Α7 Β7 V. Description of the invention (157) 1 · 8 6 (2 Η, m), 2 · 〇2 (2 Η, m), 2 · 2 6 (3 Η, s), 2 · 3 〇 (3 Η, s), 2 · 4 6 (8 Η, m), 2 · 5 8 (4 Η , M), 2 · 9 7 (4 Η, m), 3 · 1 2 (4 Η, m), 4.2 0 (2H, t), · 4 · 4 〇 (2 Η, t), 7. 1 4 (1 Η, d), 7 8 8 (1 Η, d), 8 · 8 (1 Η, s), 10.55 (1H, s) ° LRMS: m / z 602 (M + 1) +. Example 1 1 1 5 — [5 — (4-ethylhexahydrozine) —1- 1-propanyl] —2-n-propoxyphenyl] 3—n-propyl-2— (2-pyrazole 1-11-ylethyl) -2,6-dihydro-7H-pyrazolo [4,3-d] pyrimidin-7-one was prepared from the title compound of Preparation Example 1 1 and 1-ethylhexahydropyridine It was prepared according to the procedure of Example 1 and was white foam (45%). Elemental analysis: ，: C, 5 7 · 6 2; Η, 6 · 5 9; N, This paper size is applicable to China National Standard (CNS) A4 (210X297 mm) -160-(Please read the precautions on the back first Fill out this page again, printed by the Consumers' Cooperatives of the Central Standards Bureau of the Ministry of Economic Affairs 524805 kl B7 V. Description of Invention (彳 58) 19.05 ° C28H38N8〇4S Calculated by the Consumers Cooperatives of the Central Standards Bureau of the Ministry of Economics 7 D 81488 4800462684906 5C91493440267080577 ., ✓ / — \ · * · * ··· * ·· ** ···· cw C5011122234446677781

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m sM R L Η z +M /—v 3 8 5 2 r—I r—j例施 本紙張尺度適用中國國家標率（CNS ) A4規格（210X297公釐）-161 - 524805 A7 五、發明説明（159) 5 -〔 5 — ( 4 —乙基六氣吼畊—1 —基擴醯基）— 2 —正丙氧苯基〕一 3 —正丙基一 2 -〔2— (1 ，2， 3 —三唑一1—基）乙基〕—2 ，6 —二氫一 7H —吡唑 並〔4，3 - d〕嘧啶一 7 -酮 由製備例1 2 0之標題化合物及1 -乙基六氫吡啡依 實施例1之步驟製得，呈白色泡沬狀（5 7 % )。 元素分析實測値：C，5 5 · 1 3 ; Η，6 · 4 4 ; N， 21.41°C27H37N9〇4S 計算値 C，55.56;H，6.39;N，21.60%。 5(CDCl3):〇.82(3H，t)， 0 . 9 6 ( 3 Η，t )， 1 · 1 4 ( 3 Η，t )， 1 · 5 1 ( 2 Η，m )， 2 · 0 〇（2 Η，m )， 2 . 3 8 ( 2 Η，m )， 2 · 5 0 ( 4 Η，m )， 2 . 5 8 ( 2 Η，t )， 經濟部中央標準局員工消費合作社印製 (請先閲讀背面之注意事項再填寫本頁) 3 · 0 4 ( 4 Η，m )， 4 · 2 〇（2 Η，t )， 4 · 7 6 ( 2 Η，t )， 5 ·〇 4 ( 2 Η，t )， 7 · Ί 5 ( 2 Η，d )， 7 . 6 3 ( 1 Η，s )， 7 · 8 〇（2 Η，d )， 本紙張尺度適用中國國家標準（CNS ) Α4規格（21 ΟΧ 297公釐）-162 - 524805 A7 B7 五、發明説明（160) 8 · 7 2 ( 1 Η，s )， 1 〇.5 8 ( 1 Η，s )。 LRMS:m/z 5 8 4 (M+1)+。 實施例1 1 3 5 —〔5 — (4 —甲基六氫吡畊一 1—基磺醯基）— 2 -正丙氧苯基〕—3 -正丙基—2 —〔2 — (1，2， 4 —三唑一 1 —基）乙基〕—2，6 —二氫—7 Η —吡唑 並〔4，3 — d〕嘧啶—7 -酮 由製備例1 2 2之標題化合物及1 -甲基六氫吡哄依 實施例1之步驟製得，呈白色固體（33%)。 元素分析實測値：C，5 4 · 5 8 ; Η，6 · 2 4 ; N， 21.57°C26H35N9〇4S 計算値 C，54.82;H，6.19;N，22.13%。 5(CDCl3):〇.86(3H，t) ， 1 · 1 3 ( 3 Η，t )， 1 · 5 5 ( 2 Η ，m )， (請先閱讀背面之注意事項再填寫本頁 - 訂 經濟部中央標率局員工消費合作社印製 0 4 6 2 8 2 0 0 2 4 6 0 2 7 2 2 2 2 3 4 4 /l\ '、 \]y \Jy \J \)y \iy \Jy \]y m s m t m t t y 9- y y y ? m7 THX T_i THX _J1 THX Tr_ Tr_ THi T_i T_i Trx Tr_ 2 3 4 2 4 2 2 本紙張尺度適用中國國家標準（CNS ) A4規格（210X 297公釐）-163 - 經濟部中央標準局員工消費合作社印製 524805 A7 B7 五、發明説明（161) 4 . 9 〇（2 Η，t )， 7 · 1 2 ( 1 Η，d )， 7 · 6 6 ( 1 Η，s )， 7 · 7 8 ( 1 Η，d )， 7 · 9 2 ( 1 Η，s )， 8 · 7 〇（1 Η，s )， 1 〇· 6 0 ( 1 Η，s )。 LRMS :m/z 57〇（M+1)+。 實施例1 1 4 5 —〔 5 —（ 4 一乙基六氫批哄—1 一基擴醯基）一 2 —正丙氧苯基〕—3 —正丙基一 2 —〔2 -（1，2， 4 —三唑—1—基）乙基〕—2，6 —二氫—7H —吡唑 並〔4，3 — d〕嘧啶—7 —酮 由製備例1 2 2之標題化合物及1 -乙基六氫吡哄依 實施例1之步驟製得，呈白色固體（3 7 % )。 元素分析實測値：C，5 5 · 1 4 ; Η，6 · 3 7 ; N， 2 1 . 1 4。C 2 7 Η 3 7 Ν 9 〇 4 S 計算値 C，55.56;H，6.39;N，21.6〇％。 5 ( C D C 1 3 ):〇.87(3H，t)， 〇· 9 8 ( 3 Η，m )， 1 · 1 4 ( 3 Η，t )， 1 . 5 7 ( 2 Η，m )， 2 · 0 〇（2 Η，m )， 本纸張尺度適用中國國家標準（CNS ) A4規格（210X 297公釐）-1 64 - (讀先閱讀背面之注意事項再填寫本頁)m sM RL Η z + M / —v 3 8 5 2 r—I r—j Example application This paper size is applicable to China National Standard (CNS) A4 specification (210X297 mm) -161-524805 A7 V. Description of the invention ( 159) 5-[5 — (4 -Ethylhexazine-1 -yl-based fluorenyl)-2 -n-propoxyphenyl]-3 -n-propyl- 2-[2-(1, 2, 3-triazol-1-yl) ethyl] -2,6-dihydro-7H-pyrazolo [4,3-d] pyrimidin-7-one was prepared from the title compound of Preparation Example 1 2 and 1-ethyl Hexahydropyridine was prepared according to the procedure of Example 1 and was white foamy (57%). Elemental analysis: 値: C, 5 5 · 1 3; Η, 6 · 4 4; N, 21.41 ° C 27H37N9004S Calculate 値 C, 55.56; H, 6.39; N, 21.60%. 5 (CDCl3): 0.82 (3H, t), 0.96 (3 Η, t), 1 · 1 4 (3 Η, t), 1 · 5 1 (2 Η, m), 2 · 0 〇 (2 Η, m), 2. 3 8 (2 Η, m), 2. · 5 0 (4 Η, m), 2. 5 8 (2 Η, t), printed by the Staff Consumer Cooperative of the Central Standards Bureau of the Ministry of Economic Affairs System (please read the notes on the back before filling this page) 3 · 0 4 (4 Η, m), 4 · 2 〇 (2 Η, t), 4 · 7 6 (2 Η, t), 5 · 〇 4 (2 Η, t), 7 · Ί 5 (2 Η, d), 7. 6 3 (1 Η, s), 7 · 8 〇 (2 Η, d), this paper size applies Chinese National Standard (CNS ) Α4 specification (21 〇 × 297 mm) -162-524805 A7 B7 V. Description of the invention (160) 8 · 7 2 (1 Η, s), 1 0.5 8 (1 Η, s). LRMS: m / z 5 8 4 (M + 1) +. Example 1 1 3 5 — [5 — (4-methylhexahydropyridine-1-ylsulfonyl) — 2 —n-propoxyphenyl] 3 —n-propyl-2 — [2 — (1 , 2,4-triazol-1-yl) ethyl] -2,6-dihydro-7 pyrene-pyrazolo [4,3-d] pyrimidin-7-one From the title compound of Preparation Example 1 2 2 And 1-methylhexahydropyridine was prepared according to the procedure of Example 1 as a white solid (33%). Elemental analysis: 値: C, 5 4 · 5 8; Η, 6 · 2 4; N, 21.57 ° C 26H35N9〇4S Calculate 値 C, 54.82; H, 6.19; N, 22.13%. 5 (CDCl3): 0.86 (3H, t), 1 · 1 3 (3 Η, t), 1 · 5 5 (2 Η, m), (Please read the notes on the back before filling out this page-Order Printed by the Consumer Cooperatives of the Central Standards Bureau of the Ministry of Economic Affairs 0 4 6 2 8 2 0 0 2 4 6 0 2 7 2 2 2 2 3 4 4 / l \ ', \] y \ Jy \ J \) y \ iy \ Jy \] ymsmtmtty 9- yyy? M7 THX T_i THX _J1 THX Tr_ Tr_ THi T_i T_i Trx Tr_ 2 3 4 2 4 2 2 This paper size applies the Chinese National Standard (CNS) A4 specification (210X 297 mm) -163-Economy Printed by the Consumers' Cooperative of the Central Standards Bureau of the Ministry of Education 524805 A7 B7 V. Description of the invention (161) 4. 9.0 (2 Η, t), 7 · 1 2 (1 Η, d), 7 · 6 6 (1 Η, s ), 7 · 7 8 (1 Η, d), 7 · 9 2 (1 Η, s), 8 · 7 〇 (1 Η, s), 1 〇 6 0 (1 Η, s). LRMS: m / z 57 ° (M + 1) +. Example 1 1 4 5 — [5 — (4-Ethylhexahydropropanyl— 1 1-based fluorenyl) — 2 —n-propoxyphenyl] 3 —n-propyl- 2 — [2-(1 , 2,4-triazol-1-yl) ethyl] -2,6-dihydro-7H-pyrazolo [4,3-d] pyrimidin-7-one was prepared from the title compound of Preparation Example 1 2 2 and 1-Ethylhexahydropyridine was prepared according to the procedure of Example 1 as a white solid (37%). Elemental analysis: 値: C, 5 5 · 1 4; Η, 6 · 3 7; N, 2 1. 1 4. C 2 7 Η 3 7 Ν 9 〇 4 S Calculate 値 C, 55.56; H, 6.39; N, 21.60%. 5 (CDC 1 3): 0.87 (3H, t), 0.98 (3 Η, m), 1.14 (3 Η, t), 1.57 (2 Η, m), 2 · 0 〇 (2 Η, m), this paper size applies Chinese National Standard (CNS) A4 specification (210X 297 mm)-1 64-(Read the precautions on the back before filling in this page)

524805 kl B7 五、發明説明（162) 2.38(2H，m)， 2.5〇（4H，m)， 2 . 6 2 ( 2 Η，t )， 3 ·〇 5 ( 4 Η，m )， 4 · 2 2 ( 2 Η，t )， 4 · 6 8 ( 2 Η，t )， 4 · 8 8 ( 2 Η，t )， 7 · 1 2 ( 1 Η，d )， 7 · 6 6 ( 1 Η，s )， 7 · 8 Ο ( 1 Η，d )， 7 · 9 2 ( 1 Η，s )， 8 · 7 Ο ( 1 Η，s )， 10.6〇（lH，s)° L R Μ S ： m / ζ 584 (M+1)+。 實施例1 1 5 經濟部中央標準局員工消費合作社印製 (請先閲讀背面之注意事項再填寫本頁) 5 —〔5— (4 —乙基六氫吡畊一1 一基磺醯基）一 2 —正丙氧苯基〕一 2 — (2 -硝苯基）一 3 —正丙基一 2 ’ 6 — —^氣—7H—D比嗤並〔4，3 — d〕喃D定一 7 — 酮 由製備例1 2 3之標題化合物及1 -乙基六氫吡畊依 實施例1之步驟製得，呈黃色泡沬狀（3 6 % )。 5 ( C D C 1 a ):〇.9〇（3H，t)， 〇· 9 9. ( 3 Η ，m )， 本紙張尺度適用中國國家標準（CNS ) A4規格（210X297公釐）-165 - 524805 A7 B7 五、發明説明（彳63) 1 .1 1 ( 3 Η， t )， 1 • 7 5 ( 2 Η， m )， 2 •〇 2 ( 2 Η， m )， 2 .3 8 ( 2 Η， m )， 2 • 5 〇 ( 4 Η， m )， 2 .8 5 ( 3 Η， t )， 3 •〇 8 ( 4 Η ， m )， 4 • 2 〇 ( 2 Η， t )， 7 .1 3 ( 1 Η， d )， 7 • 5 8 ( 1 Η， d )， 7 • 7 4 ( 3 Η， m )， 8 .1 7 ( 1 Η， d )， 8 • 8 2 ( 1 Η， s )， 1 0 . 6 4 ( 1 Η S ) (讀先閱讀背面之注意事項再填寫本頁 .衣. 訂 LRMS:m/z 610(M+1)+。 實施例1 1 6 經濟部中央標準局員工消費合作社印製 2— (2 —胺苯基）—5 —〔5— (4 —乙基六氫吡 畊一 1 一基磺醯基）—2 -正丙氧苯基〕一 3 -正丙基— 2，6 —二氫一 7H — d 比 n坐並〔4，3 — d〕嚼D定—7 — 酮 在345kPa (5〇psi)及5〇°C下將含有實 施例115標題化合物（622mg，1 · 〇2mmo 1 )，1〇％銷（於木炭上）（l〇〇mg)，乙醇（1〇 本紙張尺度適用中國國家標準（CNS ) A4規格（210X297公釐）_ 1 66 - 524805 經濟部中央標準局員工消費合作社印繁 A7 B7 五、發明説明（彳64) m 1 )及乙酸乙酯（3 0 m 1 )的攪拌混合物氫化3小時 ，然後在室溫下氫化1 8小時。混合物經過濾後將濾液與 乙酸乙酯對濾片沖洗所得洗液加以合倂，減壓蒸發後得到 呈白色粉末之標題化合物（100%)。 ά ( C D C 1 a ):〇.87(3H，t)， 〇 · 9 8 ( 3 Η，m )， 1 · 1 2 ( 3 Η，t )， 1 · 7 0 ( 2 Η，m )， 2 ·〇 1 ( 2 Η，q )， 2.38(2H，m)， 2 · 4 8 ( 4 H，m )， 2 · 9 〇（2 H，t )， 3 · 0 8 ( 4 H，m )， 3 · 9 2 ( 2 H，s )， 4 · 2 3 ( 2 H，t )， 6 · 8 6 ( 2 H，d )， 7 · 1 3 ( 2 H，d )， 7 · 2 7 ( 1 H，d )， 7 · 8 1 ( 1 H，d )， 8 · 8 〇（1 H，s )， 10.62(lH，s)。 L R M S ： m / z 580 (M+1)+。 實施例1 1 7 本紙張尺度適用中國國家標準（CNS ) A4規格（210X297公釐）-1 67 - (讀先閱讀背面之注意事項再填寫本頁)524805 kl B7 V. Description of the invention (162) 2.38 (2H, m), 2.50 (4H, m), 2.62 (2Η, t), 3 · 05 (4Η, m), 4 · 2 2 (2 Η, t), 4 · 6 8 (2 Η, t), 4 · 8 8 (2 Η, t), 7 · 1 2 (1 Η, d), 7 · 6 6 (1 Η, s ), 7 · 8 Ο (1 Η, d), 7 · 9 2 (1 Η, s), 8 · 7 Ο (1 Η, s), 10.6 (1H, s) ° LR Μ S: m / ζ 584 (M + 1) +. Example 1 1 5 Printed by the Consumer Cooperatives of the Central Bureau of Standards of the Ministry of Economic Affairs (please read the precautions on the back before filling out this page) -2 -n-propoxyphenyl]-2-(2-nitrophenyl)-3-n-propyl-2 '6--^ gas-7H-D than pyrene [4,3 — d] A 7-one was prepared from the title compound of Preparation Example 1 2 3 and 1-ethylhexahydropyridine according to the procedure of Example 1 and was yellow foamy (36%). 5 (CDC 1 a): 0.90 (3H, t), 0.99 (3 Η, m), this paper size applies Chinese National Standard (CNS) A4 specification (210X297 mm) -165-524805 A7 B7 V. Description of the invention (彳 63) 1.1 1 (3 Η, t), 1 • 7 5 (2 Η, m), 2 • 〇2 (2 Η, m), 2. 3 8 (2 Η , M), 2 • 5 0 (4 Η, m), 2. 8 5 (3 Η, t), 3 • 0 8 (4 Η, m), 4 • 2 〇 (2 Η, t), 7. 1 3 (1 Η, d), 7 • 5 8 (1 Η, d), 7 • 7 4 (3 Η, m), 8. 1 7 (1 Η, d), 8 • 8 2 (1 Η, s), 1 0. 6 4 (1 Η S) (Read the notes on the back before filling in this page. Clothes. Order LRMS: m / z 610 (M + 1) +. Example 1 1 6 Central Ministry of Economic Affairs Printed by the Consumer Bureau of Standards Bureau 2— (2-Aminephenyl) —5— [5— (4-Ethylhexahydropyridine-1—1-sulfofluorenyl) —2—n-propoxyphenyl] -3 -N-propyl-2,6-dihydro-7H-d than n-sit and [4,3-d] chelate D-7-7-ketone will contain examples at 345kPa (50psi) and 50 ° C 115 title compound (622m g, 1.02mmo 1), 10% sold (on charcoal) (100mg), ethanol (10 paper sizes apply Chinese National Standard (CNS) A4 specifications (210X297 mm) _ 1 66- 524805 Employees' Cooperatives of the Central Bureau of Standards, Ministry of Economic Affairs, Consumer Cooperatives, Infanches A7 B7 V. Description of the invention (彳 64) m 1) and ethyl acetate (30 m 1) The hydrogenated mixture was hydrogenated for 3 hours, and then hydrogenated at room temperature for 18 hours The mixture was filtered, and the filtrate and ethyl acetate were combined to wash the washings from the filter. The title compound (100%) was obtained as a white powder after evaporation under reduced pressure. (CDC 1 a): 0.87 (3H , T), 0.98 (3 Η, m), 1 · 1 2 (3 Η, t), 1 · 7 0 (2 Η, m), 2 · 〇1 (2 Η, q), 2.38 ( 2H, m), 2 · 4 8 (4 H, m), 2 · 9 0 (2 H, t), 3 · 0 8 (4 H, m), 3 · 9 2 (2 H, s), 4 · 2 3 (2 H, t), 6 · 8 6 (2 H, d), 7 · 1 3 (2 H, d), 7 · 2 7 (1 H, d), 7 · 8 1 (1 H , D), 8.8 (1 H, s), 10.62 (1 H, s). L R M S: m / z 580 (M + 1) +. Example 1 1 7 This paper size applies Chinese National Standard (CNS) A4 specification (210X297 mm) -1 67-(Read the precautions on the back before filling this page)

經濟部中央標準局員工消費合作社印製 524805 Μ ^__ϋ-- 五、發明説明（165) 5 —〔5_ (4 一乙基六氫吡畊一 1 一基磺醯基）— 2〜正丙氧苯基〕一 2 -（2 —甲烷磺醯胺苯基）一 3 一 正丙基—2，6-二氫一 7Η -吡唑並〔4，3 - d〕嘧 啶一 7 —酮 在氮氣下將甲烷磺醯氯（0 . 1 5 6 m 1 ’ 2 · 0 m m ο 1 )加入一攪拌中而含有實施例1 1 6標題化合物 (583mg ，1 · 〇mm〇 1)及吡啶（8ml)之溶 液裡，於5 0 °C下將整個溶液攪拌1 8小時，然後減壓蒸 發。令殘餘物於乙酸乙酯及水之間分配，分出的有機相以 鹽水洗之並乾燥（N a 2 S 0 4 )後再減壓蒸發。生成的棕 色海綿狀物質以管柱層析法利用二氯甲烷：甲醇（1 0 0 :〇至99 : 1至98 : 2至97 : 3)之沖提梯度在矽 膠上加以純化而得到呈乳泡沬狀的標題化合物（3 2 % ) 〇 元素分析實測値：c，5 3 · 9 6 ; Η，6 · 0 1 ; N， 14· 38 。C 3〇H39N7〇6S2 ;〇· 6〇H2〇計算 値 C，53.89;H，6.〇6;N，1467%。 5 ( C D C 1 3 ):〇.91(3H，t)， 1 · 0 1 ( 3 Η，t )， 1 · 1 9 ( 3 Η，t )， 1 . 7 5 ( 2 Η，m )， 2 ·〇 7 ( 2 Η，m )， 2 · 4 0 ( 2 Η，q )， 2 · 5 3 ( 4 Η，m )， 本紙張尺度適用中國國家標準（CNS ) A4規格（210X297公釐）~「168 - 一 (請先閱讀背面之注意事項再填寫本頁) 訂 4 524805 Α7 Β7 五、發明説明（166) 2 . 9 3 ( 2 Η，t )， 3 ·〇 7 ( 3 Η，s )， 3 ·〇 9 ( 4 Η，m )， 4 . 2 9 ( 2 Η，t )， 7 · 1 6 ( 2 Η，m )， 7 · 3 5 ( 2 Η，m )， 7 · 5 7 ( 1 Η，t )， 7 · 8 2 ( 2 Η，d )， 8 · 8 〇（1 Η，s )， l〇.74(lH，s)。 L R M S ： m / z 658(M+1)+。 實施例1 1 8 經濟部中央標準局員工消費合作社印製 (請先閱讀背面之注意事項再填寫本頁) 5 —〔5 —（4 一甲基六氫吡畊—1—基磺醯基）一 2 -正丙氧苯基〕—2 — (4 —硝基）—3 -正丙基一 2 ，6 —二氫一 7H —吡唑並〔4，3 — d〕嘧啶一 7 —酮 由製備例1 2 4之標題化合物及1 -甲基六氫吡畊依 實施例1之步驟製得，呈黃色泡沬狀（6 3 % )。 5 ( C D C 1 3 ):〇.96(3H，t); 1 · 1 6 ( 3 Η，t )， 1 · 8 〇（2 Η，m )， 2 · Ο 5 ( 2 Η，m )， 2 · 2 7 ( 3 Η，s )， 2 · 4 9 ( 4 Η ，m )， 本紙張尺度適用中國國家標準（CNS ) A4規格（210X 297公釐） -169- 經濟部中央標準局員工消費合作社印製 524805 A7 B7 五、發明説明（167) 3 . 1 0 ( 6 Η，m )， 4.27(2H，t)， 7 · 1 8 ( 1 Η，d )， 7 · 8 3 ( 2 Η，d )， 7 · 8 6 ( 1 Η，d )， 8 · 4 6 ( 2 Η，d )， 8 · 8 4 ( 1 Η，s )， l〇.75(lH，s)。 LRMS:m/z 596 (M+1)+。 實施例1 1 9 2 —（4 一胺苯基）一 5 —〔5 — (4 —甲基六氫吡 畊一 1 一基磺醯基）一 2 -正丙氧苯基〕—3 -正丙基一 2，6 — 二氫一 7H —吼口坐並〔4，3 — d〕嘧π定一 7-酮 由實施例1 1 8之標題化合物依實施例1 1 6之步驟 製得，呈黃色泡沬狀（7 1 % )。 5 ( C D C 1 3 ):〇.89(3H，t)， 1 · 1 6 ( 3 Η，t )， 1 · 7 8 ( 2 Η，m )， 2 ·〇 4 ( 2 Η，m )， 2 · 2 7 ( 3 Η，s )， 2 · 4 9 ( 4 Η，m )， 2 · 9 6 ( 2 Η ， t )， (讀先閱讀背面之注意事項再填寫本頁) -S·口 本紙張尺度適用中國國家標準（CNS ) Α4規格（210X 297公釐） -170- 524805 經濟部中央標準局員工消費合作社印製 Α7 Β7 五、發明説明（168) 3.1〇(4H，m)， 4 · 2 2 ( 2 Η，t )， 6.76 (2H，d)， 7.18(lH，d)， 7.29(2H，cl)， 7*83 (lH5d)， 8 · 8 2 ( 1 H，s )， l〇.59(lH，s)。 LRMS ·ιή / z 566 (M+l)+。 實施例1 2 0 2 —（4 一甲烷磺醯胺苯基）一 5 —〔5 — (4 —甲 基六氫吡畊一 1 一基磺醯基）一 2 -正丙氧苯基〕一 3 -正丙基一 2，6 -二氫—7H —吡唑並〔4，3 - d〕嘧 陡—了 —醒 由實施例1 1 9之標題化合物及甲烷磺醯氯依實施例 1 1 7之步驟製得，呈黃色泡沬狀（5 5 % )。 元素分析實測値：C，5 3 · 0 5 ; Η，5 · 7 2 ; N， 1 4 . 94 。C3〇h39N7〇6S2; 0 · 2〇H2〇計算 値 C，53.〇8;H，5.71;N，14.84%。 5 ( C D C 1 a ):〇.97(3H，t)， 1.19(3H，t)， 1·8〇（2Η，πί)， 2·〇7(2Η，γπ)， 本紙張尺度適用中國國家標準（CMS ) Α4規格（210Χ 297公釐） -171 - (讀先閱讀背面之注意事項再填寫本頁) I衣 經濟部中央標準局員工消費合作社印製 524805 Α7 Β7 五、發明説明（169) 2 · 3 〇（3 Η，s )， 2 · 5 2 ( 4 Η，m )， 3 ·〇 2 ( 2 Η，t )， 3 · 1 6 ( 7 Η，m )， 4 · 2 8 ( 2 Η，t )， 6 · 9 〇（1 Η，d )， 7 · 1 9 ( 1 Η，d )， 7 · 4 2 ( 2 Η，d )， 7 · 5 7 ( 2 Η，d )， 7.85 (lH，d)， 8 · 8 3 ( 1 Η，s )， 10.72(lH，s)。 LRMS:m/z 644 (M+1)+。 實施例1 2 1 5 —〔5 —（4 一乙基六氫吡哄一1 一基磺醯基）一 2 —正丙氧苯基〕一 2 — (4 -硝苯基）—3 —正丙基一 2 ’ 6 —二氫一 7H —吡唑並〔4，3 - d〕嘧啶 _7 - 酮 由製備例1 2 4之標題化合物及1 -乙基六氫吡畊依 實施例1之步驟製得，呈黃色固體（82%)。 5 ( C D C 1 a ):〇.96(3H，t)， 1 · 1 6 ( 3 Η，t )， 1 · 4 2 ( 3 Η ， t )， 本紙張尺度適用中國國家標準（CNS ) Α4規格（210X297公釐）_彳72 - (請先閱讀背面之注意事項再填寫本頁)Printed by the Consumer Cooperatives of the Central Standards Bureau of the Ministry of Economic Affairs 524805 M ^ __ ϋ-V. Description of the invention (165) 5 — [5_ (4 monoethylhexahydropyridine 1 1 base sulfomethyl) — 2 to n-propoxy Phenyl] 2- (2-methanesulfonamidophenyl) -3 3-n-propyl-2,6-dihydro-7-pyrazolo [4,3-d] pyrimidin-7-one under nitrogen Methanesulfonyl chloride (0.156 m 1 '2.0 mm) was added to a mixture containing the title compound of Example 116 (583 mg, 1.0 mm) and pyridine (8 ml). In the solution, the whole solution was stirred at 50 ° C for 18 hours, and then evaporated under reduced pressure. The residue was partitioned between ethyl acetate and water, and the separated organic phase was washed with brine and dried (Na 2 S 0 4), and then evaporated under reduced pressure. The resulting brown sponge-like substance was purified on silica gel by column chromatography using a gradient of dichloromethane: methanol (100: 99 to 99: 1 to 98: 2 to 97: 3) to obtain milk. The title compound (32%) in the form of vesicles was measured by elemental analysis: c, 5 3 · 96; osmium, 6 · 0 1; N, 14 · 38. C 3OH39N7〇6S2; 0.60H2O calculation 値 C, 53.89; H, 6.06; N, 1467%. 5 (CDC 1 3): 0.91 (3H, t), 1 · 0 1 (3 Η, t), 1 · 1 9 (3 Η, t), 1. 7 5 (2 Η, m), 2 · 〇7 (2 Η, m), 2 · 4 0 (2 Η, q), 2 · 5 3 (4 Η, m), this paper size applies Chinese National Standard (CNS) A4 specification (210X297 mm) ~ "168-I (Please read the notes on the back before filling this page) Order 4 524805 Α7 Β7 V. Description of the invention (166) 2. 9 3 (2 Η, t), 3 · 07 (3 Η, s) , 3 · 09 (4 Η, m), 4. 2 9 (2 Η, t), 7 · 16 (2 Η, m), 7 · 3 5 (2 Η, m), 7 · 5 7 ( 1 Η, t), 7 · 8 2 (2 Η, d), 8 · 8 〇 (1 Η, s), 10.74 (lH, s). LRMS: m / z 658 (M + 1) + Example 1 1 8 Printed by the Consumer Cooperatives of the Central Bureau of Standards of the Ministry of Economic Affairs (please read the precautions on the back before filling out this page) 5 — [5 — (4 Methylhexyl-1 ) 2 -n-propoxyphenyl]-2-(4-nitro)-3-n-propyl-2, 6-dihydro-7H-pyrazolo [4, 3- — d] pyrimidine-7 -one Compounded from the title of Preparation Example 1 2 4 And 1-methylhexahydropyridine was prepared according to the procedure of Example 1. It was yellow foamy (63%). 5 (CDC 1 3): 0.96 (3H, t); 1 · 1 6 ( 3 Η, t), 1 · 8 0 (2 Η, m), 2 · Ο 5 (2 Η, m), 2 · 2 7 (3 Η, s), 2 · 4 9 (4 Η, m), This paper size applies to China National Standard (CNS) A4 (210X 297 mm) -169- Printed by the Consumer Cooperatives of the Central Standards Bureau of the Ministry of Economic Affairs 524805 A7 B7 V. Description of the invention (167) 3. 1 0 (6 Η, m ), 4.27 (2H, t), 7 · 1 8 (1 Η, d), 7 · 8 3 (2 Η, d), 7 · 8 6 (1 Η, d), 8 · 4 6 (2 Η, d), 8 · 84 (1 Η, s), 10.75 (1H, s). LRMS: m / z 596 (M + 1) +. Example 1 1 9 2 — (4 monoaminophenyl )-5 — [5 — (4-methylhexahydropyridine-1 1-sulfosulfanyl) —2-n-propoxyphenyl] -3—n-propyl-2,6—dihydro-7H — Oral and [4,3-d] pyridine-7-one was prepared from the title compound of Example 1 18 according to the procedure of Example 1 16 and showed a yellow foam (71%). 5 (CDC 1 3): 0.89 (3H, t), 1 · 16 (3 Η, t), 1 · 7 8 (2 Η, m), 2 · 〇 4 (2 Η, m), 2 · 2 7 (3 Η, s), 2 · 4 9 (4 Η, m), 2 · 9 6 (2 Η, t), (Read the precautions on the back before filling this page) -S · Spoken Paper size applies Chinese National Standard (CNS) A4 specification (210X 297 mm) -170- 524805 Printed by the Consumer Cooperatives of the Central Standards Bureau of the Ministry of Economic Affairs Α7 Β7 V. Description of the invention (168) 3.1〇 (4H, m), 4 · 2 2 (2 Η, t), 6.76 (2H, d), 7.18 (lH, d), 7.29 (2H, cl), 7 * 83 (lH5d), 8 · 8 2 (1 H, s), l〇 .59 (lH, s). LRMS · ιή / z 566 (M + l) +. Example 1 2 0 2 — (4-methanesulfonamidophenyl) —5— [5- (4-methylhexahydropyridine-1—1-sulfosulfanyl) —2-n-propoxyphenyl] — 3 -n-propyl-2,6-dihydro-7H-pyrazolo [4,3-d] pyrimidone-wake up from the title compound of Example 1 1 9 and methanesulfonyl chloride according to Example 1 1 It was prepared in step 7 and was yellow foamy (55%). Elemental analysis: 値: C, 5 3 · 0 5; Η, 5 · 7 2; N, 1 4. 94. C3Oh39N7O6S2; 0. 2OH2O calculation C, 53.08; H, 5.71; N, 14.84%. 5 (CDC 1 a): 0.97 (3H, t), 1.19 (3H, t), 1.8 × (2Η, πί), 2.07 (2Η, γπ), this paper standard applies Chinese national standard (CMS) Α4 specification (210 × 297 mm) -171-(Read the precautions on the back before filling out this page) I Printed by the Consumers' Cooperative of the Central Standards Bureau of the Ministry of Economic Affairs 524805 Α7 Β7 V. Description of Invention (169) 2 · 3 0 (3 Η, s), 2 · 5 2 (4 Η, m), 3 · 〇 2 (2 Η, t), 3 · 1 6 (7 Η, m), 4 · 2 8 (2 Η , T), 6 · 9〇 (1Η, d), 7 · 19 (1Η, d), 7 · 4 2 (2Η, d), 7 · 5 7 (2Η, d), 7.85 ( lH, d), 8 · 8 3 (1 Η, s), 10.72 (lH, s). LRMS: m / z 644 (M + 1) +. Example 1 2 1 5 — [5 — (4-Ethylhexahydropyridine-1—1-sulfosulfanyl) —2—n-propoxyphenyl] —2— (4-nitrophenyl) —3—n Propyl-2'6-dihydro-7H-pyrazolo [4,3-d] pyrimidin-7-one was prepared from the title compound of Preparation Example 1 2 4 and 1-ethylhexahydropyridine according to Example 1 Prepared as a yellow solid (82%). 5 (CDC 1 a): 0.96 (3H, t), 1 · 16 (3 Η, t), 1 · 4 2 (3 ，, t), this paper size applies to China National Standard (CNS) Α4 specifications (210X297mm) _ 彳 72-(Please read the notes on the back before filling this page)

、1T #, 524805 A7 B7 五、發明説明（17〇) 1 · 8 〇（2 Η，m )， 2 .〇 2 ( 2 Η，m )， 2 · 2 4 ( 2 Η，m )， 2 · 4 4 ( 4 Η，m )， 3 · 1 〇（6 Η，m )， 4 · 3 1 ( 2 Η，t )， 7 · 1 8 ( 1 Η，d )， 7 · 8 0 ( 2 Η，d )， 7 · 8 6 ( 1 Η，d )， 8.46(2H，d)， 8 · 8 8 ( 1 Η，s )， l〇.79(lH，s)。 LRMS :m/z 610 (M+l)+。 實施例1 2 2 經濟部中央標準局員工消費合作社印製 (讀先閱讀背面之注意事項再填寫本頁 2 —（4 一胺苯基）—5 —〔5 — (4 —乙基六氫吡 哄一 1 一基磺醯基）一 2 -正丙氧苯基〕一 3 -正丙基一 2，6 —二氫—7H —吡唑並〔4，3 — d〕嘧啶一7 — 酮 由實施例1 2 1之標題化合物依實施例1 1 6之步驟 製得，呈白色固體（64%)。 5 ( C D C 1 a ):〇.91(3H，t)， 1 · 1 6 ( 3 Η，t )， 1 · 4 〇（3 Η，t )， 本紙張尺度適用中國國家標準（CNS ) Α4規格（210Χ 297公釐）-1 73 - 524805 經濟部中央標準局員工消費合作社印製 A7 B7 五、發明説明（171) 1 · 8 3 ( 2 Η，m )， 2 ·〇 5 ( 2 Η，m )， 2 · 2 5 ( 2 Η，m )， 2 · 4 9 ( 4 Η，m )， 2 · 9 6 ( 2 Η，t )， 3 . 1 0 ( 4 Η，m )， 4 · 2 8 ( 2 Η，t )， 6 · 8_ 〇（2 Η，d )， 7 · 1 8 ( 1 H，d )， 7 · 3 2 ( 2 H，d )， 7 · 8 3 ( 1 H，d )， 8 · 8 6 ( 1 H，s )， l〇.64(lH，s)。 L R M S ： m / z 58〇（M+1)+。 實施例1 2 3 2— (4 —乙烷磺醯胺苯基）一5 —〔5 —（4 一乙 基六氫吡畊一 1 一基磺醯基）一 2 -正丙氧苯基〕—3-正丙基一 2，6 —二氫一 7H -吡唑並〔4，3 — d〕嘧 啶一 7 —酮 由實施例1 2 2之標題化合物及乙烷磺醯氯依實施例 1 1 7之步驟製得，呈桃色（pmk )固體（5 2 % )。 元素分析實測値：C，5 5 ·〇7 ; Η，6 · 1 8 ; N， 14 . 39 。C31H41N7〇6S2 計算値 本纸張尺度適用中國國家標準（CNS ) A4規格（210X297公釐）-174 - (請先閱讀背面之注意事項再填寫本百〇 •碰·, 1T #, 524805 A7 B7 V. Description of the invention (17〇) 1 · 8 (22, m), 2.02 (2Η, m), 2 · 2 4 (2 4, m), 2 · 4 4 (4 Η, m), 3 · 1 〇 (6 Η, m), 4 · 3 1 (2 Η, t), 7 · 1 8 (1 Η, d), 7 · 8 0 (2 Η, d), 7 · 8 6 (1 Η, d), 8.46 (2H, d), 8 · 8 8 (1 Η, s), 10.79 (1 H, s). LRMS: m / z 610 (M + 1) +. Example 1 2 2 Printed by the Consumer Cooperatives of the Central Bureau of Standards of the Ministry of Economic Affairs Coax 1 1-sulfofluorenyl) 2 -n-propoxyphenyl] 3-n-propyl-2,6-dihydro-7H-pyrazolo [4,3-d] pyrimidin-7-one The title compound of Example 1 2 1 was prepared according to the procedure of Example 1 16 as a white solid (64%). 5 (CDC 1 a): 0.91 (3H, t), 1 · 1 6 (3 Η , T), 1 · 4 0 (3 Η, t), this paper size applies Chinese National Standard (CNS) A4 specification (210 × 297 mm) -1 73-524805 Printed by A7, B7, Consumer Cooperative of Central Bureau of Standards, Ministry of Economic Affairs V. Description of the invention (171) 1 · 8 3 (2 Η, m), 2 · 05 (2 Η, m), 2 · 2 5 (2 Η, m), 2 · 4 9 (4 Η, m) , 2 · 9 6 (2 Η, t), 3. 1 0 (4 Η, m), 4 · 2 8 (2 Η, t), 6 · 8_ 〇 (2 Η, d), 7 · 1 8 ( 1 H, d), 7 · 3 2 (2 H, d), 7 · 8 3 (1 H, d), 8 · 8 6 (1 H, s), 10.64 (1 H, s). LRMS: m / z 58〇 (M + 1) +. Example 1 2 3 2 -— (4-ethanesulfonamidophenyl) —5— [5— (4-ethylhexahydropyridine—one—one] Sulfosulfonyl) -2-n-propoxyphenyl] -3-n-propyl-2,6-dihydro-7H-pyrazolo [4,3-d] pyrimidin-7-one from Example 1 2 The title compound of 2 and ethanesulfonyl chloride were prepared according to the procedures of Example 11 and showed a peach-colored (pmk) solid (52%). Elemental analysis: 値: C, 5 5 · 07; Η, 6 · 1 8; N, 14. 39. C31H41N7〇6S2 Calculate the size of this paper to apply the Chinese National Standard (CNS) A4 specification (210X297 mm) -174-(Please read the precautions on the back before filling this one hundred. ·

、-s'XJ 524805 經濟部中央標準局員工消費合作社印製 A7 B7 五、發明説明（172) C，55.42;H，6.15;N，14.59%。 5(CDCl3):〇.96(3H，t)， 1 · 1 8 ( 3 Η，t )， 1 · 4 2 ( 3 Η，t )， 1 · 7 8 ( 2 Η，m )， 2.〇2(2H，m)， 2 · 4 2 ( 2 Η，m )， 2 · 5 8 ( 4 Η，m )， 3 ·〇 2 ( 2 Η，t )， 3 · 1 6 ( 4 Η，m )， 3 · 2 〇（2 Η，m )， 4 · 2 2 ( 2 Η，t )， 7 · 1 8 ( 2 Η，d )， 7 · 4 3 ( 3 Η，m )， 7 · 8 2 ( 2 Η，d )， 8 · 8 〇（1 Η，s )， 1 〇· 7 〇（1 Η ， s )。 L R M S ： m / z 672 (M+1)+。 實施例1 2 4 5 —〔5 — (4 —乙基六氫吡畊—1—基磺醯基）一 2 -正丙氧苯基〕一 3 —正丙基—2 —〔4 一（丙一 2 — 基磺醯胺基）苯基〕一 2，6 -二氫一 7H -吡唑並〔4 ，3 — d〕嘧啶—7 —酮 本紙張尺度適用中國國家標準（CNS ) Α4規格（210X 297公釐）-175 - (請先閱讀背面之注意事項再填寫本頁), -S'XJ 524805 Printed by the Consumer Cooperatives of the Central Standards Bureau of the Ministry of Economic Affairs A7 B7 V. Description of Invention (172) C, 55.42; H, 6.15; N, 14.59%. 5 (CDCl3): 0.96 (3H, t), 1.18 (3 Η, t), 1.4.2 (3 Η, t), 1.7.8 (2 Η, m), 2. 2 (2H, m), 2 · 4 2 (2 Η, m), 2 · 5 8 (4 Η, m), 3 · 〇2 (2 Η, t), 3 · 1 6 (4 Η, m) , 3 · 2 0 (2 Η, m), 4 · 2 2 (2 Η, t), 7 · 1 8 (2 Η, d), 7 · 4 3 (3 Η, m), 7 · 8 2 ( 2Η, d), 8.8 8 (1Η, s), 10.7 （(1Η, s). L R M S: m / z 672 (M + 1) +. Example 1 2 4 5 — [5 — (4-ethylhexahydropyridyl-1-ylsulfonyl) —2-n-propoxyphenyl] —3—n-propyl-2— [4— (propyl -2-Sulfosulfonylamino) phenyl] -2,6-dihydro-7H-pyrazolo [4,3-d] pyrimidin-7-one This paper is sized to the Chinese National Standard (CNS) A4 specification ( 210X 297mm) -175-(Please read the notes on the back before filling this page)

、1T 524805 Α7 Β7 五、發明説明（173) 由實施例1 2 2之標題化合物及2 -丙烷磺醯氯依實 施例1 1 7之步驟製得，呈固體（2 8 % )。 元素分析實測値：C，5 3 . 5 9 ; Η，6 . 1 5 ; N， 13 · 34 。 C32H43N7〇6S2;〇· 17H2〇計算 値 C，53.64;H，6.53;N，13.68%。 5 ( C D C 1 a ):〇.92(3H，t)； 1 · Ο 3 ( 3 Η，t )， 1 · 1 8 ( 3 Η，t )， 1 · 4 2 ( 6 Η，m )， 1 · 7 8 ( 2 Η，m )， 2 · Ο 7 ( 2 Η，m )， 2 · 3 8 ( 2 Η，t )， 2 · 5 7 ( 4 Η，m )， 3 · Ο 2 ( 2 Η，t )， 3 · 1 6 ( 4 Η，m )， 3 · 3 8 ( 1 Η，m )， (讀先閲讀背面之注意事項再填寫本頁) 衣· 、1Τ 經濟部中央標準局員工消費合作社印製 4 · 2 2 ( 2 Η ，t )， 7 . 1 8 ( 2 Η ，d )， 7 · 4 5 ( 3 Η ’ m )， 7 . 8 〇 ( 2 Η ，d )， 8 · 8 〇 ( 1 Η ，s )， 1〇 7 1 ( 1 H ， s ) LRMS .in / ζ 686 (Μ+1)+。 本纸張尺度適用中國國家標準（CNS ) Α4規格（210X297公釐）-176 - 524805 A7 B7 五、發明説明（174) 實施例1 2 5 5 —〔5 —（4 一甲基六氫吡哄一 1 一基磺醯基）一 2 -正丙氧苯基〕一 3 —正丙基—2 —嘧啶一 2 —基一 2 ，6 —二氫—7H —吡唑並〔4，3 — d〕嘧啶一7 —酮 由製備例1 2 5之標題化合物及1 -甲基六氫吡哄依 實施例1之步驟製得，呈白色泡沬狀（4 0 % )。 (5(CDCl3):l.〇〇（3H，t)， 1 · 1 8 ( 3 Η，t )， 1 · 8 0 ( 2 Η ，m )， (請先閱讀背面之注意事項再填寫本頁) «衣_ 經濟部中央標準局員工消費合作社印製1T 524805 A7 B7 V. Description of the invention (173) It was prepared from the title compound of Example 1 2 2 and 2-propanesulfonyl chloride in accordance with the procedure of Example 1 17 as a solid (28%). Elemental analysis: 値: C, 5 3. 5 9; Η, 6. 1 5; N, 13 · 34. C32H43N7〇6S2; 〇17H2〇 calculation 2 C, 53.64; H, 6.53; N, 13.68%. 5 (CDC 1 a): 0.92 (3H, t); 1 · Ο 3 (3 Η, t), 1 · 1 8 (3 Η, t), 1 · 4 2 (6 Η, m), 1 · 7 8 (2 Η, m), 2 · 〇 7 (2 Η, m), 2 · 3 8 (2 Η, t), 2 · 5 7 (4 Η, m), 3 · Ο 2 (2 Η , T), 3 · 1 6 (4 Η, m), 3 · 3 8 (1 Η, m), (read the precautions on the back before filling this page) Clothing ·, 1T Employees of the Central Standards Bureau of the Ministry of Economic Affairs Cooperative prints 4 · 2 2 (2 Η, t), 7. 1 8 (2 Η, d), 7 · 4 5 (3 Η 'm), 7.8 〇 (2 Η, d), 8 · 8 〇 (1Η, s), 107 (1H, s) LRMS.in/ζ 686 (M + 1) +. This paper size applies Chinese National Standard (CNS) A4 specification (210X297 mm) -176-524805 A7 B7 V. Description of the invention (174) Example 1 2 5 5 — [5 — (4 monomethylhexahydropyridine) -1-1-sulfofluorenyl)-2-n-propoxyphenyl]-3-n-propyl-2-pyrimidine-2-2-2, 6-dihydro-7H-pyrazolo [4, 3 — d ] Pyrimidine-7-one was prepared from the title compound of Preparation Example 1 2 and 1-methylhexahydropyridine according to the procedure of Example 1, and was white foamy (40%). (5 (CDCl3): 1.0 (3H, t), 1 · 1 8 (3 Η, t), 1 · 8 0 (2 Η, m), (Please read the notes on the back before filling this page ) «Clothes _ Printed by the Consumer Cooperatives of the Central Bureau of Standards of the Ministry of Economic Affairs

680366805827s 02514214889 M ··········* cw 2 22334777881L680366805827s 02514214889 M ..... cw 2 22334777881L

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、1T 6 2 T—I例施 本紙張尺度適用中國國家標準（CNS ) Α4規格（210X 297公釐）-1 77 - 524805 A7 B7 五、發明説明（175) 經濟部中央標準局員工消費合作社印製 2 — 環 丁 基 甲 基 — 5 — C 2 — 乙 氧 — 5 — ( 4 — 甲 基 -JL- 氫 吡 畊 — 1 — 基 磺 醯 基 ) 苯 基 ) — 3 — 正 丙 基 — 2 y 6 — 二 氫 — 7 Η — 吡 唑 並 [ 4 5 3 — d ) 喃 啶 — 7 — 酮 由 製 備 例 1 2 6 之 標 題 化 合 物 及 1 — 甲 基 _L^ 氫 吡 畊 依 實 施 例 1 之 步 驟 製 得 ， 呈 白 色 固 體 ( 8 4 % ) 〇 5 ( C D C 1 3 , ) ·· 1 •〇： 1 ( 3 Η > t ) 1 • 6 〇 ( 3 Η ? t ) 5 1 • 8 8 ( 6 Η 5 m ) ? 2 • 〇 8 ( 2 Η ? m ) 1 2 * 3 〇 ( 3 Η 5 s ) 5 2 • 5 2 ( 4 Η m ) ， 2 • 9 8 ( 3 Η m ) 5 3 • 1 2 ( 4 Η m ) 4 • 3 3 ( 4 Η m ) 7 • 1 5 ( 1 Η d ) y 7 • 8 1 ( 1 Η 5 d ) 5 8 • 7 9 ( 1 Η 5 s ) ? 1 〇 • 5 4 ( 1 Η y S ) 〇 L R Μ S • m / z 5 2 9 ( Μ + 1 ) + 〇 實 施 例 1 2 7 2 — 環 丁 基 甲 基 — 5 — [ 5 — ( 4 — 甲 基 r i 氫 吡 哄 — 1 — 基 磺 醯 基 ) — 2 — 正 丙 氧 苯 基 ] — 3 — 正 丙 基 — 2 5 6 — 二 氫 — 7 Η — 吡 口坐 並 [ 4 5 3 — d ) 嚼 啶 — 7 酮 本紙張尺度適用中國國家標準（CNS ) Α4規格（210X297公釐）-1 78 - (請先閱讀背面之注意事項再填寫本頁) 衣·1. 1T 6 2 T—I. The paper size is applicable to the Chinese National Standard (CNS) A4 specification (210X 297 mm) -1 77-524805 A7 B7 V. Description of the invention (175) Printed by the Consumers' Cooperative of the Central Standards Bureau of the Ministry of Economic Affairs Preparation 2 — cyclobutylmethyl — 5 — C 2 — ethoxy — 5 — (4 —methyl-JL-hyperpyrazine — 1 — sulfosulfanyl) phenyl) — 3 — n-propyl — 2 y 6 — Dihydro-7 pyrene-pyrazolo [4 5 3 — d) uridine-7-one was prepared from the title compound of Preparation Example 1 2 6 and 1-methyl_L ^ Hydropyrine according to the procedure of Example 1 , As a white solid (84%) 〇5 (CDC 1 3,) ·· 1 • 〇: 1 (3 Η > t) 1 • 6 〇 (3 Η? T) 5 1 • 8 8 (6 Η 5 m)? 2 • 〇8 (2 Η? m) 1 2 * 3 〇 (3 Η 5 s) 5 2 • 5 2 (4 Η m), 2 • 9 8 (3 Η m) 5 3 • 1 2 ( 4 Η m) 4 • 3 3 (4 Η m) 7 • 1 5 (1 Η d) y 7 • 8 1 (1 Η 5 d) 5 8 • 7 9 (1 Η 5 s)? 1 〇 • 5 4 (1 Η y S) 〇LR Μ S • m / z 5 2 9 (Μ + 1) + 〇 Example 1 2 7 2 — Cyclobutylmethyl — 5 — [5 — (4-methylri Hydropyridine — 1 — sulfosulfanyl) — 2 — n-propoxyphenyl] — 3 — n-propyl — 2 5 6 — dihydro — 7 hydrazine — pyrazoline and [4 5 3 — d) pyridin — 7 ketones The paper size applies to Chinese National Standard (CNS) A4 specifications (210X297 mm)- 1 78-(Please read the notes on the back before filling this page)

、1T 524805 A7 B7 五、發明説明（176) 經濟部中央標隼局員工消費合作社印製 由 製 備 例 1 2 7 之 標題 化 合 物及 1 -甲 1基六 氫吡畊依 實 施 例 1 之 步 驟 製 得 > 呈白 色 泡 沬狀 ( 5 6 % ) 〇 元 素 分 析 實 測 値 C 5 5 9 • 2 4 ； Η ，7 •〇 1 ; N， 1 5 參 2 4 〇 C 2 r 7 H 3 8 N 6〇 4 S計 算 値 C > 5 9 • 7 6 y H ， 7 · 〇 6 ；Ν j 15 • 4 4 %。 5 ( C D C 1 3 : ) 1 •〇 4 ( 3 Η ， t ) 1 • 1 2 ( 3 Η 5 t ) 1 • 9 〇 ( 6 Η ? m ) 2 • 〇 6 ( 4 Η 5 m ) > 2 • 3 〇 ( 3 Η J s ) 2 • 5 〇 ( 4 Η J m ) j 2 參 9 8 ( 3 Η 5 m ) 3 • 1 2 ( 4 Η 5 m ) 5 4 • 2 2 ( 2 Η 5 t ) 4 • 3 〇 ( 2 Η y d ) > 7 • 1 4 ( 1 Η j d ) ， 7 • 8 〇 ( 1 Η d ) ， 8 • 7 8 ( 1 Η 5 s ) 1 〇 • 5 4 ( 1 H s )° L R Μ S : m / z 5 4 3 ( Μ + 1. ) + 〇 實 施 例 1 2 8 5 一 [ 5 — ( 4 — 甲基 六 氫 吡哄 一 1 - 基磺 醯基）一 2 — 正 丙 氧 苯 基 ] — 2 -( 1 — oxido 〇比 U定 一 2 - -基）甲基 本紙張尺度適用中國國家標準（CNS ) Α4規格（210X 297公釐）-1 79 - (讀先閲讀背面之注意事項再填寫本頁)1T 524805 A7 B7 V. Description of the invention (176) Printed by the Consumer Cooperative of the Central Bureau of Standards, Ministry of Economic Affairs, prepared from the title compound of Preparation Example 1 2 7 and 1-methyl-1-hexahydropyridine according to the procedure of Example 1. > White foam (56%) 〇 Elemental analysis: 値 C 5 5 9 • 2 4; Η, 7 • 〇1; N, 15 reference 2 4 〇C 2 r 7 H 3 8 N 6〇 4 S calculation 値 C > 5 9 • 7 6 y H, 7 · 〇 6; Ν j 15 • 4 4%. 5 (CDC 1 3:) 1 • 〇4 (3 Η, t) 1 • 1 2 (3 Η 5 t) 1 • 9 〇 (6 Η? M) 2 • 〇6 (4 Η 5 m) > 2 • 3 〇 (3 Η J s) 2 • 5 〇 (4 Η J m) j 2 See 9 8 (3 Η 5 m) 3 • 1 2 (4 Η 5 m) 5 4 • 2 2 (2 Η 5 t ) 4 • 3 〇 (2 Η yd) > 7 • 1 4 (1 Η jd), 7 • 8 〇 (1 Η d), 8 • 7 8 (1 Η 5 s) 1 〇 • 5 4 (1 H s) ° LR Μ S: m / z 5 4 3 (Μ + 1.) + 〇 Example 1 2 8 5-[5 — (4 —methylhexahydropyridine — 1-sulfosulfanyl) — 2 — N-propoxyphenyl] — 2-(1 — oxido 〇 than U 2-2--yl) methyl This paper size applies to Chinese National Standard (CNS) A4 specification (210X 297 mm) -1 79-(read first (Read the notes on the back and fill out this page)

、1T #, 經濟部中央標準局員工消費合作社印製 524805 Α7 Β7 五、發明説明（177) —3 —正丙基—2，6 —二氫—7H -吡唑並〔4，3 -d〕嘧啶一 7 -酮 在氮氣下將3 —氯過氧苄酸（50 — 55%; 152 mg，〇 · 44mmo 1 )加入一攪拌中而含有實施例6 標題化合物（l〇8mg ，〇· 19mmo 1)及二氯甲 烷（5 m 1 )之溶液裡，並持續攪拌1 8小時。反應混合 物以二氯甲烷（2 0 m 1 )稀釋，再依續以5 %偏二亞硫 酸鈉水溶液（2 0 m 1 ) ，1 〇 %碳酸鉀水溶液（2 0 m 1 )及鹽水（1 5 m 1 )洗之，再經乾燥（N a 2 S〇4 )後減壓蒸發。得到的黃色泡沬狀物質以管柱層析法利用 二氯甲烷：甲醇：〇·880氨水（100:1:1至 1〇0 : 3 : 1 )之沖提梯度在矽膠上純化而得到呈橙色 固體之標題化合物（36mg)。 5(CDCl3):l.〇〇（3H，t)， 1 · 1 5 ( 3 Η，t )， 1 · 7 9 ( 2 Η，m )， 2 ·〇 7 ( 2 Η，m )， 2 · 2 8 ( 3 Η，m )， 2.48(4H，m)， 3 · 0 0 ( 2 Η，t )， 3.12(4H，m)， 4 · 2 7 ( 2 Η，t ).， 5 · 8 2 ( 2 Η，s )， 6 · 7 9 ( 1 Η，d )， 本紙張尺度適用中國國家標準（CNS ) Α4規格（210Χ 297公釐） -180- (請先閲讀背面之注意事項再填寫本頁) φ 訂 524805 經濟部中央標隼局員工消費合作社印製 A7 B7 五、發明説明（178) 7 · 2 2 ( 3 Η，m )， 7 · 8 5 ( 1 Η，d )， 8 · 3 〇（1 Η，d )， 8 · 8 〇（1 Η，s )， 10.66(lH，s)。 LRMS:m/z 582 (M+1)+。 實施例1 2 9 5 —〔5 —（4 —乙基六氫吡畊一 1 一基磺醯基）— 2 -正丙氧苯基〕一 2 —（1 一氧吼卩定一 2 —基）曱基— 3 —正丙基一 2，6 —二氫—7H —吡唑並〔4，3-d 〕嘧啶一 7 —酮 由實施例1 2之標題化合物依實施例1 2 8之步驟而 製得，呈黃色泡沫狀（6 3 % )。 元素分析實測値：C，5 7 · 0 4 ; Η，6 . 1 4 ; N， 15 · 80。C29H37N7〇5S ； 0 . 2 5 C Η 2 C 1 2 計算値C，56.95;H，6.13;N， 15.89 %。 (5(CDCl3) :〇.99(6H，m)， 1 · 1 9 ( 3 Η，t )， 1 · 8 〇（2 Η，m )， 2 · 0 2 ( 2 Η，m )， 2 · 4 1 ( 2 Η，q )， 2 · 5 2 ( 4 Η ，m )， 本纸張尺度適用中國國家標準（CNS ) A4規格（210X297公釐）-181 - (請先閱讀背面之注意事項再填寫本頁), 1T #, printed by the Consumer Cooperatives of the Central Standards Bureau of the Ministry of Economic Affairs 524805 Α7 Β7 V. Description of the invention (177) —3 —n-propyl-2,6 —dihydro-7H-pyrazolo [4,3 -d] Pyrimidine-7-one was added with 3-chloroperoxybenzoic acid (50-55%; 152 mg, 0.44 mmo 1) under nitrogen to agitate to contain the title compound of Example 6 (108 mg, 0.19 mmo 1). ) And dichloromethane (5 m 1), and stirring was continued for 18 hours. The reaction mixture was diluted with dichloromethane (20 m 1), and then successively with a 5% sodium metabisulfite aqueous solution (20 m 1), a 10% potassium carbonate aqueous solution (20 m 1), and a brine (15 m 1 ) Washed, and then dried (N a 2 S04) and evaporated under reduced pressure. The obtained yellow foamy substance was purified on silica gel by column chromatography using a gradient of dichloromethane: methanol: 0.8880 ammonia (100: 1: 1 to 100: 3: 1) to obtain The title compound (36 mg) as an orange solid. 5 (CDCl3): 1.0 (3H, t), 1 · 15 (3 Η, t), 1 · 7 9 (2 Η, m), 2 · 〇7 (2 2, m), 2 · 2 8 (3 Η, m), 2.48 (4H, m), 3 · 0 0 (2 Η, t), 3.12 (4H, m), 4 · 2 7 (2 Η, t)., 5 · 8 2 (2 Η, s), 6 · 7 9 (1 Η, d), this paper size applies to China National Standard (CNS) Α4 specification (210 × 297 mm) -180- (Please read the precautions on the back before filling in this Page) φ Order 524805 Printed by the Consumer Cooperatives of the Central Bureau of Standards of the Ministry of Economic Affairs A7 B7 V. Description of the invention (178) 7 · 2 2 (3 Η, m), 7 · 8 5 (1 Η, d), 8 · 3 〇 (1 Η, d), 8.8 (1 Η, s), 10.66 (lH, s). LRMS: m / z 582 (M + 1) +. Example 1 2 9 5 — [5 — (4-ethylhexahydropyridine-1 1-sulfofluorenyl) -2- 2-n-propoxyphenyl] -2— (1 ) Amidino-3 -n-propyl-2,6-dihydro-7H-pyrazolo [4,3-d] pyrimidin-7-one From the title compound of Example 12 according to the procedure of Examples 1 2 8 And it was obtained as yellow foam (63%). Elemental analysis of plutonium: C, 5 7 · 0 4; Plutonium, 6. 1 4; N, 15 · 80. C29H37N7〇5S; 0.25 C Η 2 C 1 2 Calculate 値 C, 56.95; H, 6.13; N, 15.89%. (5 (CDCl3): 0.99 (6H, m), 1 · 19 (3 Η, t), 1 · 8 〇 (2 Η, m), 2 · 0 2 (2 Η, m), 2 · 4 1 (2 Η, q), 2 · 5 2 (4 Η, m), this paper size applies Chinese National Standard (CNS) A4 specification (210X297 mm) -181-(Please read the precautions on the back before (Fill in this page)

經濟部中央標準局員工消費合作社印製 524805 Α7 Β7 五、發明説明（179) 3 ·〇 1 ( 2 Η，t )， 3 · Ο 9 ( 4 Η，m )， 4 · 2 6 ( 2 Η，t )， 5 · 8 〇（2 Η，s )， 6 · 8 9 ( 1 Η，d )， 7 · 2 〇（3 Η，m )， 7 · 8 3 ( 1 Η，d )， 8 · 2 8 ( 1 Η，d )， 8.8〇（lH，s)， * 11.63(lH，s)° LRMS:m/z 596 (M+1)+。 實施例1 3〇 3 —乙基一5 —〔2 — (2 —甲氧乙氧）一5 — (4 一甲基六氫吡畊一 1 一基磺醯基）苯基〕一 2 —（吡啶一 2 —基）甲基一 2，6 —二氫一7H —吡唑並〔4，3 — d〕嘧啶一 7 —酮 由製備例1 3 3之標題化合物及1 -甲基六氫吡畊依 實施例1之步驟製得，呈白色泡沬狀（8 5 % )。 元素分析實測値·· C，5 5 · 8 2 ; Η，5 . 8 4 ; N， 16 · 54 。C27H33N7〇5S ；〇.75H2〇計算値 C，55.8〇；H，5.98;N，16.87%。 5(CDCl3)：1.30(3H^t)^ 2 · 2 6 ( 3 Η ， s )， 本紙張尺度適用中國國家標準（CNS ) Α4規格（210Χ 297公釐）-1 82 - (請先閲讀背面之注意事項再填寫本頁)Printed by the Consumer Cooperatives of the Central Bureau of Standards of the Ministry of Economic Affairs 524805 Α7 Β7 V. Description of the invention (179) 3 · 〇1 (2 Η, t), 3 · Ο 9 (4 Η, m), 4 · 2 6 (2 Η, t), 5 · 8 〇 (2 Η, s), 6 · 8 9 (1 Η, d), 7 · 2 〇 (3 Η, m), 7 · 8 3 (1 Η, d), 8 · 2 8 (1 mm, d), 8.8 (lH, s), * 11.63 (lH, s) ° LRMS: m / z 596 (M + 1) +. Example 1 3〇3-Ethyl-5— [2- (2-methoxyethoxy) -5— (4-methylhexahydropyridine-1 1-sulfosulfanyl) phenyl] -2— ( Pyridinyl 2-yl) methyl-2,6-dihydro-7H-pyrazolo [4,3-d] pyrimidin-7-one was prepared from the title compound of Preparation Example 1 3 and 1-methylhexahydropyridine It was prepared according to the procedure of Example 1 and was white foamy (85%). Elemental analysis measured 値 ·· C, 5 5 · 8 2; Η, 5. 8 4; N, 16 · 54. C27H33N7〇5S; 0.75H2O calculated C, 55.8; H, 5.98; N, 16.87%. 5 (CDCl3): 1.30 (3H ^ t) ^ 2 · 2 6 (3 ，, s), this paper size applies to China National Standard (CNS) Α4 specification (210 × 297 mm) -1 82-(Please read the back first (Notes for filling in this page)

、1T 經濟部中央標隼局員工消費合作社印製 524805 A7 B7 五、發明説明（18〇) 2 · 4 8 ( 4 Η，m )， 3 ·〇 1 ( 2 Η，q )， 3 . 1 〇（4 Η，m )， 3 · 5 8 ( 3 Η，s )， 3 · 8 7 ( 2 Η，t )， 4 · 4 2· ( 2 Η，t )， 5 · 6 7 ( 2 Η，s )， 7.〇7(lH，d)， 7 · 1 4 ( 1 Η，d )， 7.2〇（lH，m)， 7 · 6 1 ( 1 Η，m )， 7 · 8 1 ( 1 Η，d )， 8 · 5 7 ( 1 Η，d )， 8 . 7 〇（1 Η，s )， l〇.86(lH，s)° LRMS,:m/z 569 (M+2)+。 實施例1 3 1 3 —乙基一5 —〔5 — (4 —乙基六氫吡哄一 1—基 磺醯基）一2 —（2 —甲氧乙氧）苯基〕一2 —（吡啶一 2 —基）甲基一 2 ，6 —二氫一7H —吡唑並〔4，3 — d〕嘧啶一 7 -酮 由製備例1 3 3之標題化合物及1 一乙基六氫吡畊依 實施例1之步驟製得，呈白色泡沬狀（7 3 % )。 本纸張尺度適用中國國家標準（CNS ) A4規格（210X297公釐）-1 83 - (請先閱讀背面之注意事項再填寫本頁) 4 、\呑 524805 A7 B7 五、發明説明（181) 元素分析實測値：C，5 7 · 0 8 ; Η，6 · 0 4 ; N， 16 · 51 。C28H35N7〇5S ；〇.5〇H2〇計算値 經濟部中央標準局員工消費合作社印製Printed by the Consumer Cooperative of the Central Bureau of Standards of the Ministry of Economic Affairs, 1T 524805 A7 B7 V. Description of the invention (18〇) 2 · 4 8 (4 Η, m), 3 · 〇1 (2 Η, q), 3. 1 〇 (4 Η, m), 3 · 5 8 (3 Η, s), 3 · 8 7 (2 Η, t), 4 · 4 2 · (2 Η, t), 5 · 6 7 (2 Η, s ), 7.〇7 (lH, d), 7.14 (1 1, d), 7.2〇 (lH, m), 7.6.1 (1Η, m), 7.8.1 (1Η, d), 8.57 (1 Η, d), 8.7 (1 Η, s), 10.86 (lH, s) ° LRMS, m / z 569 (M + 2) +. Example 1 3 1 3 -Ethyl-5-[5-(4-Ethylhexahydropyridine) 1-(Sulfosulfenyl)-2-(2-methoxyethoxy) phenyl] -2-( Pyridin-2-yl) methyl-2,6-dihydro-7H-pyrazolo [4,3-d] pyrimidin-7-one was prepared from the title compound of Preparation Example 1 3 and 1-ethylhexahydropyridine It was prepared according to the procedure of Example 1 and was white foamy (73%). This paper size applies to Chinese National Standard (CNS) A4 specification (210X297 mm) -1 83-(Please read the precautions on the back before filling out this page) 4, \ 呑 524805 A7 B7 V. Description of the invention (181) Element Analyze and measure 値: C, 5 7 · 0 8; Η, 6 · 0 4; N, 16 · 51. C28H35N7〇5S; 0.50H2〇 calculation 印 Printed by the Consumer Cooperative of the Central Standards Bureau of the Ministry of Economic Affairs

〇 2 C ， \)y Ν)/ XMy \ly \ί/ SMy \My \ly N)/ \)y \)/ \)y \)y N)/ s L〇 「1 H tQmQmsttsddmmdds， • > ，，，，，，，，，，，，，，，， 「I...一 3 3HHHHHHHHHHHHHHHH1/ 913242432221111111( m • c ,、 /^V Γ\ /(\ /i\ /' /l\ \' Γ\ Γν Γν /(V /IV Γν /IV /IV ·. 6D〇 9310971885 〇12708s 5C 3350158460126857 M， /~\················ cul**v^ C512233334577777881L % 〇 6 6 例 備 製 Η 3 + Μ 餐—(讀先閱讀背面之注意事項再填寫本頁〇2 C, \) y Ν) / XMy \ ly \ ί / SMy \ My \ ly N) / \) y \) / \) y \) y N) / s L〇 「1 H tQmQmsttsddmmdds, • > ,,,,,,,,,,,,,,,,,, "I ... a 3 3HHHHHHHHHHHHHHHHH1 / 913242432221111111 (m • c ,, / ^ V Γ \ / (\ / i \ / '/ l \ \' Γ \ Γν Γν / (V / IV Γν / IV / IV ·. 6D〇9310971885 〇12708s 5C 3350158460126857 M, / ~ \ ··········· cul ** v ^ C512233334577777881L % 〇6 6 cases of prepared Η 3 + Μ meals— (Read the precautions on the back before filling in this page

、1T 本紙張尺度適用中國國家標準（CNS ) A4規格（210X 297公釐）-184 - 524805 經濟部中央標準局員工消費合作社印製 A7 B7五、發明説明（彳82) 3 —乙基—1 Η —吡唑一5 —羧酸乙酯 在氮氣下將乙氧化鈉的乙醇溶液（2 1 % w/w ; 1 4 3 m 1 ，〇 · 3 9 m ο 1 )逐滴加入一攪拌中且以冰 冷卻之含有草酸二乙酯（59 · 8ml ，〇 · 44m〇1 )及絕對乙醇（2 0 0 m 1 )之溶液裡，再將整個溶液攪 拌1 5分鐘。接著逐滴添加2 — 丁酮（butan-2-one)( 3 9 m 1 ，〇 · 4 4 m ο 1 )，移開冷卻浴，再於室溫下 攪拌反應混合物1 8小時，復於4 0 °C攪拌6小時，然後 再將冷卻浴移回。接著把冰醋酸（2 5 m 1 ，〇 . 4 4 m ο 1 )逐滴加入，於〇 t：下攪拌整個溶液3 0分鐘，再 逐滴添加肼水合物（20ml ，0 · 44mo 1)，令反 應混合物回到室溫，然後維持1 8小時才減壓蒸發。令殘 餘物於二氯甲烷（3 0 0 m 1 )和水（1 0 0 m 1 )之間 分配，有機相分出來後用水（2 X 1 0 0 m 1 )洗過，經 乾燥（N a 2 S 0 4 )後減壓濃縮而得到標題化合物（ 6 6 ·〇 g )。 5 ( C D C 1 a ) :l.〇4(3H，t)， 1 · 1 6 ( 3 Η，t )， 2.7〇（2H，q)， 4 · 3 6 ( 2 Η，q )， 6 · 6 〇（1 Η，s )。 L R M S ： m / z 169(M+1)+。 製備例2 (請先閱讀背面之注意事項再填寫本頁) ;φ' 、\呑 本紙張尺度適用中國國家標準（ CNS ) A4規格（210X 297公釐）_ 185 - 524805 A.7 B7 五、發明説明（183) 3 —乙基一 1 Η —吡唑一 5 —羧酸 將氫氧化鈉水溶液（1 0 Μ ·’ 1 0 0 m 1 ，1 ·〇 m ◦ 1 )逐滴加入一攪拌中製備例1標題化合物（ 6 6 · 0 g，0 · 3 9 m ο 1 )的甲醇懸浮液裡’把所得 溶液加熱迴流4小時。令冷卻的反應混合物減壓濃縮至大 約2 0 0 m 1 ，以水（2 0 〇 m 1 )稀釋後，將此混合物 用甲苯（3 X 1 〇 〇 m 1 )洗過。得到的水相部份以濃氫 氯酸酸化至P Η 4，白色沈澱物收集並抽氣乾燥而得到標 題化合物（3 4 · 1 g )。 5(DMS〇d6):l.l3(3H，t)， 2 · 5 6 ( 2 Η，Q )， 6 · 4 2 ( 1 Η，s )。 製備例3 4 —硝基一 3 -正丙基—1 Η —吡唑—5 —羧酸 把發煙硫酸（1 7 · 8 m 1 )逐滴加入攪拌中而以冰 經濟部中央標準局員工消費合作社印製 冷卻的發煙硝酸（1 6 · 0 m 1 )裡，將整個溶液加熱至 5 0 °C，然後在3 0分鐘的時間裡分批添加3 -正丙基-1 Η —吡唑—5 —羧酸（Chem. Pham. Bull·，1 984，11， 1 5 68; 16.4g，0.106mol )，同時維持反應溫度低於6 0 °C。 將所得溶液於6 0 °C加熱1 8小時，經冷卻後倒在冰上。 把白色沈澱物收集後用水洗過，再抽氣乾燥而得到標題化 合物（1 5 · 4 g )。 m· ρ_· 17 0 — 172〇C。 -186- (請先閱讀背面之注意事項再填寫本頁) 本紙張尺度適用中國國家標準（CNS ) A4規格（210X297公楚） 524805 A7 B7 五、發明説明（184) 元素分析實測値：C，4 2 · 3 5 ; Η，4 · 5 6 ; N， 21 · 07。C7H9N3〇4計算値 c，42 · 21 ; Η 4·55;Ν，21·1〇％。 5(DMS〇d6):0.90(3H，t)， 1 · 6 4 ( 2 Η，m )， 2 · 8 3 ( 2 Η，m )， 14.00(lH，s)。 製備例4 3 —乙基一 4 一硝基一 1 Η〜d比d坐—5 —竣酸 由製備例2之標題化合物依製備例3之類似方式製得 ，呈棕色固體（64%)。 δ ( D M S 0 d 6 ) :1.18(3H，t)， 2 · 8 4 ( 2 Η，m )， 13.72(lH，s)。 製備例5 經濟部中央標準局員工消費合作社印^ (請先閱讀背面之注意事項再填寫本頁) 4 一硝基—3 -正丙基一 1 H — d比π坐—5 —甲醢胺 將製備例3之標題化合物（1 5 · 4 g，0 . 0 7 7 m ο 1 )於硫醯氯（7 5 m 1 )中所形成的溶液加熱迴流 3小時，然後把冷卻的反應混合物減壓蒸發後令殘餘物與 四氫呋喃（2 X 5 0 m 1 )共沸，接著懸浮液在四氫呋喃 (5 0 m 1 )裡，擾伴的懸浮液用冰冷卻，再用氨氣處理 1小時。加水（5 0 m 1 )，再將所得混合物減壓蒸發而 本紙張尺度適用中國國家標準（CNS ) A4規格（210X297公釐）-1 87 - 5248〇5 ¾濟部中央榡準局員工消費合作社印製 A7 B7 五、發明説明（185) 得一固體，此固體經用水碾製並抽氣乾燥後即得標題化合 物（1 4 · 3 g )。 199 t：。 元素分析實測値·· C，，4 2 · 3 5 ; Η，5 · 0 7 ; N， 2 8 · 38。C7H1〇N4〇3 計算値 C，4 2 · 42 ； Η ’5·〇9;Ν，28·27%。 占（DMS〇d6):0.9〇（3H，t)， 1.68(2H，m)， 2 · 8 6 ( 2 Η，t )， 7 . 6 8 ( 1 Η，s )， 8 ·〇 〇 ( 1 Η，s )。 製備例6 3 —乙基一 4 —硝基—1 Η —吡唑一5 —甲醯胺. 由製備例4之標題化合物依製備例5之類似方式製得 ’呈白色固體（90%)。 d(DMS〇d6):1.17(3H，t)， 2 . 8 7 ( 2 Η，m )， 7.4〇(1H，s)， 7 · 6 〇 ( 1 Η，s )， 7 · 9 〇 ( 1 Η，s )。 L R M S ： m / z 185(M+1)+。 製備例7 本紙張尺度適用中國國家標準（CNS ) A4規格（210X 297公釐）-188- (讀先閱讀背面之注意事項再填寫本頁)、 1T This paper size is applicable to Chinese National Standard (CNS) A4 specification (210X 297 mm) -184-524805 Printed by the Consumers Cooperative of the Central Standards Bureau of the Ministry of Economic Affairs A7 B7 5. Invention Description (发明 82) 3 —Ethyl-1 Η—pyrazole-5—carboxylic acid ethyl ester Under nitrogen, an ethanol solution of sodium ethoxide (21% w / w; 413 m 1, 0.39 m ο 1) was added dropwise to a stirring and In an ice-cooled solution containing diethyl oxalate (59.8 ml, 0.44 mmol) and absolute ethanol (200 ml), the whole solution was stirred for 15 minutes. Then, 2-butan-2-one (39 m 1, 0.4 4 m ο 1) was added dropwise, the cooling bath was removed, and the reaction mixture was stirred at room temperature for 18 hours. Stir at 0 ° C for 6 hours, then move the cooling bath back. Then add glacial acetic acid (2.5 m 1, 0.4 4 m ο 1) dropwise, stir the entire solution at 0 t: 30 minutes, and then add hydrazine hydrate (20 ml, 0.44 mo 1) dropwise, The reaction mixture was allowed to return to room temperature and then maintained for 18 hours before evaporating under reduced pressure. The residue was partitioned between dichloromethane (300 m 1) and water (100 m 1). The organic phase was separated, washed with water (2 X 100 m 1), and dried (N a 2 S 0 4), and then concentrated under reduced pressure to obtain the title compound (66 · 0 g). 5 (CDC 1 a): 1.04 (3H, t), 1 · 16 (3Η, t), 2.7〇 (2H, q), 4 · 3 6 (2Η, q), 6 · 6 〇 (1 Η, s). L R M S: m / z 169 (M + 1) +. Preparation Example 2 (Please read the precautions on the back before filling this page); φ ', \ 呑 This paper size is applicable to China National Standard (CNS) A4 specification (210X 297 mm) _ 185-524805 A.7 B7 V. Description of the Invention (183) 3-Ethyl-1, 1-pyrazole-5, carboxylic acid Sodium hydroxide aqueous solution (10 M · '100 m 1, 1.0 m ◦ 1) was added dropwise to a stirring In a methanol suspension of the title compound of Production Example 1 (66 · 0 g, 0.39 m ο 1), the resulting solution was heated under reflux for 4 hours. The cooled reaction mixture was concentrated under reduced pressure to about 2000 m 1, diluted with water (200 m 1), and the mixture was washed with toluene (3 × 100 m 1). The obtained aqueous phase was acidified with concentrated hydrochloric acid to PΗ4, and the white precipitate was collected and dried under suction to obtain the title compound (3 4 · 1 g). 5 (DMSOd6): 1.13 (3H, t), 2.55 (2H, Q), 64.2 (1H, s). Preparation Example 3 4—Nitro-3—n-propyl—1 —pyrazole—5—carboxylic acid Dropwise added fuming sulfuric acid (17.8 m 1) to the stirring solution. The consumer cooperative printed the cooled fuming nitric acid (16 · 0 m 1), heated the entire solution to 50 ° C, and then added 3 -n-propyl-1 Η -pyridine in portions over a period of 30 minutes. The azole-5 carboxylic acid (Chem. Pham. Bull ·, 1 984, 11, 1 5 68; 16.4 g, 0.106 mol), while maintaining the reaction temperature below 60 ° C. The resulting solution was heated at 60 ° C for 18 hours, and then cooled and poured onto ice. The white precipitate was collected, washed with water, and then dried by suction to obtain the title compound (15.4 g). m · ρ_ · 17 0 — 172 ° C. -186- (Please read the precautions on the back before filling this page) This paper size is applicable to the Chinese National Standard (CNS) A4 specification (210X297). 524805 A7 B7 V. Description of the invention (184) Elemental analysis measurement: C, 4 2 · 3 5; Η, 4 · 5 6; N, 21 · 07. C7H9N304 calculates 値 c, 42.21; Η4.55; N, 21.1%. 5 (DMS〇d6): 0.90 (3H, t), 1.6 · 4 (2Η, m), 2 · 8 3 (2m, m), 14.00 (1H, s). Preparation 4 3 —Ethyl-1, 4-nitro-1, Η ~ d than d 坐 -5—contained acid was prepared from the title compound of Preparation 2 in a similar manner to Preparation 3 as a brown solid (64%). δ (DM S 0 d 6): 1.18 (3H, t), 2 · 8 4 (2 Η, m), 13.72 (lH, s). Preparation Example 5 Printed by the Consumer Cooperatives of the Central Bureau of Standards, Ministry of Economic Affairs ^ (Please read the precautions on the back before filling out this page) 4 Mononitro-3 -n-propyl-1 H-d than π sitting -5-formamidine A solution of the title compound (15.4 g, 0.07 7 m ο 1) in Thiochlorine (75 m 1) in Preparation Example 3 was heated under reflux for 3 hours, and then the cooled reaction mixture was reduced. After pressure evaporation, the residue was azeotroped with tetrahydrofuran (2 × 50 m 1), then the suspension was in tetrahydrofuran (50 m 1). The disturbed suspension was cooled with ice and treated with ammonia for 1 hour. Add water (50 m 1), and then evaporate the resulting mixture under reduced pressure. The paper size applies the Chinese National Standard (CNS) A4 (210X297 mm) -1 87-5248〇5 Printing A7 B7 V. Description of the invention (185) A solid was obtained. The solid was milled with water and dried by suction to obtain the title compound (1 4 · 3 g). 199 t :. Elemental analysis: 値 · C, 4 2 · 3 5; Η, 5 · 0 7; N, 2 8 · 38. C7H1ON4O3 calculates 値 C, 4 2 · 42; Η '5.0 · 9; N, 28.27%. (DMS〇d6): 0.90 (3H, t), 1.68 (2H, m), 2. 8 6 (2 Η, t), 7.6 (1 Η, s), 8. 0 (1 Alas, s). Preparation 6 3 -Ethyl-1 -nitro-1 -pyrazole-5 -methoxamine. From the title compound of Preparation 4 in a similar manner as in Preparation Example 5 was obtained 'as a white solid (90%). d (DMS〇d6): 1.17 (3H, t), 2. 8 7 (2 Η, m), 7.4 (1 H, s), 7. 6 〇 (1 Η, s), 7. 9 〇 (1 Alas, s). L R M S: m / z 185 (M + 1) +. Preparation Example 7 This paper size is in accordance with Chinese National Standard (CNS) A4 specification (210X 297 mm) -188- (Read the precautions on the back before filling this page)

524805 A7 B7 經濟部中央標準局員工消費合作社印製 五、發明説明（186) 4 — 胺 基 — 3 — 正 丙 基 — 1 Η -吡 唑 — 5 — 甲 醯 胺 令 製 備 例 5 標 題 化 合 物 ( 1〇 •〇 g 〇 • 〇 5 〇 m 〇 1 ) ， 1 〇 % 鈀 ( 於木 炭 上） (1 • 5 g ) 與 乙 醇 ( 4 〇 〇 m 1 ) 的 攪 拌 混 合 物 於 3 4 5 k P a ( 5 0 P S i ) 及 5 〇 °c 下 氫 化 1 8 小 時 然後 加以 'Μ 過 濾 〇 將 濾 液 與 濾 片 的 乙 醇 洗 液 ( 2 〇 0 m 1 ) 合倂 後減 壓 蒸 發 而 得 到 橙 色 固 體 此 固 體 以 乙 酸 乙 酯 甲 醇進 行結 晶 而 得 到 呈 白 色 固 體 之 標 題 化合 物 ( 6 • 8 g ) 〇 m • P • 1 9 6 — 2 〇 1 °c 〇 元 素 分析 實 測 値 C 4 8 • 9 6 ;Η 5 6 • 9 8 > N y 3 2 • 〇 8 〇 C 7 Η 1 .2 N 4〇； ;〇, • 2 Ε 3 Η 2 〇 丨計 ‘算 値 :C 5 4 8 • 6 8 > Η 7 • 3 〇 > Ν， 3 2 • 4 4 % 〇 5 ( D Μ S 〇 d 6 丨） • 〇 • 8 8 (3 Η， t ) 1 • 5 5 ( 2 Η 5 m ) 2 • 4 6 ( 2 Η ， t ) > 4 • 4 〇 ( 2 Η ， s ) 5 7 • 〇 〇 ( 1 Η ， s ) ， 7 • 1 2 ( 1 Η s ) ， 1 2 • 2 〇 ( 1 Η 5 S ) 0 製 備 例 8 4 一 胺 基 — 3 一 乙 基 — 1 Η - 吡唑 — 5 — 甲 醯 胺 由 製 備 例 6 之 標 題 化 合 物 依製 備例 7 之 類 似 方 式 製 得 呈棕色固體（80%)。 (請先閱讀背面之注意事項再填寫本頁) 本紙張尺度適用中國國家標準（CNS ) A4規格（210X297公釐）_ 1 89 - 524805 A7 B7 五、發明説明（18乃 5(DMS〇d6)：l-08(3H，t)， 2 · 4 5 ( 2 Η，Q ) ’ 4 · 5 〇（1 Η，s ) ’ 6 · 8 8 ( 1 Η，s ) ’ 7 · 1 0 ( 1 Η，s ) ’ 7 · 2 6 ( 2 Η，s )。 L R M S ： m / ζ 155(Μ+1)+。 製備例9 4 一（2 -正丙氧苄醯胺基）一 3 一正丙基—1Η 一 口比哇一 5 —甲醯胺 將2 —正丙氧苄醯氯（57 · 6它’ 0 · 291 m ο 1 )於二氯甲烷（5 0 m 1 )中所形成的溶液逐滴加 入一攪拌中而以冰冷卻之含有製備例7標題化合物（ 經濟部中央標準局員工消費合作社印製 (請先閱讀背面之注意事項再填寫本頁) 35 · Og ，〇 · 2〇8mo 1)與乾燥吡啶（35〇 m 1 )的懸浮液裡，在室溫下將此混合物攪拌1 8小時， 然後減壓蒸發。令殘餘物與甲苯（2 X 1 0 〇m 1 )共沸 ，再用乙醚（1 0 0 m 1 )對所得棕色固體加以碾製而得 到呈灰褐色固體之標題化合物（8 3 · 0 g )。 5(CH3〇Hd4):0.92(3H，t)， 1 · 1 4 ( 3 Η，t )， 1 · 6 5 ( 2 Η，m )， 1.94(2H，m)， 2 · 8 0 ( 2 Η，t )，524805 A7 B7 Printed by the Consumer Cooperatives of the Central Standards Bureau of the Ministry of Economic Affairs 5. Description of the invention (186) 4 —Amine — 3 —n-propyl — 1 Η -pyrazole — 5 — Formamidine Order Preparation Example 5 The title compound (1 • • 〇g billion square 〇5 〇m 〇1), square 1% palladium (on charcoal) (1 • 5 g) and ethanol (4 〇〇m 1) the mixture was stirred 3 4 5 k P a (5 0 PS i) and hydrogenated at 50 ° C. for 18 hours and then filtered by Μ. The filtrate was combined with an ethanol washing solution of the filter (2000 m 1) and evaporated under reduced pressure to obtain an orange solid. The solid was acetic acid. Ethyl methanol was crystallized to give the title compound (6 • 8 g) as a white solid. 〇m • P • 196 — 2 〇1 ° c 〇 Elemental analysis: 値 C 4 8 • 9 6; Η 5 6 • 9 8 > N y 3 2 • 〇8 〇C 7 Η 1.2 N 4〇;; 〇, • 2 Ε 3 Η 2 〇 Calculate the calculation: C 5 4 8 • 6 8 > Η 7 • 3 〇 > Ν, 3 2 • 4 4% 〇5 (D Μ S 〇d 6 丨) • 〇 • 8 8 (3 Η, t) 1 • 5 5 (2 Η 5 m) 2 • 4 6 (2 Η, t) > 4 • 4 〇 (2 Η, s) 5 7 • 〇〇 (1 Η, s), 7 • 1 2 (1 Η s), 1 2 • 2 〇 (1 Η 5 S) 0 Preparation Example 8 4 monoamino — 3 monoethyl — 1 Η-pyrazole — 5 — Formamidine was prepared as a brown solid (80%) from the title compound of Preparation 6 in a similar manner to Preparation 7. (Please read the precautions on the back before filling this page) This paper size is applicable to the Chinese National Standard (CNS) A4 specification (210X297 mm) _ 1 89-524805 A7 B7 V. Description of the invention (18 is 5 (DMS〇d6) : L-08 (3H, t), 2 · 4 5 (2 Η, Q) '4 · 5 〇 (1 Η, s)' 6 · 8 8 (1 Η, s) '7 · 1 0 (1 Η , S) '7 · 2 6 (2 Η, s). LRMS: m / ζ 155 (M + 1) +. Preparation Example 9 4 Mono (2-n-propoxybenzylamino)-3 n-propyl —1Η A mouthful of biwa-5 —methoxamine Dropwise a solution of 2-n-propoxybenzylhydrazone (57 · 6 ′ ′ 0 · 291 m ο 1) in dichloromethane (50 m 1) Add to agitation and cool with ice to contain the title compound of Preparation Example 7 (printed by the Consumer Cooperative of the Central Bureau of Standards of the Ministry of Economic Affairs (please read the precautions on the back before filling out this page) 35 · Og, 〇 2〇8mo 1) In a suspension with dry pyridine (350,000 m 1), the mixture was stirred at room temperature for 18 hours, and then evaporated under reduced pressure. The residue was azeotroped with toluene (2 X 100 m 1) and reused. Diethyl ether (100 m 1) gave the resulting brown solid It was milled to obtain the title compound (83. 0 g) as a beige solid. 5 (CH3OHd4): 0.92 (3H, t), 1 · 1 4 (3Η, t), 1 · 6 5 ( 2 Η, m), 1.94 (2H, m), 2 · 8 0 (2 Η, t),

本紙張尺度適用中國國家標準（CNS ) A4規格（210X297公釐）~~Jg〇T 524805 A7 B7 五、發明説明（188) 4 · 2 0 ( 2 Η，t )， 7 ·〇 8 ( 1 Η，m )， 7 · 1 8 ( 1 Η，d )， 7 · 5 2 ( 1 Η，m )， 8 · 0 4 ( 1 Η，d )。 LRMS:m/z 3 3 1 ( Μ + 1 ) +。 製備例1 0 3 —乙基—4 一（2 —正丙氧苄醯胺基）一1Η — 〇比 唑一 5 —甲醯胺 (請先閲讀背面之注意事項再填寫本頁) 得 製 式 方 似 類 之 9 例 備 製 依 物 合 化 題 標 之 8 例 備 製 由 經濟部中央標隼局員工消費合作社印製 體 dHHHHHHHHHHl o oo CXI 2 2 1 i—II i—I i—_ i—- /IV s rv /(V rv /' r\ /IV /(V rv rv rv nw 褐 M261560 -0 00 22 灰 D1871022459 · ， 51—^li—-24777777-_ % 8 6 Η 3 /(V 3 9 〇 \)/ \My \)/ N)y \)y \)y \)y tQmtmdssmdThis paper size applies Chinese National Standard (CNS) A4 specification (210X297 mm) ~~ Jg〇T 524805 A7 B7 V. Description of the invention (188) 4 · 2 0 (2 2, t), 7 · 〇 8 (1 Η , M), 7 · 1 8 (1 Η, d), 7 · 5 2 (1 Η, m), 8 · 0 4 (1 Η, d). LRMS: m / z 3 3 1 (M + 1) +. Preparation Example 1 0 3 —Ethyl — 4 (2 —n-propoxybenzylamine) — 1 — — 〇biazole — 5 — formamide (Please read the precautions on the back before filling out this page) Nine examples of similar ones were prepared according to the combination of physical and chemical problems. Eight cases were prepared by the Consumers' Cooperatives printed by the Central Bureau of Standards of the Ministry of Economic Affairs dHHHHHHHHHHHl o oo CXI 2 2 1 i—II i—I i — — — i — -/ IV s rv / (V rv / 'r \ / IV / (V rv rv rv nw Brown M261560 -0 00 22 Gray D1871022459 ·, 51— ^ li—-24777777-_% 8 6 Η 3 / (V 3 9 〇 \) / \ My \) / N) y \) y \) y \) y tQmtmdssmd

H 本紙張尺度適用中國國家標準（CNS ) A4規格（210X297公釐）-彳91 - 524805 A7 B7五、發明説明（189) LRMS:m/z 317(M+1)+。 製備例1 1 4— (2 —乙氧爷酸胺基）一 3 —正丙基一1 Η — 口比 唑一 5 —甲醯胺 由製備例7之標題化合物及2 -乙氧苄醯氯依製備例 9之類似方式製得，呈白色固體（64%)。 πι· ρ · 20 9 — 211。。。 元素分析實測値：C，60 · 73 ; Η，6 · 4 1 ; N， 17 · 8 0 。C16H2〇N4〇3計算値 C ，6 0 · 74 ； Η，6.37;Ν，17·71%。 經濟部中央標準局員工消費合作社印製 ••tmtQmmmd ， 、"""/5Ϊ-5955·/·/ 「一11一 I 一 deHHHHHH HHll 032221221(( S Γν /IV rv /fv /IV /(V Γν ο 6 Μ 2657722049 D45720250 . . X.—\····*·*· OW οο Γο τ—_ τ—_ τ—14 τ τ τ 8 ^ι~_ ο \)/ \)/ \lyH This paper size applies to the Chinese National Standard (CNS) A4 specification (210X297 mm)--91-524805 A7 B7 V. Description of the invention (189) LRMS: m / z 317 (M + 1) +. Preparation Example 1 1 4— (2-Ethoxyacetic acid amine group) —3—n-propyl-1 hydrazone—orbitazol-5—formamidine was prepared from the title compound of Preparation 7 and 2-ethoxybenzyl chloride Prepared in a similar manner to Preparation Example 9 as a white solid (64%). π · ρ · 20 9 — 211. . . Elemental analysis: 値: C, 60 · 73; Η, 6 · 4 1; N, 17 · 80. C16H2ON4O3 calculates 値 C, 60.74; Η, 6.37; N, 17.71%. Printed by the Consumer Cooperatives of the Central Bureau of Standards, Ministry of Economic Affairs • tmtQmmmd, " " " / 5Ϊ-5955 (V Γν ο 6 Μ 2657722049 D45720250 ... .. X .— \ ··· **** OW οο Γο τ—_ τ—_ τ—14 τ τ τ 8 ^ ι ~ _ ο \) / \) / \ ly

s S Η 3 /(\ 2 8 2 τ—Η 例 備 製 (請先閲讀背面之注意事項再填寫本頁)s S Η 3 / (\ 2 8 2 τ—Η Example Preparation (Please read the precautions on the back before filling this page)

本紙張尺度適用中國國家標準（CNS ) Α4規格（21〇Χ 297公釐）-192 - 524805 經濟部中央標準局員工消費合作社印^ kl B7 五、發明説明（19〇) 5 —（2 —正丙氧苯基）一3 -正丙基一 1 ，6 -二 氫〜7H —吡唑並〔4，3 - d〕嘧啶一 7 —酮 在氮氣下將第三丁氧化鉀（93 · Og，0 · 832 m 0 1 )分批加入一攪拌中而含有製備例9標題化合物（ 83 ·〇g ，〇· 25m〇 1)及 2 —丙醇（8〇0ml )之溶液裡，令混合物加熱迴流1 8小時，然後冷卻。加 水（1 0 0 m 1 )而得均質溶液，此溶液以2 Μ之氫氯酸 酸化至ρ Η 6，析出的白色沈澱物經收集並抽氣乾燥而得 標題化合物（3 7 · 4 g )。 元素分析實測値：C，6 5 · 3 6 ; Η，6 · 4 9 ; N， 17 · 99 。Ci7H2〇N4〇2計算値 C，65 · 37 ; Η’6·45;Ν，17·94%。 <5(CDCl3)：l.〇5(3H^t)^ 1 · 1 6 ( 3 Η，t )， 2，〇〇(4H，m)， 3 · 〇 4 ( 2 H，t )， 4 · 2 〇（2 H，t )， 7 · 〇 7 ( 1 H，d )， 7 · 1 6 ( 1 H，m )， 7 · 4 8 ( 1 H，m )， 8 · 5 2 ( 1 H，d )， 11.30(1H，s)， 1 2 . 2 5 ( 1 H > s ) ° LRMS:m/z 313(M+1)+。 本紙張尺度適用中國國家標率（CNS ) A4規格（21 OX ：297公釐）-193 - (讀先閱讀背面之注意事項再填寫本頁)This paper size applies Chinese National Standard (CNS) A4 specification (21〇 × 297mm) -192-524805 Printed by the Consumers' Cooperative of the Central Standards Bureau of the Ministry of Economic Affairs ^ kl B7 V. Description of the invention (19〇) 5 — (2 — positive Propoxyphenyl) -3-n-propyl-1,6-dihydro ~ 7H-pyrazolo [4,3-d] pyrimidin-7-one under nitrogen nitrogen potassium third butoxide (93 0 · 832 m 0 1) was added in portions to a solution containing the title compound of Preparation Example 9 (83 · g, 0.25 m1) and 2-propanol (800 ml), and the mixture was heated to reflux. 18 hours, then cooled. Water (100 m 1) was added to obtain a homogeneous solution. This solution was acidified with 2 M hydrochloric acid to ρ Η 6. The precipitated white precipitate was collected and dried by suction to obtain the title compound (3 7 · 4 g) . Elemental analysis: 値: C, 6 5 · 3 6; Η, 6 · 4 9; N, 17 · 99. Ci7H2ON4O2 calculates 値 C, 65 · 37; Η '6.45; N, 17.94%. < 5 (CDCl3): 1.05 (3H ^ t) ^ 1 · 16 (3H, t), 2,00 (4H, m), 3 · 〇4 (2H, t), 4 · 2〇 (2 H, t), 7 · 〇7 (1 H, d), 7 · 16 (1 H, m), 7 · 4 8 (1 H, m), 8 · 5 2 (1 H , D), 11.30 (1H, s), 1 2. 2 5 (1 H > s) ° LRMS: m / z 313 (M + 1) +. This paper size applies to China National Standards (CNS) A4 specifications (21 OX: 297 mm) -193-(Read the precautions on the back before filling this page)

、1T 524805 A7 B7 五、發明説明（191) 製備例1 3 3 —乙基—5 —（2 -正丙氧苯基）一1 ，6 —二氫 一 7 Η —吡唑並〔4，3 — d〕嘧啶一 7 —酮 由製備例1 0之標題化合物依製備例1 2之類似方式 製得，呈白色固體（85%)。 5(DMS〇d6):〇.95(3H，t)， 1 · 1 5 ( 3 Η，t )， 1 · 7 2 ( 2 Η，m )， 2 · 8 4 ( 2 Η，Q )， 4 ·〇 3 ( 2 Η，t )， 7 · Ο 6 ( 1 Η，m )， 7 · 1 5 ( 1 Η，d )， 7 · 4 4 ( 1 Η，m )， 7 · 7 2 ( 1 Η，d )， 11.83(lH，s)， 1 3 · 6 4 ( 1 Η，s )。 經濟部中央標準局員工消費合作社印製 (請先閱讀背面之注意事項再填寫本頁) LRMS :m/z 299 (M+l) +。 製備例1 4 5 —（2 —乙氧苯基）一3 —正丙基—1，6 —二氫 一 7 Η — d比π坐並〔4，3 — d〕喃d定—7 —酮 由製備例1 1之標題化合物依製備例1 2之類似方式 製得，呈白色固體（88%)。 本紙張尺度適用中國國家標準（CNS ) A4規格（210X 297公釐）-1 94 - 524805 A7 _______B7__ 五、發明説明（192) in· p · 199 — 2 0 1C。 元素分析實測値：C，6 4 · 4 4 ; Η，6 · 1 9 ; N， 18 · 44。C16H18N4〇2計算値 C ，6 4 · 41 ； Η，6·〇8;Ν，18·78%。 5(CDCl3):l.〇8(3H，t)， 1 · 6 5 ( 3 Η，t )， 1 · 9 8 ( 2 Η，m )， 3 ·〇 4 ( 2 Η，t )， 4 · 3 6 ( 2 Η，q )， 7 · 1 〇（1 Η，d )， 7 · 2 〇（1 Η，m )， 7 · 5 0 ( 1 Η ，m )， 5 7 ( 1 Η ，d ) 5 • 3 6 ( 1 Η， s )， • 8 8 ( 1 Η ， s )。 製備例1 5 經濟部中央標準局員工消費合作社印製 (請先閱讀背面之注意事項再填寫本頁) 5 — (2 -院氧苯基）一 3 —院基一 1，6 —二氣一 7 Η -吡唑並〔4，3 - d〕嘧啶一 7 -酮類之烷基化 利用五種槪括步驟即方法A至E將製備例1 2，1 3 ，1 4之標題化合物N -烷基化。在數種情形下N 1 -及 N 2 -異構物可由相同反應分離出來。, 1T 524805 A7 B7 V. Description of the invention (191) Preparation example 1 3 3 -Ethyl-5-(2-n-propoxyphenyl) -1,6-dihydro-7 fluorene-pyrazolo [4,3 — D] pyrimidine-7-one was prepared from the title compound of Preparation Example 10 in a similar manner to Preparation Example 12 as a white solid (85%). 5 (DMS〇d6): 0.95 (3H, t), 1 · 1 5 (3 Η, t), 1 · 7 2 (2 Η, m), 2 · 8 4 (2 Η, Q), 4 · 〇3 (2 Η, t), 7 · Ο 6 (1 Η, m), 7 · 1 5 (1 Η, d), 7 · 4 4 (1 Η, m), 7 · 7 2 (1 Η , D), 11.83 (lH, s), 1 3 · 6 4 (1 Η, s). Printed by the Consumers' Cooperative of the Central Standards Bureau of the Ministry of Economic Affairs (please read the notes on the back before filling this page) LRMS: m / z 299 (M + l) +. Production Example 1 4 5 — (2-Ethoxyphenyl) —3—n-propyl—1,6—dihydro—7 Η — d ratio and π and [4,3 — d] pyridin-7—one From the title compound of Preparation 11 in a similar manner to Preparation 12 as a white solid (88%). This paper size applies to China National Standard (CNS) A4 specification (210X 297 mm) -1 94-524805 A7 _______B7__ V. Description of the invention (192) in · p · 199 — 2 0 1C. Elemental analysis: 値: C, 6 4 · 4 4; Η, 6 · 1 9; N, 18 · 44. C16H18N4〇2 calculates 値 C, 6 4 · 41; Η, 6.08; N, 18.78%. 5 (CDCl3): 1.08 (3H, t), 1.66 (3 Η, t), 1.98 (2 Η, m), 34.04 (2 Η, t), 4 3 6 (2 Η, q), 7 · 1 〇 (1 Η, d), 7 · 2 〇 (1 Η, m), 7 · 5 0 (1 ，, m), 5 7 (1 ，, d) 5 • 3 6 (1 Η, s), • 8 8 (1 Η, s). Preparation Example 1 5 Printed by the Consumer Cooperatives of the Central Bureau of Standards of the Ministry of Economic Affairs (please read the precautions on the back before filling out this page) 5 — (2-courtyard oxyphenyl) one 3 — courtyard one 1, 6 — two gas one 7 Alkylation of pyrene-pyrazolo [4,3-d] pyrimidin-7-ones The title compound N of Preparation Examples 1, 2, 3, and 14 was prepared using five inclusive steps, namely methods A to E- Alkylation. In several cases, the N 1-and N 2-isomers can be separated by the same reaction.

方法A 本紙張尺度適用中國國家標準（CNS ) A4規格（21 ox 297公釐）_ 195 _ 經濟部中央標牟局員工消費合作社印製 524805 A7 _ B7 五、發明説明（193) 在氮氣下將鹵化烷（2 · 7 5mmo 1 )加入一攪拌 中而由該吡唑並〔4，3 — d〕嘧啶酮受質（2 · 5 mmo 1)及1M氫氧化鈉水溶液（7 · 25mmo 1) 所形成的懸浮液裡。在5 0 °C下加熱該反應混合物7 2小 時，然後令其冷卻，以乙酸乙酯（2 X 2 5 m 1 )對整個 混合物進行萃取，萃取液合倂並經乾燥（M g S 0 4 )後減 壓蒸發而得粗產物，再以管柱層析法於矽膠上純化。Method A The paper size is in accordance with the Chinese National Standard (CNS) A4 specification (21 ox 297 mm) _ 195 _ Printed by the Central Consumer Bureau of the Ministry of Economic Affairs Consumer Cooperative 524805 A7 _ B7 V. Description of the invention (193) Under nitrogen Halogenated alkane (2.75mmo 1) was added to a stirrer and the pyrazolo [4,3-d] pyrimidone substrate (2.5mmo 1) and 1M aqueous sodium hydroxide solution (7.525mmo 1) were added. Formed into a suspension. The reaction mixture was heated at 50 ° C for 7 hours, and then allowed to cool. The whole mixture was extracted with ethyl acetate (2 X 2 5 m 1), and the extract was combined and dried (M g S 0 4 ) And evaporated under reduced pressure to obtain the crude product, which was then purified on silica gel by column chromatography.

方法B 在氮氣下將6 0 % w/w氫化鈉礦油分散液（ 〇· 3 9 m m ο 1 )加入一攪拌中且以冰冷卻之該受質（ 〇 · 39mmo 1 )於無水四氫呋喃（8ml )中所形成 的溶液裡。於0 °C 1小時後添加該鹵化烷（〇 · 4 3 mmol)，再於4 5 °C將反應混合物加熱2 4小時，然 後冷卻。混合物經減壓蒸發後令殘餘物於乙酸乙酯（4 0 m 1 )及鹽水（3 0 m 1 )之間分配。分離出有機相後乾 燥（M g S 0 4 )並減壓蒸發而得粗產物，再以管柱層析法 於矽膠上純化。Method B: Add 60% w / w sodium hydride mineral oil dispersion (0.39 mm 1) to a stirred and ice-cooled substrate (0.39mmo 1) in anhydrous tetrahydrofuran (8ml) under nitrogen. ). After 1 hour at 0 ° C, the alkyl halide (0.43 mmol) was added, and the reaction mixture was heated at 4 5 ° C for 24 hours, and then cooled. After the mixture was evaporated under reduced pressure, the residue was partitioned between ethyl acetate (40 m 1) and brine (30 m 1). The organic phase was separated, dried (M g S 0 4) and evaporated under reduced pressure to obtain the crude product, which was then purified on silica gel by column chromatography.

方法C 在氮氣下將雙（三甲矽烷基）胺化鈉於四氫呋喃中所 形成的2 Μ溶液（2 · 2 m m ο 1 )逐滴加入一攪拌中且 以冰冷卻而由該受質（2 m m ο 1 )於無水四氫呋喃（8 m 1 )中所形成的溶液裡。在〇 °c下攪拌1小時，再令其 本紙張尺度適用中國國家標準（CNS ) A4規格（210X297公釐）-1 96 - (讀先閱讀背面之注意事項再填寫本頁) 、11 524805 A7 B7_ 五、發明説明（194) 冷卻至一 7 0 °C。接著添加該鹵化烷（2 m m ο 1 )，移 開冷卻浴，再於室溫下將溶液攪拌2 4小時。減壓蒸發後 令殘餘物於乙酸乙酯（4 0 m 1 )與碳酸氫鈉水溶液（ 3 0 m 1 )之間分配，然後把有機相分離出來，經乾燥（ M g S ◦ 4 )後減壓蒸發得粗產物，再以管柱層析法於矽膠 上純化。 或者可使用0 · 5 Μ雙（三甲矽烷基）胺化鉀的甲苯 溶液’以無水甲苯爲溶劑，在大約4 0 °C之溫度進行烷化 反應2 0小時。Method C: A 2 M solution (2.2 mm ο 1) of sodium bis (trimethylsilyl) amine in tetrahydrofuran was added dropwise to a stirring solution under nitrogen, and the mass was cooled by ice (2 mm ο 1) in a solution formed in anhydrous tetrahydrofuran (8 m 1). Stir at 0 ° C for 1 hour, then make the paper size applicable to the Chinese National Standard (CNS) A4 specification (210X297 mm) -1 96-(Read the precautions on the back before filling in this page), 11 524805 A7 B7_ V. Description of the invention (194) Cool to -7 ° C. Then, the halogenated alkane (2 mm 1) was added, the cooling bath was removed, and the solution was stirred at room temperature for 24 hours. After evaporation under reduced pressure, the residue was partitioned between ethyl acetate (40 m 1) and aqueous sodium bicarbonate solution (30 m 1), and then the organic phase was separated, dried (M g S ◦ 4), and then reduced. The crude product was obtained by pressure evaporation and purified by column chromatography on silica gel. Alternatively, a 0.5 M solution of potassium bis (trimethylsilyl) amine in toluene can be used for the alkylation reaction at about 40 ° C for 20 hours using anhydrous toluene as a solvent.

方法D 經濟部中央標準局員工消費合作社印製 (請先閱讀背面之注意事項再填寫本頁) 在氮氣下將含有該受質（4 · 8mmo 1 )，鹵化院 (4 · 8 m m 〇 1 ) ， Aliquat (TM) 336 (15〇 m g )及二氯甲烷（8 0 m 1 )的溶液加入一攪拌中的 1 Μ氫氧化鈉水溶液（1 5 m m ο 1 )裡.在室溫下將此 兩相混合物劇烈攪拌7 2小時，把水相分離出來後用乙酸 乙酯（2 X 2 5 m 1 )萃取之，再把萃取液和有機相合倂 並乾燥（M g S 0 4 )，經減壓蒸發得粗產物，再以管柱層 析法於矽膠上加以純化。Method D Printed by the Consumer Cooperatives of the Central Bureau of Standards of the Ministry of Economic Affairs (please read the precautions on the back before filling this page). This substrate will be contained under nitrogen (4 · 8mmo 1) and halogenated institute (4 · 8 mm 〇1) A solution of Aliquat (TM) 336 (150 mg) and dichloromethane (80 m 1) was added to a stirred 1 M aqueous sodium hydroxide solution (15 mm ο 1). The two were stirred at room temperature. The phase mixture was stirred vigorously for 7 2 hours. The aqueous phase was separated and extracted with ethyl acetate (2 X 2 5 m 1). The extract was combined with the organic phase and dried (M g S 0 4). The crude product was evaporated and purified by column chromatography on silica gel.

方法E 將三苯基膦（1 . 77mmo 1)及該烷醇（ 1 · 77mmo 1)加入一攪拌中而由該受質（1 · 60 m m ο 1 )於無水四氫呋喃（1 〇 m 1 )中所形成的溶液 本紙張尺度適用中國國家標準（CNS ) A4規格（210X297公釐） 524805 A7 B7 五、發明説明（195) 裡。把產生的溶液冷卻至一 5 t；，再逐滴添加偶氮二羧酸 二乙酯（1 · 7 7 m m ο 1 )。接著令反應混合物回復至 室溫’攪拌1 8小時後減壓蒸發。將殘餘物於乙酸乙酯（ 3 0 m 1 )和水（3 〇 m 1 )之間分配，把有機相分離出 來後與水相的乙酸乙酯萃取液（5 〇 m 1 )合倂，經乾燥 (N a 2 S 0 4 )後蒸發而得粗產物，再以管柱層析法於矽 膠上純化。 製備例1 6 3 —乙基一 5 —（2 —正丙氧苯基）一1—(吡啶一 2 —基）甲基一 1，6—二氫一 7H —吡唑並〔4，3 — d〕嘧啶一 7 -酮 由製備例1 3之標題化合物及2 -氯甲基吡啶依製備 例1 5 B之步驟製得，呈白色泡沬狀（1 5 % )。 5(CDCl3):l.i8(3H，t)， 1 · 4 3 ( 3 Η，t )， (讀先閱讀背面之注意事項再填寫本頁)Method E Triphenylphosphine (1.777mmo 1) and the alkanol (1.777mmo 1) are added to a stirrer and the substrate (1.660mm ο 1) is added to anhydrous tetrahydrofuran (100m1). The size of the solution formed on this paper is in accordance with Chinese National Standard (CNS) A4 (210X297 mm) 524805 A7 B7 5. In the description of the invention (195). The resulting solution was cooled to 5 t; then diethyl azodicarboxylate (1.77 mm m ο 1) was added dropwise. The reaction mixture was then returned to room temperature 'and stirred for 18 hours, and then evaporated under reduced pressure. The residue was partitioned between ethyl acetate (30 m 1) and water (300 m 1). The organic phase was separated and combined with the aqueous ethyl acetate extract (50 m 1). The crude product was obtained after drying (N a 2 S 0 4) and evaporation, and then purified by column chromatography on silica gel. Production Example 1 6 3 -Ethyl-5-(2-n-propoxyphenyl) -1- (pyridine-2-yl) methyl-1,6-dihydro-7H-pyrazolo [4,3 — d] Pyrimidine-7-one was prepared from the title compound of Preparation Example 13 and 2-chloromethylpyridine according to the procedure of Preparation Example 15B, and was white foamy (15%). 5 (CDCl3): l.i8 (3H, t), 1 · 4 3 (3 Η, t), (Read the precautions on the back before filling this page)

、1T 經濟部中央標隼局員工消費合作社印製 02853660 nw nw i~ CD 1± CO 23457777, 1T Printed by the Consumer Cooperatives of the Central Bureau of Standards, Ministry of Economic Affairs 02853660 nw nw i ~ CD 1 ± CO 23457777

/l\ /i\ /IV κί\ r\/ l \ / i \ / IV κί \ r \

Ji Ji THX THX THX Tr_ Tr_ TL1 Tr_ Tr_ Tui ΤΓ Tr_ 22222211 \)y \)y \)y \ly 本紙張尺度適用中國國家標準（CNS ) Α4規格（210Χ297公釐） 經濟部中央標準局員工消費合作社印製 524805 A7 B7 五、發明説明（196) 8 · 5 2 ( 1 Η，d )， 8 · 5 8 ( 1 Η，d )， 11.20(lH，s)。 LRMS:m/z 39〇（M+1)+。 製備例1 7 5 -（2 -正丙氧苯基）一 3 —正丙基一 1 一（吡啶 一 2 —基）甲基一1 ，6 —二氫—7H —吡唑並〔4，3 一 d〕嘧啶一 7 -酮 由製備例1 2之標題化合物及2 -氯甲基吡啶依製備 例1 5 D之步驟製得，呈白色泡沫狀（2 2 % )。 5 ( C D C 1 a ) :1·〇1(3Η，ΐ)， 1 · 1 7 ( 3 Η，t )， 1 · 9 0 ( 2 Η，m )， 2 ·〇 0 ( 2 Η，m )， 2 · 9 9 ( 2 Η，t )， 4 · 2 〇（2 Η，t )， Φ 5 · 9 6 ( 2 Η，s )， 6 · 9 9 ( 1 Η，d )， 7 ·〇 5 ( 1 Η，d )， 7 · 1 7 ( 2 Η，m )， 7 · 4 4 ( 1 Η，m )， 7 · 6 〇（1 Η，m )， 8 · 5 4 ( 1 Η，d )， 本紙張尺度適用中國國家標準（CNS ) Α4規格（210X 297公釐)~^99 (請先閱讀背面之注意事項再填寫本頁 丁 524805 A7 B7 五、發明説明（197) 8 . 5 9 ( 1 Η，d )， 11.2〇（lH，s)° (讀先閱讀背面之注意事項再填寫本頁) LRMS :m/z 404 (M+l)+。 製備例1 8 3 —乙基—5 —（2 —正丙氧苯基）一2 —（吡啶一 2 —基）甲基一2，6 —二氫一7H —吡唑並〔4，3 — d〕嘧啶一 7 -酮 由製備例1 3之標題化合物及2 -氯甲基吡啶依製備 例15B之步驟製得，呈白色固體（22%)。 5(CDC'l3):1.12(3H，t)， 1 · 3 〇（3 Η，t )， 1 · 9 9 ( 2 Η，m )， 3 ·〇〇（2 Η ， Q )， 4 · 1 7 ( 2 Η，t )， 5 · 6 8 ( 2 Η ， s )， 經濟部中央標準局員工消費合作社印製Ji Ji THX THX THX Tr_ Tr_ TL1 Tr_ Tr_ Tui ΤΓ Tr_ 22222211 \) y \) y \) y \ ly This paper size applies to the Chinese National Standard (CNS) Α4 specification (210 × 297 mm) Employees' Cooperatives of the Central Standards Bureau of the Ministry of Economic Affairs Printed 524805 A7 B7 V. Description of the invention (196) 8 · 5 2 (1 Η, d), 8 · 5 8 (1 Η, d), 11.20 (lH, s). LRMS: m / z 39 ° (M + 1) +. Preparation Example 1 7 5-(2-n-propoxyphenyl) -3-n-propyl-1 1- (pyridine-2-yl) methyl-1,6-dihydro-7H-pyrazolo [4,3 1d] Pyrimidine-7-one was prepared from the title compound of Preparation Example 12 and 2-chloromethylpyridine according to the procedure of Preparation Example 15D, and showed a white foam (22%). 5 (CDC 1 a): 1.0 · 1 (3Η, ΐ), 1 · 17 (3Η, t), 1 · 9 0 (2Η, m), 2 · 〇0 (2Η, m), 2 · 9 9 (2 Η, t), 4 · 2 〇 (2 Η, t), Φ 5 · 9 6 (2 Η, s), 6 · 9 9 (1 Η, d), 7 · 〇 5 ( 1 Η, d), 7 · 1 7 (2 Η, m), 7 · 4 4 (1 Η, m), 7 · 6 〇 (1 Η, m), 8 · 5 4 (1 Η, d), This paper size applies to Chinese National Standard (CNS) A4 specification (210X 297 mm) ~ ^ 99 (Please read the notes on the back before filling in this page D. 524805 A7 B7 V. Description of the invention (197) 8. 5 9 (1 Η, d), 11.2〇 (lH, s) ° (read the precautions on the back before filling this page) LRMS: m / z 404 (M + l) +. Preparation Example 1 8 3 —ethyl — 5 — (2-N-propoxyphenyl) -2- (pyridine-2-yl) methyl-2,6-dihydro-7H-pyrazolo [4,3-d] pyrimidin-7-one was prepared from Preparation Example 1 The title compound of 3 and 2-chloromethylpyridine were prepared according to the procedure of Preparation Example 15B as a white solid (22%). 5 (CDC'l3): 1.12 (3H, t), 1.30 (3, t), 1 · 9 9 (2 Η, m), 3 Thousand and (2 Η, Q), 4 · 1 7 (2 Η, t), 5 · 6 8 (2 Η, s), Ministry of Economic Affairs Bureau of Standards staff printed consumer cooperatives

4mmmd d ， lx J J ， ， ， 一了「一 z • HHH Η Η 1 \ 7— IX 1—I r—Η /IVm I Γ\ /IV Γν /(V /(V VI ·. 0020 〇 88s o 2 4 6 4 5 M ······ c u 7777881L Η 3 c' m 〇 〇 s 3 + Μ 本紙張尺度適用中國國家標準（CNS ) A4規格（210X 297公釐）-2〇〇 _ 經濟部中央標準局員工消費合作社印製 524805 A7 B7 五、發明説明（198) 製備例1 9 5 — (2 —乙氧苯基）—3 —正丙基—2 —（吡啶一 2 —基）甲基—2，6 -二氫一 7H —吡唑並〔4，3 — d〕嘧啶一 7 -酮 由製備例1 4之標題化合物及2 -氯甲基吡啶依製備 例1 5 B之步驟製得，呈白色泡沬狀（5 9 % )。 5 ( C D C 1 3 ):〇.98(3H，t)， 1 · 6 0 ( 3 Η，t )， 1 · 7 6 ( 2 Η，m )， 2 · 9 8 ( 2 Η，t )， 4 · 3 Ο ( 2 Η，Q )， 5 · 7 Ο ( 2 Η，s )， 7 ·〇 6 ( 2 Η，m )， 7.15(lH，m)， 7 · 2 2 ( 1 Η，m )， 7.44(lH，m)， 7 · 6 2 ( 1 Η，m )， 8 · 4 1 ( 1 Η，d )， 8 · 5 9 ( 1 Η，d )， 10.9〇（lH，s)。 L R M S ： m / z 39〇（M+1) +。 製備例2〇 本紙張尺度適用中國國家標準（CNS ) Α4規格（210X297公釐）_ 201 _ (讀先閲讀背面之注意事項再填寫本頁) 4. 經濟部中央標準局員工消費合作社印製 524805 kl B7 五、發明説明（199) 5 — (2 —正丙氧苯基）一 3 -正丙基—2 -（吡口定 一 2 —基）甲基一 2，6 —二氫一 7H —吡唑並〔4，3 —d〕喃II定一 7 -丽 由製備例1 2之標題化合物及2 -氯甲基吡啶依製備 例1 5 B之步驟製得，呈白色泡沫狀（5 4 % )。 5 ( C D C 1 3 ):〇.98(3H，t)， 1 · 1 6 ( 3 Η，t )， 1 · 7 7 ( 2 Η，m )， 2 · 0 〇（2 Η，m )， 2 . 9 9 ( 2 Η，t )， 4 · 1 9 ( 2 Η，t )， 5 · 7 4 ( 2 Η，s )， 7·〇4 — 7·16(1Η，ιη)， 7 · 2 0 ( 1 Η，m )， 7 · 4 4 ( 1 Η，m )， 7 · 6 4 ( 1 Η，m )， 8 · 4 1 ( 1 Η，d )， 8 · 5 9 ( 1 Η，d )， l〇.90(lH，s)° LRMS :m/z 404 (M+l)+。 製備例2 1 5 -（2 —正丙氧苯基）一 3 —正丙基一 2 -（d比口定 一 2 —基）甲基一 2，. 6 —二氫一7H — D比d坐並〔4，3 本紙張尺度適用中國國家標準（CNS ) A4規格（210X 297公釐）-202 - (讀先閱讀背面之注意事項再填寫本頁4mmmd d, lx JJ,,, "a z • HHH Η Η 1 \ 7— IX 1—I r—Η / IVm I Γ \ / IV Γν / (V / (V VI ·. 0020 〇88s o 2 4 6 4 5 M ······ cu 7777881L Η 3 c 'm 〇〇s 3 + Μ This paper size applies Chinese National Standard (CNS) A4 specification (210X 297 mm)-2〇_ Central Ministry of Economic Affairs Printed by the Consumer Bureau of the Standards Bureau 524805 A7 B7 V. Description of the invention (198) Preparation Example 1 9 5 — (2 —Ethoxyphenyl) — 3 —n-propyl — 2 — (pyridine 2 —yl) methyl — 2,6-dihydro-7H-pyrazolo [4,3-d] pyrimidin-7-one was prepared from the title compound of Preparation 14 and 2-chloromethylpyridine according to the procedure of Preparation 15B. It was white foam-like (59%). 5 (CDC 1 3): 0.98 (3H, t), 1. 6 0 (3 Η, t), 1 · 7 6 (2 Η, m), 2 · 9 8 (2 Η, t), 4 · 3 Ο (2 Η, Q), 5 · 7 Ο (2 Η, s), 7 · 〇 6 (2 Η, m), 7.15 (lH, m), 7 · 2 2 (1 Η, m), 7.44 (lH, m), 7 · 6 2 (1 Η, m), 8 · 4 1 (1 Η, d), 8 · 5 9 (1 Η, d) , 10.9〇 (lH, s) LRMS: m / z 39〇 (M + 1) +. Preparation Example 2 The paper size is applicable to the Chinese National Standard (CNS) A4 specification (210X297 mm) _ 201 _ (Read the precautions on the back before filling in this Page) 4. Printed by the Consumer Cooperatives of the Central Bureau of Standards of the Ministry of Economic Affairs 524805 kl B7 V. Description of the invention (199) 5 — (2 —n-propoxyphenyl) — 3 —n-propyl — 2 — (Pyridoxine 2) —Yl) methyl-2,6-dihydro-7H —pyrazolo [4,3-d] pyridinyl-7-triazine from the title compound of Preparation 12 and 2-chloromethylpyridine It was obtained in the step of 15 B, and it was white foam (54%). 5 (CDC 1 3): 0.98 (3H, t), 1 · 1 6 (3 Η, t), 1 · 7 7 ( 2 Η, m), 2 · 0 〇 (2 Η, m), 2. 9 9 (2 Η, t), 4 · 19 (2 Η, t), 5 · 7 4 (2 Η, s), 7.04 — 7 · 16 (1Η, ιη), 7 · 2 0 (1 Η, m), 7 · 4 4 (1 Η, m), 7 · 6 4 (1 Η, m), 8 · 4 1 (1 Η, d), 8.59 (1 Η, d), 10.90 (lH, s) ° LRMS: m / z 404 (M + 1) +. Preparation Example 2 1 5-(2-n-propoxyphenyl) -3-n-propyl- 2-(d than lipidine a 2 -yl) methyl-2 ,. 6 -dihydro-7H-D ratio d Sit down [4, 3 This paper size applies to Chinese National Standard (CNS) A4 specifications (210X 297 mm) -202-(Read the precautions on the back before filling in this page

、1T 524805 經濟部中央標準局員工消費合作社印製 A7 B7 五、發明説明（200) —d〕嘧u定—7 -酮 由製備例1 2之標題化合物及3 -氯甲基吡啶依製備 例1 5 B之步驟製得，呈乳泡沫狀（3 2 % )。 5 ( C D C 1 a ) :〇.98(3H，t)， 1 · 1 4 ( 3 Η，t )， 1 · 78 (2H5m)， 2 ·〇〇（2 Η ， m )， 2 · 9 2 ( 2 Η，t )， 4 . 1 9 ( 2 Η，t )， 5 · 5 8 ( 2 Η，s )， 7 ·〇 4 ( 1 Η，d )， 7 · 1 4 ( 1 Η，m )， 7 . 24 (lH^m)， 7.43 (lH，m)， 7.48 (1H，m)， 8 · 4 0 ( 1 H，d )， 8.59 (2H，m)， 1〇.91(1H，s)。 LRMS:m/z 4〇4(M+1)+。 製備例2 2 4 — (2 —苯乙烯基）嗒哄 將氯化鋅（8 2 〇mg，6mmo 1 )加入一攪拌中 而含有节醒（6 . 11ml ，6〇mmo 1)及4 —甲基 本纸張尺度適用中國國家標準（CNS ) A4規格（210X 297公釐）_ 203 - (請先閱讀背面之注意事項再填寫本頁)1, 1T 524805 A7 B7 printed by the Consumer Cooperatives of the Central Standards Bureau of the Ministry of Economic Affairs 5. Description of the invention (200) —d] Pyridin-7-one was prepared from the title compound of Preparation Example 12 and 3-chloromethylpyridine. It was obtained in the step of 15 B, and it was milk foam (32%). 5 (CDC 1 a): 0.98 (3H, t), 1 · 1 4 (3 Η, t), 1 · 78 (2H5m), 2 · 〇 (2 Η, m), 2 · 9 2 ( 2 Η, t), 4. 1 9 (2 Η, t), 5 · 5 8 (2 Η, s), 7 · 〇 4 (1 Η, d), 7 · 1 4 (1 Η, m), 7.24 (lH ^ m), 7.43 (lH, m), 7.48 (1H, m), 8.40 (1H, d), 8.59 (2H, m), 10.91 (1H, s) . LRMS: m / z 40 (M + 1) +. Preparation Example 2 2 4 — (2-Styryl) Zinc chloride (82 mg, 6 mmo 1) was added to a stirrer to contain awake (6.11 ml, 60 mmo 1) and 4-methyl The basic paper size applies the Chinese National Standard (CNS) A4 specification (210X 297 mm) _ 203-(Please read the precautions on the back before filling this page)

、1T 經濟部中央標準局員工消費合作社印製 524805 A7 B7 五、發明説明（2〇1) 塔哄（2 · 83g，30mmo 1)的混合物裡。在 1 5 0 °C下將混合物加熱2 0小時，冷卻後令其於二氯甲 烷（4 0 m 1 )與2 Μ氫氧化鈉水溶液（2 0 m 1 )之間 分配，把有機相分離出來後與該水相的二氯甲院萃取液（ 8 0 m 1 )合倂，乾燥（N a 2 S〇4 )後減壓蒸發。殘餘 的淺棕色油狀物以管柱層析法利用二氯甲烷：甲醇（9 9 :1 )爲沖提液於矽膠上純化而得呈淺棕色固體之標題化 合物（3 · 6 5 g )。 元素分析實測値：C，7 8 · 9 5 ; Η，5 · 5 2 ; N， 1 5 · 3 9 。C 1 2 Η 1 〇 Ν 2 計算値 C ，7 9 · 1 〇；Η， 5·53;Ν，15.37%。 5 ( C D C 1 a ) :6.96 (lH，d)， 7.45(5H，m)， 7.55(2H，m)， 9 · 1 2 ( 1 H，d )， 9 · 3 0 ( 1 H，s )。 LRMS:m/z 183(M+1)+。 製備例2 3 3 —（·2 —苯乙烯基）嗒哄 由3 —甲基嗒哄依製備例2 2之步驟製得，呈固體（ 5 9%)。 5 ( C D C 1 3 ) :7.12(lH，d)， 7.34(3H，m)， 本紙張尺度適用中國國家標準（CMS ) Α4規格（210X297公釐） •204 - (請先閱讀背面之注意事項再填寫本頁)Printed by the Consumer Cooperative of the Central Standards Bureau of the Ministry of Economic Affairs of the 1T. 524805 A7 B7 V. Description of the invention (201) In the mixture of tower cranes (2.83g, 30mmo 1). The mixture was heated at 150 ° C for 20 hours. After cooling, it was partitioned between dichloromethane (40 m 1) and 2 M aqueous sodium hydroxide solution (20 m 1) to separate the organic phase. It was then combined with the aqueous dichloromethane extract (80 m 1), dried (Na 2 S04), and evaporated under reduced pressure. The residual light brown oil was purified by column chromatography using dichloromethane: methanol (99: 1) as the eluent on silica gel to give the title compound (3.65 g) as a light brown solid. Elemental analysis: 値: C, 7 8 · 9 5; Η, 5 · 5 2; N, 1 5 · 3 9. C 1 2 Η 1 〇 Ν 2 Calculate 値 C, 7 9 · 10; Η, 5.53; N, 15.37%. 5 (C D C 1 a): 6.96 (lH, d), 7.45 (5H, m), 7.55 (2H, m), 9 · 1 2 (1 H, d), 9 · 3 0 (1 H, s). LRMS: m / z 183 (M + 1) +. Preparation Example 2 3 3-(· 2-Styrenyl) Glutathione was prepared from 3 -methyl dimethylsilicone according to the procedure of Preparation 2 2 and was solid (59%). 5 (CDC 1 3): 7.12 (lH, d), 7.34 (3H, m), this paper size applies Chinese National Standard (CMS) A4 specification (210X297 mm) • 204-(Please read the precautions on the back before (Fill in this page)

、1T 丨_ 經濟部中央標準局員工消費合作社印製 524805 A7 B7 '_____ 五、發明説明（2〇2) 7 · 5 6 ( 2 Η，d )， 7 . 7 2 ( 1 Η > d )， 8 · 3 7 ( 1 Η，s )， 8 · 5 〇（1 Η，s )， 8 · 6 0 ( 1 Η，s )。 LRMS :m/z 183 (M+l)+。 製備例2 4 4 一（2 —苯乙烯基）嗒畊 由4 -甲基嘧D定依製備例2 2之步驟製得，呈固體（ 7 7 % ) 〇 5 ( C D C 1 3 ) :7.〇6(lH，d)， 7 · 3 6 ( 4 Η，m )， 7 · 5 8 ( 2 Η，m )， 7 · 9 2 ( 1 Η，d )， 8 · 6 9 ( 1 Η，d )， 9 · 1 4 ( 1 Η，s )。 製備例2 5 4 一羥甲基嗒哄 在一 1 0 °C下將臭氧打入一攪拌中而由製備例2 2標 題化合物（3 · 6〇g ，〇·〇2m〇 1)於甲醇（ 1 5 0 m 1 )中所形成的溶液裡，並令其氣泡透過該溶液 ’ 3 0分鐘後用氮氣淸滌該混合物，接著分批添加硼氫化 (請先閱讀背面之注意事項再填寫本頁}、 1T 丨 _ Printed by the Consumer Cooperatives of the Central Standards Bureau of the Ministry of Economic Affairs 524805 A7 B7 '_____ V. Description of the Invention (2〇2) 7 · 5 6 (2 Η, d), 7. 7 2 (1 Η > d) , 8 · 3 7 (1 Η, s), 8 · 5 〇 (1 8, s), 8 · 6 0 (1 Η, s). LRMS: m / z 183 (M + 1) +. Preparation Example 2 4 4 A (2-styryl) dagen was prepared from 4-methylpyridine D according to the procedure of Preparation Example 2 2 as a solid (77%) 〇5 (CDC 1 3): 7. 〇6 (lH, d), 7 · 3 6 (4 Η, m), 7 · 5 8 (2 Η, m), 7 · 9 2 (1 Η, d), 8 · 6 9 (1 Η, d ), 9 · 1 4 (1 Η, s). Preparation Example 2 5 4 A methylol group was added to a stirring solution at 10 ° C. The title compound (3.60 g, 0.002 mol) from Preparation Example 2 2 was dissolved in methanol ( 1 50 m 1), and let its bubbles pass through the solution '30 minutes later, the mixture was purged with nitrogen, and then borohydride was added in batches (please read the precautions on the back before filling this page) }

本紙張尺度適用中國國家標準（CNS ) A4規格（210X297公釐） -205- 經濟部中央標隼局員工消費合作社印製 524805 A7 B7 五、發明説明（2〇3) 鈉（7 5〇m g，〇 · 〇 2 m ο 1 )，再於室溫下把所得 溶液攪拌2小時。以2 Μ氫氯酸將反應混合物酸化，再用 〇· 8 8 0氨水溶液鹼化之，然後減壓蒸發。以管柱層析 法利用二氯甲烷··甲醇（9 8 ·· 2至9 6 ·· 4 )之沖提梯 度在矽膠上對蒸發殘餘物加以純化而得到呈黃褐色固體之 標題化合物（1 · 6 4 g )。 元素分析實測値：C，5 4 . 2 6 ; Η，5 · 4 2 ; N， 2 5 ·〇 1 。C5H6N2〇計算値 C ，54 · 54 ; Η， 5·49;Ν，25·44%。 ^ ( C D C 1 3 ) :3.12(lH，s)， 4 · 8 2 ( 2 H，s )， 7 · 5 4 ( 1 H，d )， 9 · 1 2 ( 1 H，d )， 9 · 1 6 ( 1 H，s )。 LRMS:m/z 111(M+1)+。 製備例2 6 3 —羥甲基嗒哄 由製備例2 3之標題化合物依製備例2 5之步驟製得 ’呈固體（7 6 % )。 ^ ( C D C 1 3 ) :3.66(lH，s)， 4 · 9 2 ( 2 Η，s )， 7 · 4 8 ( 2 Η，m )， 9 ·〇 6 ( 1 Η，d )。 本紙張尺度適用中國國家標準（CNS ) A4規格（210X 297公釐）-206 - (讀先閱讀背面之注意事項再填寫本頁) ▼This paper size applies to Chinese National Standard (CNS) A4 (210X297 mm) -205- Printed by the Consumer Cooperatives of the Central Standardization Bureau of the Ministry of Economic Affairs 524805 A7 B7 V. Description of the invention (203) Sodium (750 mg 〇2 〇 1), and the resulting solution was stirred at room temperature for 2 hours. The reaction mixture was acidified with 2 M hydrochloric acid, basified with an aqueous solution of 0.888 ammonia, and then evaporated under reduced pressure. Column chromatography was used to purify the evaporation residue on silica gel using a gradient of dichloromethane · methanol (9 8 ·· 2 to 9 6 ·· 4) to give the title compound as a yellow-brown solid (1 · 6 4 g). Elemental analysis: 値: C, 5 4. 2 6; Η, 5 · 4 2; N, 2 5 · 〇 1. C5H6N20 calculates 値 C, 54.54; Η, 5.49; N, 25.44%. ^ (CDC 1 3): 3.12 (lH, s), 4 · 8 2 (2 H, s), 7 · 5 4 (1 H, d), 9 · 1 2 (1 H, d), 9 · 1 6 (1 H, s). LRMS: m / z 111 (M + 1) +. Production Example 2 6 3 -Hydroxymethyl oxamine Coated from the title compound of Production Example 23 according to the procedure of Production Example 25 to obtain a solid (76%). ^ (C D C 1 3): 3.66 (lH, s), 4 · 9 2 (2 Η, s), 7 · 4 8 (2 Η, m), 9 · 〇6 (1 Η, d). This paper size applies Chinese National Standard (CNS) A4 specification (210X 297 mm) -206-(Read the precautions on the back before filling in this page) ▼

'IT 524805 經濟部中央標準局員工消費合作社印製 A7 B7 五、發明説明（2〇4) 製備例2 7 4 —羥甲基嘧啶 由製備例2 4之標題化合物依製備例2 5之步驟製得 ，呈黃色固體（8 3 % )。 5 ( C D C 1 a ) :2.88(lH，s)， 4 · 7 8 ( 2 Η，s )， 7 · 3 6 ( 1 Η，d )， 8 · 7 2 ( 1 Η，d )， 9 · 1 8 ( 1 Η，s )。 製備例2 8 3 —氯甲基嗒哄鹽酸鹽 將硫醯氯（3 · 05ml ，42mmo 1)加入一以 冰冷卻而含有製備例2 6標題化合物（9 2 0 m g，8 m m ◦ 1 )之燒杯裡。在室溫下攪拌該反應混合物4 5分 鐘，然後減壓蒸發。令殘餘物與甲苯（4 0 m 1 )共沸而 得棕色固體之粗製標題化合物（1 . 4 g )，其純度足以 用來產生後續烷化反應所需之自由鹼。 δ ( D M S 0 d 6 ) :4.98(2H，s)， 7 · 8 〇（1 Η，m )， 7 · 9 〇（1 Η，d )， 89 ( 1 Η，s )， 9 · 2 2 ( 1 Η ，d )。 本纸張尺度適用中國國家標準（CNS ) A4規格（210X297公釐）-207 - (請先閱讀背面之注意事項再填寫本頁) _«衣· 訂 經濟部中央標準局員工消費合作社印製 524805 A7 B7 五、發明説明（205) 製備例2 9 3 —乙基一 5 —（2 —正丙氧苯基）一2 —(嗒畊一 3 —基）甲基—2，6 —二氫/— 7H —吼_並〔4，3 — d〕嘧啶—了—酮 由製備例1 3及製備例2 8之標題化合物（其中在製 備例2 8爲自由鹼）依製備例1 5 C之步驟製得，呈泡沬 狀（2 8 % )。 5(CDCl3):1.13(3H，t)， 1 · 3 4 ( 3 Η，t )， 2 ·〇〇（2 Η ， m )， 3 ·〇 8 ( 2 Η，d )， 4 · 1 8 ( 2 Η，t )， 5 · 8 8 ( 2 Η，s )， 7 · 0 4 ( 1 Η，d )， 7 · 1 1 ( 1 Η，m )， 7 · 4 6 ( 3 Η，m )， 8 · 4 〇（1 Η，d )， 9 · 1 5 (.1 Η，d )， l〇.92(lH，s)。 LRMS:m/z 391 (M+l)+。 製備例3〇 5 -（2 -正丙氧苯基）一 3 -正丙基一 2 -（嗒哄 本紙張尺度適用中國國家標準（CNS ) Α4規格（210Χ297公釐）· 208 _ (請先閱讀背面之注意事項再填寫本頁)'IT 524805 A7 B7 printed by the Consumer Cooperatives of the Central Standards Bureau of the Ministry of Economic Affairs 5. Description of the Invention (204) Preparation Example 2 7 4 —Hydroxymethylpyrimidine was prepared from the title compound of Preparation Example 2 4 according to the steps of Preparation Example 2 5 It was obtained as a yellow solid (83%). 5 (CDC 1 a): 2.88 (lH, s), 4 · 7 8 (2 Η, s), 7 · 3 6 (1 Η, d), 8 · 7 2 (1 Η, d), 9 · 1 8 (1 Η, s). Preparation Example 2 8 3-Chloromethyl dimethyl hydrochloride Thiochloride (3.05ml, 42mmo 1) was added to a solution containing the title compound of Preparation Example 2 (920 mg, 8 mm ◦ 1) under ice cooling. In the beaker. The reaction mixture was stirred at room temperature for 45 minutes and then evaporated under reduced pressure. The residue was azeotroped with toluene (40 m 1) to give the crude title compound (1.4 g) as a brown solid, which was pure enough to produce the free base required for the subsequent alkylation reaction. δ (DMS 0 d 6): 4.98 (2H, s), 7. 8 0 (1 Η, m), 7. 9 〇 (1 Η, d), 89 (1 Η, s), 9 · 2 2 ( 1 Η, d). This paper size applies to Chinese National Standard (CNS) A4 (210X297 mm) -207-(Please read the precautions on the back before filling this page) _ «Clothing · Order Printed by the Central Consumers Bureau of the Ministry of Economic Affairs Consumer Cooperatives 524805 A7 B7 V. Description of the invention (205) Preparation example 2 9 3 -Ethyl-5-(2 -n-propoxyphenyl) -2-(Dagen-1 -yl) methyl-2,6 -dihydro / — 7H —Hou—and [4,3 — d] pyrimidine—le—one was prepared from the title compound of Preparation Example 13 and Preparation Example 28 (wherein Preparation Example 28 is a free base) according to the steps of Preparation Example 5 C Obtained as blister-like (28%). 5 (CDCl3): 1.13 (3H, t), 1.34 (3 Η, t), 2.0.0 (2 Η, m), 3.0.08 (2 Η, d), 4.18 ( 2 Η, t), 5 · 8 8 (2 Η, s), 7 · 0 4 (1 Η, d), 7 · 1 1 (1 Η, m), 7 · 4 6 (3 Η, m), 8 · 4〇 (1Η, d), 9 · 15 (.1Η, d), 10.92 (1H, s). LRMS: m / z 391 (M + l) +. Preparation Example 305-(2 -n-propoxyphenyl)-3-n-propyl-2-(the paper size of this paper applies the Chinese National Standard (CNS) A4 specification (210 × 297 mm) · 208 _ (please first (Read the notes on the back and fill out this page)

、1T 524805 A7 B7 _____ 五、發明説明（2〇6) 一 3 —基）甲基—2 ，6 —二氫一 7H —吡唑並〔4，3 一 d〕嘧啶一 7 —酮 由製備例1 2及製備例2 8之標題化合物（其中在製 備例2 8爲自由鹼）依製備例1 5 C之步驟製得，呈乳泡 沬狀（2 5 % )。 5(CDCl3):〇.93(3H，t)， 1 · 1 〇（3 Η，t )， 1 · 7 3 ( 2 Η，m )， 1 · 9 8 ( 2 Η，m )， 2 · 9 9 ( 2 Η，t ), 4 · 1 6 ( 2 Η，t )， 5 · 8 4 ( 2 Η，s )， 7 · 0 0 ( 1 Η，s )， 7·08(1Η，ιώ)， 7 · 4 1 ( 3 Η，m )， 8 · 3 8 ( 1 Η，d )， 9 · 1 2 ( 1 Η，d )， 經濟部中央標率局員工消費合作社印製 (請先閲讀背面之注意事項再填寫本頁) 10.90(1H，s)。 L R Μ S ： m / ζ 4〇5(M+1)+。 製備例3 1 5 —（2 —正丙氧苯基）一 3 —正丙基一 2 -（嗒畊 一 4 —基）甲基—2 ’ 6 — 一*氣一7 Η 一批嗤並〔4 ’ 3 一 d〕嘧啶—7 -酮 本紙張尺度適用中國國家標準（CMS ) A4規格（210'〆297公釐）~. 209 - 524805 A7 B7 經濟部中央標準局員工消費合作社印製 五、發明説明（2〇7) 由製備例1 2及製備例2 5之標題化合物依製備例 1 5 E之步驟製得，呈膠（gUm )狀（1 3 % )。 元素分析實測値：C，6 5 · 1 9 ; Η，5 · 9 9 ; N， 2 〇· 6 9 。C22H24N6〇2計算値 C ，6 5 . 3 3 ; Η，5.98;Ν，2〇·78%。5 ( C D C 1 3 ):〇·99(3Η，ΐ)， 1 · 1 3 ( 3 Η，t )， 1 · 8 5 ( 2 Η，m )， 1 · 9 8 ( 2 Η，m )， 2 · 9 2 ( 2 Η，t )， 4 · 1 5 ( 2 Η，t )， 5 · 7 7 ( 2 Η，s )， 7 · 0 2 ( 1 Η，d )， 7 · 1 2 ( 1 Η，m )， 7 · 3 5 ( 1 Η，d )， 7 · 4 4 ( 1 Η，m )， 8.48(lH，d)， 9 · 1 〇（1 H，d )， 9 · 1 6 ( 1 H，s )， 11.29(lH，s)。 LRMS :m/z 405 (M+l)+。 製備例3 2 5— (2 —正丙氧苯基）一 3 -正丙基一 2 -（嚼u定 (請先閱讀背面之注意事項再填寫本頁) 衣. 、-口1T 524805 A7 B7 _____ V. Description of the invention (20) A 3-yl) methyl-2,6-dihydro-7H-pyrazolo [4,3-d] pyrimidin-7-one Preparation Example 12 and the title compound of Preparation Example 28 (wherein the free base is in Preparation Example 28) were prepared according to the procedure of Preparation Example 15C, and showed the shape of a milk froth (25%). 5 (CDCl3): 0.93 (3H, t), 1 · 1 0 (3 Η, t), 1 · 7 3 (2 Η, m), 1 · 9 8 (2 Η, m), 2 · 9 9 (2 Η, t), 4 · 1 6 (2 Η, t), 5 · 8 4 (2 Η, s), 7 · 0 0 (1 Η, s), 7.08 (1 Η, ιώ), 7 · 4 1 (3 Η, m), 8 · 3 8 (1 Η, d), 9 · 1 2 (1 Η, d), printed by the Consumer Cooperatives of the Central Standards Bureau of the Ministry of Economic Affairs (please read the first Note: Please fill in this page again) 10.90 (1H, s). L R M S: m / ζ 40.5 (M + 1) +. Preparation Example 3 1 5 — (2 —n-propoxyphenyl) —3—n-propyl—2— (daquinone—4-yl) methyl—2 ′ 6—one * gas—7 Η A batch of fluorene and [ 4 '3 a d] Pyrimidine-7-one This paper size is applicable to the Chinese National Standard (CMS) A4 specification (210'〆297 mm) ~. 209-524805 A7 B7 Printed by the Consumer Cooperatives of the Central Standards Bureau of the Ministry of Economic Affairs Description of the invention (207) The title compound of Preparation Example 12 and Preparation Example 5 was prepared according to the procedure of Preparation Example 15E, and was in the form of a gum (gUm) (13%). Elemental analysis: 値: C, 6 5 · 19; Η, 5 · 9 9; N, 2 0.69. C22H24N602 calculates 値 C, 6 5. 3 3; Η, 5.98; N, 20.78%. 5 (CDC 1 3): 0.99 (3 Η, ΐ), 1 · 1 3 (3 Η, t), 1 · 8 5 (2 Η, m), 1 · 9 8 (2 Η, m), 2 · 9 2 (2 Η, t), 4 · 1 5 (2 Η, t), 5 · 7 7 (2 Η, s), 7 · 0 2 (1 Η, d), 7 · 1 2 (1 Η , M), 7 · 3 5 (1 Η, d), 7 · 4 4 (1 Η, m), 8.48 (lH, d), 9 · 1 〇 (1 H, d), 9 · 1 6 (1 H, s), 11.29 (lH, s). LRMS: m / z 405 (M + 1) +. Preparation Example 3 2 5 — (2 —n-propoxyphenyl) — 3 —n-propyl — 2 — (Cheudine (Please read the precautions on the back before filling out this page).

本紙張尺度適用中國國家標準（CNS ) A4規格（210X297公釐）-210 - 經濟部中央標準局員工消費合作社印製 524805 kl B7 五、發明説明（2〇8) —4 一基）甲基—2，6 —二氫一 7H —吡唑並〔4，3 —d〕嘧啶一 7 -酮 由製備例1 2及製備例2 7之標題化合物依製備例 15E之步驟製得，呈白色固體（9%)。 (5 ( C D C 1 3 ):〇.96(3H，t)， 1 · 1 2 ( 3 Η，t )， 1 · 7 6 ( 2 Η，m )， 2.〇0(2H，m)， 2.94(2H，t)， 4 · 1 6 ( 2 H，t )， 5 · 6 1 ( 2 H，s )， 6 · 9 8 ( 1 H，d )， 7 · 0 5 ( 1 H，d )， 7 · 1 〇（1 H，m )， 7.46(lH，m)， 8 · 4 0 ( 1 H，d )， 8 · 6 4 ( 1 H，d·)， 9 · 1 8 ( 1 H，s )， l〇.94(lH，s)。 LRMS:m/z 4〇5(M+1)+。 製備例3 3This paper size applies to China National Standard (CNS) A4 (210X297 mm) -210-Printed by the Consumer Cooperatives of the Central Standards Bureau of the Ministry of Economic Affairs 524805 kl B7 V. Description of the invention (208) -4 1-based) Methyl- 2,6-dihydro-7H-pyrazolo [4,3-d] pyrimidin-7-one was prepared from the title compound of Preparation 12 and Preparation 7 according to the procedure of Preparation 15E as a white solid ( 9%). (5 (CDC 1 3): 0.96 (3H, t), 1 · 1 2 (3 Η, t), 1 · 7 6 (2 Η, m), 2. 〇 (2H, m), 2.94 (2H, t), 4 · 1 6 (2 H, t), 5 · 6 1 (2 H, s), 6 · 9 8 (1 H, d), 7 · 0 5 (1 H, d), 7 · 10 (1 H, m), 7.46 (lH, m), 8 · 4 0 (1 H, d), 8 · 6 4 (1 H, d ·), 9 · 1 8 (1 H, s ), L.94 (lH, s). LRMS: m / z 40 (M + 1) +. Preparation Example 3 3

2 —〔 （2，4 —二氯嘧啶一 5 —基）甲基〕一 5 — (2 -正丙氧苯基）一 3 -正丙基一 2，6 -二氫一 7H 本纸張尺度適用中國國家標準（CNS ) A4規格（210X297公釐）~:211 - (請先閲讀背面之注意事項再填寫本頁) _裝_2 — [(2,4-dichloropyrimidin-5-yl) methyl] -5— (2-n-propoxyphenyl) -3—n-propyl-2,6-dihydro-7H Applicable Chinese National Standard (CNS) A4 specification (210X297mm) ~: 211-(Please read the precautions on the back before filling this page) _ 装 _

、1T 524805 A7 五、發明説明（209) 一吡唑並〔4，3 - d〕嘧啶一 7 —酮 由製備例12之標題化合物及2，4 一二氯一 5 —氯 甲基嘧啶依製備例1 5 B之步驟製得，呈黃色泡線狀（ 4 0%)。 δ ( C D C 1 a ):〇.97(3H，t)， 1 ·〇 7 ( 3 Η，t )， 1 · 8 〇（2 Η，m )， 1 . 9 8 ( 2 Η，m )， 2 · 9 5 ( 2 Η，t )， 4 · 1 4 ( 2 Η，t )， 5 · 5 7 ( 2 Η，s )， 7 · 0 0 ( 1 Η，d )， 7 · 1 0 ( 1 Η，m )， 7 · 4 6 ( 1 Η，m )， 8 · 1 3 ( 1 Η，s )， 8 · 3 9 ( 1 Η，d )， 經濟部中央標準局員工消費合作社印^ (讀先閲讀背面之注意事項再填寫本頁) l〇.95(lH，s) 〇 LRMS:m/z 474 (M+1) +。 製備例3 4 5 — (2 —正丙氧苯基）一 3 —正丙基一 2 -（喃π定 —5 —基）甲基一 2，6 —二氫—7H —吡唑並〔4，3 —d〕嘧D定—7 —酮 將製備例3 3之標題化合物（5 2 3 m g，1 . 1 本紙張尺度適用中國國家標準（CNS ) A4規格（210X297公釐）-212 - 524805 A7 五、發明説明（210) mmo 1)加入由三乙胺（3 · 0ml ，21 · 5 m m ο 1 )於乙醇（2 5 m 1 )中所形成的溶液裡，然後 添加10%鈀（於木炭上，150mg)，令混合物於 2 7 6 k P a ( 4 0 p s i )及室溫下氫化1小時，然後 過濾。將濾液與濾片的乙醇洗液（5 0 m 1 )合倂，然後 減壓蒸發。將殘餘物懸浮於水（1 5 m 1 )中，再以乙酸 乙酯（5 0 m 1 )對該混合物進行萃取。萃取液經乾燥（ N a 2 S〇4 )後減壓濃縮。殘餘物以管柱層析法利用二氯 甲烷：甲醇（9 8 : 2 )爲沖提液在矽膠上純化而得到乳 泡沬狀之標題化合物（2 4 3 m g )。 5 ( C D C 1 3 ) :0.96(3H，t)， 1 ·〇 6 ( 3 Η ， t )， (請先閱讀背面之注意事項再填寫本頁)1T 524805 A7 V. Description of the invention (209) Monopyrazolo [4,3-d] pyrimidin-7-one was prepared from the title compound of Preparation Example 12 and 2,4-dichloro-5-chloromethylpyrimidine It was prepared by the procedure of Example 5B, and it was yellow bubble line (40%). δ (CDC 1 a): 0.97 (3H, t), 1.07 (3 μm, t), 1.8 μ (2 μm, m), 1.98 (2 μm, m), 2 · 9 5 (2 Η, t), 4 · 1 4 (2 Η, t), 5 · 5 7 (2 Η, s), 7 · 0 0 (1 Η, d), 7 · 1 0 (1 Η , M), 7 · 4 6 (1 Η, m), 8 · 1 3 (1 Η, s), 8 · 3 9 (1 Η, d), printed by the Consumer Cooperatives of the Central Standards Bureau of the Ministry of Economic Affairs ^ (read first Read the notes on the back and fill out this page) l 0.95 (lH, s) 〇LRMS: m / z 474 (M + 1) +. Preparation Example 3 4 5 — (2-n-propoxyphenyl) -3-n-propyl-2— (n-pyridin-5-yl) methyl—2,6-dihydro-7H —pyrazolo [4 , 3-d] pyrimidin-7-one The title compound of Preparation 3 3 (5 2 3 mg, 1.1) This paper size applies the Chinese National Standard (CNS) A4 specification (210X297 mm) -212-524805 A7 V. Description of the invention (210) mmo 1) Add the solution formed by triethylamine (3.0 ml, 21.5 mm ο 1) in ethanol (2.5 m 1), and then add 10% palladium (in Charcoal, 150 mg), the mixture was hydrogenated at 276 kPa (40 psi) for 1 hour at room temperature, and then filtered. The filtrate was combined with an ethanol washing solution (50 m 1) of the filter, and then evaporated under reduced pressure. The residue was suspended in water (15 m 1), and the mixture was extracted with ethyl acetate (50 m 1). The extract was dried (Na 2 S04) and concentrated under reduced pressure. The residue was purified by column chromatography using dichloromethane: methanol (98: 2) as the eluent on silica gel to give the title compound (2.33 mg) as a creamer. 5 (C D C 1 3): 0.96 (3H, t), 1 · 〇6 (3 Η, t), (Please read the precautions on the back before filling this page)

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H s -213- 本紙張尺度適用中國國家標準（CMS ) Α4規格（210X297公釐） 524805 A7 B7 經濟部中央標隼局員工消費合作社印製 五、發明説明（211) LRMS:m/z 4〇5(M+1)+。 製備例3 5 3 —乙基一 5 —（2 —正丙氧本基）一 2 —（吼啡— 2 —基）甲基一2，6 -二氫—7H — d比d坐並〔4，3 — d〕嘧啶一 7 -酮 由製備.例1 3之標題化合物及2 —氯甲基吡畊（1· 〇rg. Chem·，1 973，11，2049 )依製備例1 5 B之步驟製得 ，呈泡沬狀（4 6 % )。 (5 ( C D C 1 3 ) :l.〇8(3H，t)， 1 · 3 4 ( 3 Η，t )， 1 . 9 6 ( 2 Η，t )， 3 · Ο 6 ( 2 Η，q )， 4 · 1 4 ( 2 Η，t )， 5 · 6 6 ( 2 Η，s )， 7 · Ο 〇（1 Η，d )， 7 · Ο 8 ( 1 Η，m )， 7.42(lH，m)， 8.37 (lH，d)， 8 · 4 6 ( 1 Η，s )， 8 · 5 Ο ( 2 Η，s )， 1〇.84(1H，s)。 L R Μ S ： m / ζ 391(M+1) +。 (讀先閲讀背面之注意事項再填寫本頁) #·H s -213- This paper size applies Chinese National Standard (CMS) A4 specification (210X297 mm) 524805 A7 B7 Printed by the Consumer Cooperatives of the Central Bureau of Standards of the Ministry of Economic Affairs 5. Description of invention (211) LRMS: m / z 4〇 5 (M + 1) +. Preparation Example 3 5 3 —Ethyl-5— (2-n-propoxybenzyl) —2— (Cryphin-2-yl) methyl—2,6-dihydro-7H — d sits and d [4 3, d] pyrimidin-7-one was prepared from the title compound of Example 13 and 2-chloromethylpyracine (1.0 rg. Chem., 1 973, 11, 2049) according to Preparation Example 5 B It was prepared in the steps and was bubble-like (46%). (5 (CDC 1 3): 1.08 (3H, t), 1. 3 4 (3 Η, t), 1. 9 6 (2 Η, t), 3. Ο 6 (2 Η, q) , 4 · 1 4 (2 Η, t), 5 · 6 6 (2 Η, s), 7 · 〇 〇 (1 Η, d), 7 · 〇 8 (1 Η, m), 7.42 (lH, m ), 8.37 (lH, d), 8.46 (1 (, s), 8.50 (2 Η, s), 10.84 (1H, s). LR M S: m / ζ 391 ( M + 1) +. (Read the precautions on the back before filling this page) # ·

*1T 本紙張尺度適用中國國家標準（CNS ) A4規格（210X297公釐）_ 214 - 524805 B7 五、發明説明（212) 製備例3 6 5 — (2 —正丙氧苯基）一 3 -正丙基一 2 -（吡哄 —2 —基）甲基—2，6 -二氫一7H —吡唑並〔4，3 —d〕嘧啶一 7 -酮 由製備例1 2之標題化合物及及2 -氯甲基吡哄（J. 〇rg. Chem·，1 973，11，2049 )依製備例1 5 B之步驟製得 ，呈乳泡沬狀（2 5 % )。 5 ( C D C 1 3 ):〇.97(3H，t)， 1 ·〇 8 ( 3 Η，t )， 1 · 7 8 ( 2 Η，m )， 1 · 9 8 ( 2 Η，m )， 2.99 (2H，t)， 4 · 1 6 ( 2 Η，t )， 5 · 6 6 ( 2 Η，s )， 7 · 0 1 ( 1 Η，d )， 7 · 1 0 ( 1 Η，m )， 7 · 4 1 ( 1 Η，m )， 經濟部中央標隼局員工消費合作社印製 (請先閱讀背面之注意事項再填寫本頁} 8 · 3 9 ( 1 Η，d )， 8 · 4 4 ( 1 Η，s )， 8 · 5 〇（2 Η，s )， 10.85(lH，s)。 LRMS:m/z 405 (M+1) +。 製備例3 7 本纸張尺度適用中國國家標準（CNS ) A4規格（210X 297公釐） 524805 A7 B7 五、發明説明（213) 4 一（2 —乙氧苄醯胺基）一3 —甲基一 1H —吡唑 一 5 —甲醯胺 由4 —胺基一 3 —甲基一1H —吡唑一5 —甲醯胺（ J.〇rg.. C hem.，1956，U，833)及2 —乙氧苄醯氯以製備 例9之類似方式製得，呈白色粉末（8 3 % )。 5 ( D M S 0 d 6 ) ： 1 . 4 4 ( 3 Η > t )， 2 . 2 8 ( 3 Η，s )， 4 · 2 8 ( 2 Η，q )， 7 · 0 6 ( 1 Η，m )， 7 · 1 9 ( 2 Η，m )， 7 · 4 8 ( 2 Η，m )， 8 ·〇〇（1 Η ， d )， l〇.46(lH，s)， 12.88(lH，s) ° LRMS:m/z 28 9 (M+1)+。 製備例3 8 經濟部中央標準局員工消費合作社印製 (讀先閱讀背面之注意事項再填寫本頁) 4 — (2 —甲氧苄醯胺基）一 3 —正丙基一 1H —吡 唑一 5 —甲醯胺 由製備例7之標題化合物及2 -甲氧苄醯氯依製備例 9之類似方式製得，呈白色粉末（5 5%)。 5 ( D M S 0 d 6 ):〇·84(3Η，ΐ)， 1 · 5 5 ( 2 Η，m )， 2 · 7 9 ( 2 Η，t )， 本紙張尺度適用中國國家標準（CNS ) Α4規格（21 ΟΧ 297公釐）_ 216 _ 524805 A7 B7 經濟部中央標準局員工消費合作社印製 五 、發明説明（ 214) 1 I 4 • 〇 〇 ( 3 Η S ) 1 I 7 • 〇 8 ( 1 Η m ) 1 1 I 7 2 〇 ( 1 Η d ) 1 I 請 1 I 7 2 8 ( 1 Η s ) 先 閲 1 I 讀 1 | 7 . 4 4 ( 1 Η s ) 背 1 I 1 7 . 5 4 ( 1 Η m ) 1 I /公 事 1 1 〇 • 6 2 ( 1 Η s ) ο 項 再 1 L R Μ S ； m / ζ 3 〇 3 ( Μ + 1 ) + 〇 填 寫 頁 1 I 製 備 例 3 9 1 1 1 5 — ( 2 — 乙 氧 苯 基 ) — 3 — 甲 基 — 1， 6 -二 氫一 1 I 7 Η — 吡 唑 並 ( 4 > 3 — d ] 嘧 Β定 — 7 — 酮 1 訂 | 由 製 備 例 3 7 之 標 題 化 合 物 以 製 備 例 12 之 類似 方式 1 1 I 製 得 呈 白 色 固 體 ( 9 2 % ) ο 1 1 (5 ( D Μ S 〇 d 6 -) : 1 . 3 〇 ( 3 Η t )， 1 1 2 • 4 〇 ( 3 Η s ) 5 • I 4 • 1 2 ( 2 Η Q ) 1 1 1 7 • 〇 5 ( 1 Η > m ) > 1 1 7 • 1 4 ( 1 Η d ) ， 1 1 7 • 4 6 ( 1 Η ， m ) 1 | 7 • 6 8 ( 1 Η 5 d ) 1 I 1 1 • 9 〇 ( 1 Η ， s ) 5 1 1 1 3 • 6 8 ( 1 Η j s ) Ο 1 1 L R Μ S m / ζ 2 7 1 ( Μ + 1 ) + 〇 1 1 1 本紙張尺度適用中國國家標準（CNS ) A4規格（210X297公釐）-217 - 524805 經濟、郅中央榡隼局員工消費合作杜印製 A7 B7 五、發明説明（215) 製備例4〇 5 —（2 —甲氧苯基）一 3 —正丙基一 1 ，6 一二氫 〜7 Η —吡唑並〔4 ’ 3 — d〕嘧u定一 7 一酮 由製備例3 8之標題化合物以製備例1 2之類似方式 製得，呈白色固體（71%)。 5(DMS〇d6):0.92(3H，t)， 1 · 7 6 ( 2 Η，m )， 2 · 8 Ο ( 2 Η，t )， 3 · 8 5 ( 3 Η，s )， 7 · 〇 8 ( 1 Η，m )， 7 · 1 7 ( 1 Η，d )， 7 · 4 9 ( 1 Η，m )， 7 · 6 4 ( 1 Η，d )， 11.47— 11.94(lH，br)， 13·69 — 13.94(lH’br)。 L R Μ S ： m / z 285(M+1) +。 製備例4 1 5 — (2 —甲氧苯基）—3 —正丙基一 1 一（吡啶一 2 —基）甲基一 1，6 —二氫一 7H —吡唑並〔4，3 — d〕嘧啶—7 -酮 由製備例4 0之標題化合物及2 -氯甲基吡啶依製備 例1 5 D之步驟製得，呈白色晶狀固體（3 8 % )。 本紙張尺度適用中國國家標準（CNS ) A4規格（21〇>< 297公釐）-218 - (請先閲讀背面之注意事項再填寫本頁)* 1T This paper size is in accordance with Chinese National Standard (CNS) A4 specification (210X297 mm) _ 214-524805 B7 V. Description of the invention (212) Preparation example 3 6 5 — (2 —n-propoxyphenyl) —3—n Propyl-2- (pyridine-2-yl) methyl-2,6-dihydro-7H-pyrazolo [4,3-d] pyrimidin-7-one was prepared from the title compound of Preparation Example 12 and and 2-Chloromethylpyridine (J. Org. Chem., 1 973, 11, 2049) was prepared according to the procedure of Preparation Example 15B, and it appeared as a milky bubble (25%). 5 (CDC 1 3): 0.97 (3H, t), 1.08 (3 Η, t), 1.7.8 (2 Η, m), 1.98 (2 Η, m), 2.99 (2H, t), 4 · 1 6 (2 Η, t), 5 · 6 6 (2 Η, s), 7 · 0 1 (1 Η, d), 7 · 1 0 (1 Η, m), 7 · 4 1 (1 Η, m), printed by the Consumer Cooperatives of the Central Bureau of Standards, Ministry of Economic Affairs (please read the notes on the back before filling out this page) 8 · 3 9 (1 Η, d), 8 · 4 4 (1 Η, s), 8 · 5 〇 (2 Η, s), 10.85 (lH, s). LRMS: m / z 405 (M + 1) +. Preparation Example 3 7 This paper scale applies Chinese national standard (CNS) A4 specifications (210X 297 mm) 524805 A7 B7 V. Description of the invention (213) 4-(2-ethoxybenzylamino)-3-methyl-1H-pyrazole-5-formamide 4-amino-3-methyl-1H-pyrazole-5-methylamidine (J. Org .. C hem., 1956, U, 833) and 2-ethoxybenzyl chloride to prepare Example 9 Prepared in a similar manner as a white powder (83%). 5 (DMS 0 d 6): 1. 4 4 (3 Η > t), 2. 2 8 (3 Η, s), 4 · 2 8 ( 2 Η, q), 7 · 0 6 (1 Η, m), 7 · 19 (2 Η, m), 7 · 4 8 (2 Η, m), 8 · 〇 (1 Η, d), 10.46 (lH, s), 12.88 (lH, s) ° LRMS : m / z 28 9 (M + 1) +. Preparation Example 3 8 Printed by the Consumer Cooperatives of the Central Bureau of Standards of the Ministry of Economic Affairs (Read the precautions on the back before filling this page) 4 — (2 — Methobenzamine A) 3 -n-propyl-1H -pyrazole-5 -methanamine was prepared from the title compound of Preparation 7 and 2-methoxybenzylchloromethane in a similar manner to Preparation 9 as a white powder (5 5 %). 5 (DMS 0 d 6): 0.84 (3Η, ΐ), 1.55 (2 Η, m), 2 · 7 9 (2 Η, t), and this paper size applies Chinese national standards ( CNS) A4 specification (21 〇 × 297 mm) _ 216 _ 524805 A7 B7 Printed by the Consumer Cooperatives of the Central Standards Bureau of the Ministry of Economic Affairs V. Invention Description (214) 1 I 4 • 〇〇 (3 Η S) 1 I 7 • 〇 8 (1 Η m) 1 1 I 7 2 〇 (1 Η d) 1 I Please 1 I 7 2 8 (1 Η s) Read first 1 I Read 1 | 7. 4 4 (1 Η s) Back 1 I 1 7. 5 4 (1 Η m) 1 I / business 1 1 〇 • 6 2 (1 Η s) ο item and then 1 LR MS; m / ζ 3 〇3 (Μ + 1) + 〇 fill in Page 1 I Preparation Example 3 9 1 1 1 5 — (2 —ethoxyphenyl) — 3 —methyl — 1, 6 -dihydro-1 1 7 —pyrazolo (4 > 3 — d] pyrimido Β 定 — 7 — ketone 1 order | From the title compound of Preparation Example 3 7 in a similar manner as in Preparation Example 1 1 I to give a white solid (9 2%) ο 1 1 (5 (DM S 〇d 6- ): 1.3 〇 (3 Η t), 1 1 2 • 4 〇 (3 Η s) 5 • I 4 • 1 2 (2 Η Q) 1 1 1 7 • 〇5 (1 Η > m) > 1 1 7 • 1 4 (1 Η d), 1 1 7 • 4 6 (1 Η, m) 1 | 7 • 6 8 (1 Η 5 d) 1 I 1 1 • 9 〇 (1 Η, s) 5 1 1 1 3 • 6 8 (1 Η js) 1 1 LR Μ S m / ζ 2 7 1 (Μ + 1) + 〇1 1 1 This paper size is applicable to China National Standard (CNS) A4 specification (210X297 mm) -217-524805 Economy, Central Government Bureau employees Consumption cooperation Du printed A7 B7 V. Description of the invention (215) Preparation example 4 05 — (2-methoxyphenyl) — 3 —n-propyl — 1, 6 —dihydro ~ 7 Η —pyrazolo [4 '3-d] pyrimidin-7 monoone was prepared from the title compound of Preparation Example 38 in a similar manner to Preparation Example 12 as a white solid (71%). 5 (DMS〇d6): 0.92 (3H, t), 1 · 7 6 (2 Η, m), 2 · 8 〇 (2 Η, t), 3 · 8 5 (3 Η, s), 7 · 〇 8 (1 Η, m), 7 · 1 7 (1 Η, d), 7 · 4 9 (1 Η, m), 7 · 6 4 (1 Η, d), 11.47— 11.94 (lH, br), 13.69 — 13.94 (lH'br). L R MS: m / z 285 (M + 1) +. Production Example 4 1 5 — (2-Methoxyphenyl) — 3 —n-propyl — 1 — (pyridine — 2 —yl) methyl — 1, 6 —dihydro — 7H — pyrazolo [4, 3 — d] Pyrimidin-7-one was prepared from the title compound of Preparation Example 40 and 2-chloromethylpyridine according to the procedure of Preparation Example 15D, and a white crystalline solid (38%). This paper size applies Chinese National Standard (CNS) A4 specification (21〇 > < 297mm) -218-(Please read the precautions on the back before filling this page)

524805 經濟部中央標準局員工消費合作社印製 A7 B7 五、發明説明（216) 元素分析實測値：C ，6 7 ·〇〇；Η，5 · 6〇；N， 18 · 4 9。C21H21N5〇2計算値 C，67 · 18 ； Η，5·64;Ν，18.65%。 5 ( C D C 1 a ) :l.〇l(3H，t)， 1 · 9 0 ( 2 Η，m )， 2 . 9 8 ( 2 Η，t )， 4 ·〇 3 ( 3 Η，s )， 5 · 9 6 ( 2 Η，s )， 6 · 9 9 ( 1 Η，d )， 7 ·〇 5 ( 1 Η，d )， 7 . 1 6 ( 2 Η，m )， 7 · 4 7 ( 1 Η，m )， 7 · 5 9 ( 1 Η，m )， 8 · 4 8 ( 1 Η，d )， 8 · 5 8 ( 1 Η，d )， l〇.88(lH，s)° 製備例4 2 5 —（2 —乙氧苯基）一 3 —甲基一 2 —（吡啶一 2 一基）甲基一 2，6 —二氫—7H — d比哩並〔4，3 — d 〕嘧啶一 7 —酮 由製備例3 9之標題化合物及2 -氯甲基吡啶依製備 例1 5 B之步驟製得，呈白色泡沬狀（2 1 % )。 元素分析實測値：C，6 5 · 3〇；Η，5 · 0 8 ; N， 本紙張尺度適用中國國家標準（CNS ) Α4規格（210X 297公釐）-219 - (讀先閱讀背面之注意事項再填寫本頁) 訂 經濟部中央標準局員工消費合作社印製 524805 A7 五、發明説明（217) 18 · 79 。C2〇H19N5〇2;〇· 3〇1"12〇計算値〇 ，65·49;Η，5·.3 9;Ν，19·〇9%。 5(CDCl3):1.59(3H，t)， 2 · 5 7 ( 3 Η，s )， 4 · 2 8 ( 2 Η，Q )， 5 · 6 6 ( 2 Η，s )， 7 ·〇 8 ( 3 Η，m )， 7 · 2 〇（1 Η，m )， 7 · 4 4 ( 1 Η，m )， 7 · 6 2 ( 1 Η，m )， 8 · 4 2 ( 1 Η，d )， 8 · 5 9 ( 1 Η，d )， 10.88(lH，s)° L R M S ： m / z 362(M+1)+。 製備例4 3 5— (2 —甲氧苯基）一3 —正丙基一 2 —(吡啶一 2 —基）甲基一2，6 —二氫一7H —吼哩並〔4，3 — d〕嘧啶一 7 -酮 由製備例4 0之標題化合物及2 -氯甲基吡啶依製備 例1 5 B之步驟製得，呈白色晶狀固體。 元素分析實測値：C，6 6 · 9 3 ; Η，5 · 6 1 ; N， 18 · 61。C21H21N5〇2計算値 C，67 · 18 ; H，5.64 ;N，18.65%。 本紙張尺度適用中國國家標準（CNS ) A4規格（210X297公釐）_ 220 - (讀先閱讀背面之注意事項再填寫本頁) 訂 524805 A7 B7 五、發明説明（218) ά ( C D C 1 a ):〇.96(3H，t)， 1 · 7 6 ( 2 Η，m )， 2 · 9 8 ( 2 Η，t )， 4 · Ο 3 ( 3 Η，s )， 5 · 6 8 ( 2 Η，s )， 7.〇5(2H，2xd)， 7 · 1 6 ( 1 Η，m )， 7 · 2 1 ( 1 Η，m )， 7 · 4 6 ( 1 Η，m )， 7 · 6 2 ( 1 Η，m )， 8 · 4 1 ( 1 Η，d )， 8 · 5 8 ( 1 Η，d )， 10.78(lH，s)。 LRMS:m/z 376 (M+1)+。 製備例4 4 經濟部中央標隼局員工消費合作社印製 (讀先閲讀背面之注意事項再填寫本頁) 5 —〔5 —（4 一第三丁氧羰基六氫吡畊—1—基磺 醯基）一 2 -正丙氧苯基〕一 3 -正丙基一 2 -（吡啶一 2 —基）甲基一 2，6 —二氫一 7H -吡唑並〔4，3 — d〕嘧啶—7 —酮 由製備例2 0之標題化合物及1 -第三丁氧羰基六氫 吡哄依實施例1之步驟製得，呈固體（6 0 % )。 δ ( C D C 1 a ) ： 0 . 9 6 ( 3 H ^ t )， 1 · 1 5 ( 3 Η ， t )， 本紙張尺度適用中國國家標準（CMS ) A4規格（210X 297公釐）-221 - 經濟部中央標準局員工消費合作社印製 524805 A7 B7 五、發明説明（219) 1 · 4 〇（9 Η，s )， 1 · 7 6 ( 2 Η，m )， 2 · 0 4 ( 2 Η，m )， 2 · 9 8 ( 2 Η，t )， 3 ·〇 3 ( 4 Η，m )， 3 . 5 2 ( 4 Η，m )， 4 . 2 6 ( 2 H ^ t )， 5 · 7 0 ( 2 H，s )， 7 · 0 6 ( 1 Ή，m )， 7 · 1 6 ( 1 H，d )， 7 · 2 1 ( 1 H，m )， 7.62(lH，m)， 7 · 8 2 ( 1 H，d )， 8 · 5 8 ( 1 H，d )， 8 · 7 8 ( 1 H，s )， 10.60(lH，s)。 LRMS:m/z 652(M+1)+。 製備例4 5 3 —甲氧一 2 —甲基吡啶 將一攪拌中而含有3 —羥—2 —甲基吡啶（1 . 0 g ，9 · 2mmo 1)，溴化苯基三甲基銨（2 . 2g， 11mm〇1)，甲氧化鈉（55〇mg， 11mm〇1 )及二甲基甲醯胺（1 〇 m 1 )之溶液加熱迴流3小時， 本紙張尺度適用中國國家標準（CNS ) Α4規格（210X 297公釐） (讀先閱讀背面之注意事項再填寫本頁) ·衣·524805 Printed by the Consumer Cooperatives of the Central Bureau of Standards of the Ministry of Economic Affairs A7 B7 V. Description of the Invention (216) Elemental analysis and actual measurement: C, 6 7 · 〇; Η, 5 · 60; N, 18 · 49. C21H21N502 Calculates 値 C, 67 · 18; Η, 5.64; N, 18.65%. 5 (CDC 1 a): 1.01 (3H, t), 1.90 (2 Η, m), 2.98 (2 Η, t), 4.03 (3 s, s), 5 · 9 6 (2 Η, s), 6 · 9 9 (1 Η, d), 7 · 05 (1 Η, d), 7. 1 6 (2 Η, m), 7 · 4 7 (1 Η, m), 7 · 5 9 (1 Η, m), 8 · 4 8 (1 Η, d), 8 · 5 8 (1 Η, d), 10.88 (lH, s) ° Preparation Example 4 2 5 — (2-ethoxyphenyl) —3-methyl—2— (pyridine—2—yl) —methyl—2,6-dihydro—7H — d specific mile [4,3 — d] Pyrimidine-7-one was prepared from the title compound of Preparation Example 39 and 2-chloromethylpyridine according to the procedure of Preparation Example 15B, and was white foamy (21%). Elemental analysis: 値: C, 6 5 · 30; Η, 5 · 0 8; N, This paper size is applicable to China National Standard (CNS) Α4 specification (210X 297 mm) -219-(Read the note on the back before reading Please fill in this page again for the matters) Order printed by the Consumers Cooperative of the Central Standards Bureau of the Ministry of Economic Affairs 524805 A7 V. Invention Description (217) 18 · 79. C20H19N502; 0.301 " 120 calculation 値 〇, 65.49; Η, 5. · 3 9; N, 19.09%. 5 (CDCl3): 1.59 (3H, t), 2 · 5 7 (3 Η, s), 4 · 2 8 (2 Η, Q), 5 · 6 6 (2 Η, s), 7 · 〇8 ( 3 Η, m), 7 · 2 0 (1 Η, m), 7 · 4 4 (1 Η, m), 7 · 6 2 (1 Η, m), 8 · 4 2 (1 Η, d), 8 · 5 9 (1 Η, d), 10.88 (lH, s) ° LRMS: m / z 362 (M + 1) +. Production Example 4 3 5— (2-Methoxyphenyl) —3—n-propyl—2— (pyridine—2—yl) methyl—2,6—dihydro—7H— d] Pyrimidine-7-one was prepared from the title compound of Preparation Example 40 and 2-chloromethylpyridine according to the procedure of Preparation Example 15B, and a white crystalline solid. Elemental analysis: 値: C, 6 6 · 9 3;;, 5 · 6 1; N, 18 · 61. C21H21N502 is calculated as C, 67.18; H, 5.64; N, 18.65%. This paper size applies the Chinese National Standard (CNS) A4 specification (210X297 mm) _ 220-(Read the precautions on the back before filling this page) Order 524805 A7 B7 V. Description of the invention (218) ά (CDC 1 a) : 0.96 (3H, t), 1 · 7 6 (2 Η, m), 2 · 9 8 (2 Η, t), 4 · Ο 3 (3 ，, s), 5 · 6 8 (2 Η , S), 7.05 (2H, 2xd), 7 · 16 (1 Η, m), 7 · 2 1 (1 Η, m), 7 · 4 6 (1 Η, m), 7 · 6 2 (1 Η, m), 8 · 4 1 (1 Η, d), 8 · 5 8 (1 Η, d), 10.78 (lH, s). LRMS: m / z 376 (M + 1) +. Preparation Example 4 4 Printed by the Consumer Cooperatives of the Central Bureau of Standards of the Ministry of Economic Affairs (Read the precautions on the back before filling this page) Fluorenyl)-2 -n-propoxyphenyl]-3-n-propyl-2-(pyridine-2 -yl) methyl-2, 6-dihydro-7H-pyrazolo [4, 3 — d] Pyrimidine-7-one was prepared from the title compound of Preparation Example 20 and 1-third butoxycarbonyl hexahydropyridine according to the procedure of Example 1, and was solid (60%). δ (CDC 1 a): 0.96 (3 H ^ t), 1 · 1 5 (3 Η, t), this paper size applies Chinese National Standard (CMS) A4 specification (210X 297 mm) -221- Printed by the Consumer Cooperatives of the Central Standards Bureau of the Ministry of Economic Affairs 524805 A7 B7 V. Description of Invention (219) 1 · 4 0 (9 Η, s), 1 · 7 6 (2 2, m), 2 · 0 4 (2 Η, m), 2 · 9 8 (2 Η, t), 3 · 03 (4 Η, m), 3.5 2 (4 Η, m), 4. 2 6 (2 H ^ t), 5 · 7 0 (2 H, s), 7 · 0 6 (1 Ή, m), 7 · 1 6 (1 H, d), 7 · 2 1 (1 H, m), 7.62 (lH, m), 7 · 8 2 (1 H, d), 8 · 5 8 (1 H, d), 8 · 7 8 (1 H, s), 10.60 (1 H, s). LRMS: m / z 652 (M + 1) +. Preparation Example 4 5 3-Methoxy-2-methylpyridine Agitated to contain 3-hydroxy-2-methylpyridine (1.0 g, 9.2 mmo 1), phenyltrimethylammonium bromide ( A solution of 2.2 g, 11 mm 0), sodium methoxide (55 mg, 11 mm 0) and dimethylformamide (100 ml 1) was heated under reflux for 3 hours. ) Α4 size (210X 297 mm) (Read the precautions on the back before filling in this page) · Clothing ·

、1T 524805 A7 B7 經濟部中央標準局員工消費合作社印製 五、發明説明（220) 冷卻後以水（4〇ml)洗之，再用乙醚（3x40ml )萃取。萃取液合倂後乾燥（N a 2 S〇4 )，減壓蒸發， 然後以管柱層析法利用己烷：乙酸乙酯（1 ·· 1 )爲沖提 液於矽膠上純化而得固態標題化合物（1 9 0 m g )。5 ( C D C 1 a ) :2.34(3H，s)， 3 · 6 8 ( 3 Η，s )， 6 · 9 3 ( 2 Η，m )， 7 · 9 4 ( 1 Η，d )。 LRMS:m/z 124(M+1)+。 製備例4 6 2 —氯甲基一3 —甲氧吡啶 將製備例4 5之標題化合物（1 9 0 m g，1 · 5 mmo 1 )加入一攪拌中而由苄醯胺（5mg，〇 · 4 m m ο 1 )於二氯甲烷（2 m 1 )中所形成的溶液裡，加 熱至迴流溫度。把三氯異三聚氰酸（1 9 Omg， 0 · 8 2 m m ο 1 )分批加入，然後將反應混合物加熱迴 流3小時。冷卻後用水（2 m 1 )及5 0 %氫氧化鉀水溶 液（3 m 1 )處理之，水相分離出來後用二氯甲烷（3 X 1〇m 1 )洗過，有機溶液經合倂，乾燥（N a 2 S〇4 ) ，及減壓蒸發而得到無色油狀的標題化合物（1 8 0 m g )°5 ( C D C 1 3 ) :3.91 (3H，s)，4.76(2H，s)， (請先閱讀背面之注意事項再填寫本頁) 衣·1T 524805 A7 B7 Printed by the Consumer Cooperatives of the Central Standards Bureau of the Ministry of Economic Affairs 5. Description of the invention (220) After cooling, wash with water (40 ml), and then extract with ether (3x40 ml). The extract was combined and dried (N a 2 S04), evaporated under reduced pressure, and then purified by column chromatography using hexane: ethyl acetate (1 ·· 1) as the eluent on silica gel to obtain a solid. The title compound (190 mg). 5 (C D C 1 a): 2.34 (3H, s), 3 · 6 8 (3 Η, s), 6 · 9 3 (2 Η, m), 7 · 9 4 (1 Η, d). LRMS: m / z 124 (M + 1) +. Preparation Example 4 6 2 -chloromethyl-3 -methoxypyridine The title compound of Preparation Example 4 (190 mg, 1.5 mmo 1) was added to a stirring solution, and benzamidine (5 mg, 0.4 mm ο 1) in a solution formed in dichloromethane (2 m 1) and heated to reflux temperature. Trichloroisotricyanic acid (190 mg, 0.82 mm 0) was added in portions, and the reaction mixture was heated to reflux for 3 hours. After cooling, it was treated with water (2 m 1) and 50% aqueous potassium hydroxide solution (3 m 1). After the water phase was separated, it was washed with dichloromethane (3 X 10 m 1). The organic solution was combined, Dry (N a 2 S04) and evaporate under reduced pressure to give the title compound (180 mg) ° 5 (CDC 1 3): 3.91 (3H, s), 4.76 (2H, s), (Please read the precautions on the back before filling this page)

、1T, 1T

本紙張尺度適用中國國家標準（CNS ) Α4規格（210X297公釐）-223 - 524805 經濟部中央標準局員工消費合作社印製 kl 五、發明説明（221) 7 · 2 5 ( 2 Η，m )， 8 · 2 0 ( 1 Η，d )。 L R M S ： m / z 158(M+1)+。 製備例4 7 1— (3 —甲氧哦陡一2 —基）甲基一5 — (2 —正 丙氧苯基）一 3 —正丙氧苯基）一 3 —正丙基一 1 ，6 — 二氫一 7 Η -吡唑並〔4，3 — d〕嘧啶一 7 —酮 由製備例1 2及製備例4 6之標題化合物依製備例 15B之步驟製得，呈白色固體（4%)。 5 ( C D C 1 3 ) :0.98(3H，t)， 1 · 1 2 ( 3 Η，t )， 1 · 8 3 ( 2 Η，m )， 1 · 9 7 ( 2 Η，m )， 2 · 9 2 ( 2 Η，t )， 3.80(3H，s)， 4 · 1 6 ( 2 Η，t )， 5 · 9 6 ( 2 Η，s )， 7 · 0 〇（1 Η，d )， 7 · 1 0 ( 3 Η，m )， 7 · 4 1 ( 1 Η，m )， 8 ·〇 1 ( 1 Η，d )， 8 · 4 8 ( 1 Η，d )， ll.〇8(lH，s)° 本紙張尺度適用中國國家標準（CNS ) A4規格（210X297公釐)~- 224 - (請先閲讀背面之注意事項再填寫本頁) —0 .項再填· 裝·This paper size applies to Chinese National Standard (CNS) A4 specification (210X297 mm) -223-524805 Printed by the Consumer Cooperatives of the Central Standards Bureau, Ministry of Economic Affairs, Kl. 5. Description of the invention (221) 7 · 2 5 (2 Η, m), 8 · 2 0 (1 Η, d). L R M S: m / z 158 (M + 1) +. Preparation Example 4 7 1— (3-Methoxy-Oxy-2-yl) methyl—5— (2-N-propoxyphenyl) —3—N-propoxyphenyl) —3—N-propyl-1, 6-Dihydro-7 hydrazone-pyrazolo [4,3-d] pyrimidin-7-one was prepared from the title compound of Preparation 12 and Preparation 4 6 according to the procedure of Preparation 15B as a white solid (4 %). 5 (CDC 1 3): 0.98 (3H, t), 1 · 1 2 (3 Η, t), 1 · 8 3 (2 Η, m), 1 · 9 7 (2 Η, m), 2 · 9 2 (2 Η, t), 3.80 (3H, s), 4 · 1 6 (2 Η, t), 5 · 9 6 (2 Η, s), 7 · 0 〇 (1 Η, d), 7 · 1 0 (3 Η, m), 7 · 4 1 (1 Η, m), 8 · 〇1 (1 Η, d), 8 · 4 8 (1 Η, d), 11. 8 (1H, s ) ° This paper size applies to Chinese National Standard (CNS) A4 specification (210X297 mm) ~-224-(Please read the precautions on the back before filling this page) —0.

、1T t 524805 經濟部中央標準局員工消費合作社印製 A7 五、發明説明（222) LRMS:m/z 434(M+1)+。 製備例4 8 2 — (3 —甲氧吡啶一 2 —基）甲基一5 —（2 —正 丙氧苯基）一 3 -正丙基—2，6 —二氫一 7H -吡唑並 〔4，3 — d〕嘧啶一 7 —酮 由製備例1 2及製備例4 6之標題化合物依製備例 15B之步驟製得，呈白色固體（78%)。 5(CDCl3):〇.98(3H，t)， 1 ·〇 6 ( 3 Η，t )， 1 · 7 8 ( 2 Η，m )， 1 · 9 5 ( 2 Η，m )， 2 · 9 7 ( 2 Η，t ·)， 3 · 8 3 ( 3 Η，s )， 4 · 1 2 ( 2 Η，t )， 5 · 6 6 ( 2 Η，s )， 6 · 9 9 ( 1 Η，d )， 7 · 0 6 ( 1 Η，m )， 7 · 1 8 ( 2 Η，m )， 7 · 3 9 ( 1 Η，m )， 8 ·〇 6 ( 1 Η，d )， 8 · 3 8 ( 1 Η，d )， 1〇·7〇（1ϋ，δ)° L R Μ S ： m / z 434(M+1)+。 本纸張尺度適用中國國家標準（CNS ) A4規格（210X297公ϋ~-225 - (請先閱讀背面之注意事項再填寫本頁) 、1Τ i# 4 524805 A7 B7 五、發明説明（223) 經濟部中央標準局員工消費合作社印繫 製備例4 9 2 一 ( 6 — 三 甲 基 乙 醯 基 胺 基 吡 D定一 2 一基 ) 甲某— 5 — ( 2 — 正 丙 氧 苯 基 ) — 3 — 正 丙 基一 2 ，6 — 二氫― 7 Η — 吡 唑 並 [ 4 3 — d ] 嘧 啶 — 7 - 酮 由 製 備 例 1 2 之 標 題 化 合 物 及 2 一溴 甲 基一 6 一三甲 基 乙 醯 基 胺 基 吡 D定 ( Chem. Lett • ? 1 995， 61 )依ί 製 備例 1 5 Β 之 步 驟 製 得 呈 白 色 固 體 ( 7 8 % ) 〇 δ ( C D C 1 3 ) :〇 9 ( 9 ( 3 Η ，t ) 5 1 • 1 2 ( 3 Η t ) 1 • 3 6 ( 9 Η ， S ) 1 • 7 9 ( 2 Η m ) 2 • 〇 〇 ( 2 Η ? m ) 2 參 9 5 ( 2 Η t ) 4 • 1 8 ( 2 Η ， t ) 5 • 5 5 ( 2 Η s ) 6 • 7 〇 ( 1 Η d ) 7 • 〇 4 ( 1 Η y d ) 7 • 1 2 ( 1 Η 5 m ) 5 7 • 4 3 ( 1 Η m ) 7 • 6 1 ( 1 Η 5 m ) 5 7 • 9 6 ( 1 Η J s ) 8 • 1 6 ( 1 Η d ) ， 8 4 〇 ( 1 Η d ) 5 本紙張尺度適用中國國家標準（CNS ) A4規格（210X 297公釐）-226 - (讀先閱讀背面之注意事項再填寫本頁) 524805 Α7 Β7 五、發明説明（224) l〇.90(lH，s)° LRMS:m/z 5〇3(M+1)+。 製備例5〇 1 一（6 —三甲基乙醯基胺基吡啶一 2 —基）甲基一 5 -（2 —正丙氧苯基）—3 -正丙基—1 ，6 -二氫— 7H —吡唑並〔4，3 — d〕嘧啶一 7 —酮 由製備例1 2之標題化合物及2 —溴甲基一 6 —三甲 基乙醯基胺基吡啶（Chem. Lett·，1 995，61 )依製備例 15B之步驟製得，呈白色固體（12%)。 5(CDCl3):l.〇〇（3H，t)， 1 · 1 6 ( 3 Η，t )， 1 · 3 2 ( 9 Η，s )， 1 · 9 Ο ( 2 Η，m )， 2 .〇〇（2 Η ， m )， 2 · 9 8 ( 2 Η，t )， 4 · 1 7 ( 2 Η，t )， 經濟部中央標準局員工消費合作社印製 (讀先閱讀背面之注意事項再填寫本頁) 5 · 8 〇（2 Η，s )， 6 · 7 〇（1 Η，d )， 7 ·〇 5 ( 1 Η，d )， 7 · 1 4 ( 1 Η，m )， 7 · 4 6 ( 1 Η，m )， 7 · 5 9 ( 1 Η，m )， 7 · 9 9 ( 1 Η ，s )， 本纸張尺度適用中國國家標準（CNS ) A4規格（210X 297公釐）_ 227 524805 A7 經濟部中央標準局員工消費合作社印製 五、發明説明（225) 8 · 1 2 ( 1 Η，s )， 8 · 5 2 ( 1 Η，d )， 11.22(lH，s)° LRMS:m/z 5〇3(M+1)+。 製備例5 1 1一（1 一甲基咪唑一2 —基）甲基一5 — (2 —正 丙氧苯基）一 3 —正丙基一 1 ，6 —二氫—7H —吡唑並 〔4，3 — d〕嘧啶—7 —酮 由製備例1 2之標題化合物及2 -氯甲基一 1 一甲基 咪唑鹽酸（J. Chem. Soc·，1 957，3305 )之自由鹼依製備 例15B之步驟製得，呈白色固體（2 1%)。。 5(CDCl3):l.〇〇（3H，t)， 1 · 1 8 ( 3 Η，t )， 1 · 8 6 ( 2 Η，m )， 2 . 0 2 ( 2 Η ^ m )， 2 · 9 2 ( 2 Η，t )， 3 · 7 〇（3 Η，s )， 4 · 1 9 ( 2 Η，t )， 6 · Ο 4 ( 2 Η，s )， 6 · 8 2 ( 1 Η，s )， 7 · 0 5 ( 1 Η，d )， 7 · 1 6 ( 1 Η，m )， 7 · 4 6 ( 1 Η，m )， 本纸張尺度適用中國國家標準（CNS ) Α4規格（21 ΟΧ 297公釐）-228 - (讀先閲讀背面之注意事項再填寫本頁) 衣· 、1Τ1T t 524805 Printed by the Consumer Cooperatives of the Central Standards Bureau of the Ministry of Economic Affairs A7 V. Invention Description (222) LRMS: m / z 434 (M + 1) +. Production Example 4 8 2 — (3-methoxypyridine-2-yl) methyl-5— (2-n-propoxyphenyl) -3—n-propyl-2,6-dihydro-7H-pyrazolo [4,3-d] Pyrimidine-7-one was prepared from the title compound of Preparation 12 and Preparation 6 by the procedure of Preparation 15B as a white solid (78%). 5 (CDCl3): 0.98 (3H, t), 1.06 (3 Η, t), 1 · 7 8 (2 Η, m), 1 · 9 5 (2 ，, m), 2 · 9 7 (2 Η, t ·), 3 · 8 3 (3 Η, s), 4 · 1 2 (2 Η, t), 5 · 6 6 (2 Η, s), 6 · 9 9 (1 Η, d), 7 · 0 6 (1 Η, m), 7 · 1 8 (2 Η, m), 7 · 3 9 (1 Η, m), 8 · 〇6 (1 Η, d), 8 · 3 8 (1 Η, d), 10.7 (0 ϋ, δ) ° LR M S: m / z 434 (M + 1) +. This paper size applies to China National Standard (CNS) A4 specifications (210X297 cm ~ -225-(Please read the precautions on the back before filling this page), 1Τ i # 4 524805 A7 B7 V. Description of the invention (223) Economy Ministry of Standards Bureau, Department of Consumer Cooperatives, Printing Department, Preparation Example 4 9 2 1 (6-Trimethylethylamidopyridine D, 1-2-1) A-5-(2-n-propoxyphenyl)-3 —N-propyl-2,6-dihydro-7 pyrene-pyrazolo [4 3 — d] pyrimidin-7-one was prepared from the title compound of Preparation 1 2 and 2 monobromomethyl-6 trimethylethyl Pyridylaminopyridine (Chem. Lett •? 1 995, 61) was prepared as a white solid (78%) according to the procedure of Preparation Example 15B, δ (CDC 1 3): 〇9 (9 ( 3 Η, t) 5 1 • 1 2 (3 Η t) 1 • 3 6 (9 Η, S) 1 • 7 9 (2 Η m) 2 • 〇〇 (2 Η? M) 2 See 9 5 (2 Η t) 4 • 1 8 (2 Η, t) 5 • 5 5 (2 Η s) 6 • 7 〇 (1 Η d) 7 • 〇4 (1 Η yd) 7 • 1 2 (1 Η 5 m) 5 7 • 4 3 (1 Η m) 7 • 6 1 (1 Η 5 m) 5 7 • 9 6 (1 Η J s) 8 • 1 6 (1 Η d), 8 4 〇 (1 Η d) 5 This paper size applies Chinese National Standard (CNS) A4 specification (210X 297 mm) -226-( Read the notes on the back before filling in this page) 524805 Α7 Β7 V. Description of the invention (224) l90.90 (lH, s) ° LRMS: m / z 503 (M + 1) +. Preparation Example 501 mono (6-trimethylethylamidoaminopyridine-2-yl) methyl 5- (2-n-propoxyphenyl) -3-n-propyl-1,6-dihydro — 7H —pyrazolo [4,3 — d] pyrimidin-7-one was prepared from the title compound of Preparation Example 12 and 2-bromomethyl-6-trimethylacetamidopyridine (Chem. Lett ·, 1 995, 61) was prepared according to the procedure of Preparation 15B, and it was a white solid (12%). 5 (CDCl3): 1.0 (3H, t), 1 · 16 (3 Η, t), 1 · 3 2 (9 Η, s), 1 · 9 〇 (2 Η, m), 2. 〇〇 (2 Η, m), 2 · 98 (2 Η, t), 4 · 17 (2 Η, t), printed by the Consumer Cooperatives of the Central Standards Bureau of the Ministry of Economic Affairs (read the precautions on the back before reading) Fill out this page) 5 · 8 〇 (2 Η, s), 6 · 7 〇 (1 Η, d), 7 · 〇5 (1 Η, d), 7 · 1 4 (1 1, m), 7 · 4 6 (1 Η, m), 7 · 5 9 (1 Η, m), 7 · 9 9 (1 Η, s), this paper size applies Chinese National Standard (CNS) A4 (210X 297 mm) _ 227 524805 A7 Printed by the Consumer Cooperatives of the Central Bureau of Standards of the Ministry of Economic Affairs 5. Description of the invention (225) 8 · 1 2 (1 Η, s), 8 · 5 2 (1 Η, d), 11.22 (lH, s) ° LRMS: m / z 503 (M + 1) +. Preparation Example 5 1 1- (1-methylimidazol-2-yl) methyl 5- 5- (2-n-propoxyphenyl) -3-n-propyl-1,6-dihydro-7H-pyrazolo [4,3 — d] Pyrimidin-7-one was prepared from the title compound of Preparation 12 and 2-chloromethyl-1,1-methylimidazole hydrochloride (J. Chem. Soc ·, 1 957, 3305) as the free base. Prepared by the procedure of Preparation Example 15B as a white solid (21%). . 5 (CDCl3): 1.0 (3H, t), 1 · 1 8 (3 Η, t), 1 · 8 6 (2 Η, m), 2.0 2 (2 Η ^ m), 2 · 9 2 (2 Η, t), 3 · 7〇 (3 Η, s), 4 · 1 9 (2 Η, t), 6 · Ο 4 (2 Η, s), 6 · 8 2 (1 Η, s), 7 · 0 5 (1 Η, d), 7 · 16 (1 Η, m), 7 · 4 6 (1 Η, m), this paper size applies to China National Standard (CNS) Α4 specifications ( 21 ΟΧ 297 mm) -228-(Read the precautions on the back before filling in this page) Clothing, 1T

524805 A7 B7 五、發明説明（226) 8 · 5 〇（1 Η，d )， 11.26(lH，s)。 L R M S ： m / z 407 (M+1)+。 製備例5 2 2 —（1—甲基咪唑—2 —基）甲基一5 —（2 —正 丙氧苯基）一 3 —正丙基一 2，6 —二氫一 7H —吡唑並 〔4，3 — d〕嘧啶—7 -酮 由製備例1 2之標題化合物及2 —氯甲基一 1 一甲基 咪唑鹽酸（J. Chem. Soc·，1957，3305 )之自由鹼依製備 例15B之步驟製得，呈白色固體（18%)。。 5 ( C D C 1 3 ) :0.98(3H，t)， 1 · 1 4 ( 3 Η，t )， 1 · 7 5 ( 2 Η，m )， 1.99(2H，m)， 本纸張尺度適用中國國家標準（CNS ) A4規格（21〇X 297公釐）-229 - (讀先閱讀背面之注意事項再填寫本頁)524805 A7 B7 V. Description of the invention (226) 8.5 (1 Η, d), 11.26 (1H, s). L R M S: m / z 407 (M + 1) +. Preparation Example 5 2 2 — (1-methylimidazol-2-yl) methyl—5— (2-n-propoxyphenyl) —3—n-propyl—2,6—dihydro—7H —pyrazolo [4,3 — d] Pyrimidin-7-one was prepared from the title compound of Preparation Example 12 and 2-chloromethyl-1,1-methylimidazole hydrochloride (J. Chem. Soc ·, 1957, 3305) as the free base. Example 15B was prepared as a white solid (18%). . 5 (CDC 1 3): 0.98 (3H, t), 1 · 1 4 (3 Η, t), 1 · 7 5 (2 Η, m), 1.99 (2H, m), this paper size is applicable to China Standard (CNS) A4 Specification (21〇X 297mm) -229-(Read the precautions on the back before filling in this page)

tstssdmmd Ji J1 J1 T_1 THX THi Tu -LF- TrA T_i Tr_ _L1 TUI Tr_ _L1 ΤΓ 23221—- -—- -—111—_ xfv /(V rv r\ /l\ /IV /l\ /(V 268742348 171680143 334567778 經濟部中央標準局員工消費合作社印製 \)y \ly 524805 經濟部中央標準局員工消費合作社印製 A7 B7 五、發明説明（227) l〇.87(lH，s)。 LRMS:m/z 40 7 (M+1)+。 製備例5 3 1 一（3 ，5 —二甲基異哼唑一4 一基）甲基一 5 — (2 -正丙氧苯基）一 3 -正丙基—1，6 -二氫一 7H 一吡唑並〔4，3 — d〕嘧啶—7 -酮 由製備例12之標題化合物及4 一氯甲基一 3，5 -二甲基異nfD坐依製備例1 5 D之步驟製得，呈白色固體（ 4 4%)。 元素分析實測値：C，6 5 · 4 0 ; Η，6 · 4 7 ; N， 16 · 53。C23H27N5〇3計算値 C，65 . 54 ; Η，6·49 ;N，16.62%。 5(CDCl3):l.〇2(3H，t)， 1 · 1 7 ( 3 Η，t ) ’ 1 · 8 6 ( 2 Η，m )， 2 ·〇 2 ( 2 Η，m )， 2 · 3 5 ( 3 Η，s )， 2 · 5 2 ( 3 Η，s )， 2 · 9 2 ( 2 Η，t )， 4 · 1 9 ( 2 Η，t )， 5 · 5 6 ( 2 Η，s )， 7 ·〇 5 ( 1 Η，d )， 7 · 1 6 ( 1 Η ，m )， 本紙張尺度適用中國國家標準（CNS ) A4規格（210X297公釐）-230 - (請先閲讀背面之注意事項再填寫本頁)tstssdmmd Ji J1 J1 T_1 THX THi Tu -LF- TrA T_i Tr_ _L1 TUI Tr_ _L1 ΤΓ 23221 — — — — — — — 111 —_ xfv / (V rv r \ / l \ / IV / l \ / (V 268742348 171680143 334567778 Printed by the Consumer Cooperatives of the Central Standards Bureau of the Ministry of Economic Affairs \) y \ ly 524805 Printed by the Consumer Cooperatives of the Central Standards Bureau of the Ministry of Economic Affairs A7 B7 V. Description of the invention (227) l0.87 (lH, s). z 40 7 (M + 1) +. Preparation Example 5 3 1 Mono (3,5-dimethylisohumidazole-4 mono) methyl 5- (2-n-propoxyphenyl) -3-n Propyl-1,6-dihydro-7H-pyrazolo [4,3-d] pyrimidin-7-one was prepared from the title compound of Preparation 12 and 4 monochloromethyl-3,5-dimethylisonfD Obtained according to the procedure of Preparation 1D D, as a white solid (44%). Elemental analysis: 値: C, 6 5 · 4 0; Η, 6 · 4 7; N, 16 · 53. C23H27N503 Calculate 値 C, 65.54; Η, 6.49; N, 16.62%. 5 (CDCl3): 1.02 (3H, t), 1 · 1 7 (3 Η, t) '1 · 8 6 ( 2 Η, m), 2 · 〇2 (2 Η, m), 2 · 3 5 (3 Η, s), 2 · 5 2 (3 Η, s), 2 · 9 2 (2 Η, t), 4 · 1 9 (2 Η, t), 5 · 5 6 (2 Η, s), 7 · 〇5 (1 Η, d), 7 · 1 6 (1 Η, m), this paper size applies Chinese National Standard (CNS ) A4 size (210X297mm) -230-(Please read the precautions on the back before filling this page)

、1T, 1T

524805 A7 B7五、發明説明（228) 7 · 4 6 ( 1 Η，m )， 8 · 5 〇（1 Η，d )， 1 1 · 1 6 ( 1 Η，s )。 LRMS:m/z 422 (M+1)+。 製備例5 4 5— (2 —乙氧苯基）一3 —甲基一1 一（3 ，5 — 二甲基異噚唑一4 一基）甲基一 1 ，6 —二氫一7H —吼 唑並〔4，3 - d〕嘧啶—7 -酮 由製備例3 9之標題化合物及4 一氯甲基一 3，5 — 二甲基異二唑依製備例1 5 A之步驟製得，呈白色固體（ 7 2%)。元素分析實測値：C，6 3 · 1 9 ; Η，5 · 5 5 ; N， 18 · 3 0 。C2〇H21N5〇3計算値 C ，63 . 31 ; Η，5·58;Ν，18·46%。 經濟部中央標準局員工消費合作社印製 3 HHHHHHHH .—- oo no 〇〇 cxi 1± lx ti~~_ ^' /(V '\ /X /^' /l\ /IV /(V D42246561 C35350145 xfv ········ 522457778 ， s \)/ X s 2524805 A7 B7 V. Description of the invention (228) 7 · 4 6 (1 Η, m), 8 · 5 〇 (1 Η, d), 1 1 · 1 6 (1 Η, s). LRMS: m / z 422 (M + 1) +. Preparation Example 5 4 5- (2-ethoxyphenyl) -3-methyl-1 1- (3,5-dimethylisoxazole-4-yl) methyl-1,6-dihydro-7H- Amidazo [4,3-d] pyrimidin-7-one was prepared from the title compound of Preparation Example 9 and 4 monochloromethyl-3,5-dimethylisodiazole according to the procedure of Preparation Example 5 A As a white solid (7.2%). Elemental analysis: 値: C, 6 3 · 19; Η, 5 · 5 5; N, 18 · 30. C20H21N50 was calculated as 値 C, 63.31; Η, 5.58; N, 18.46%. Printed by the Consumer Cooperatives of the Central Standards Bureau of the Ministry of Economic Affairs 3 HHHHHHHH .—- oo no 〇〇cxi 1 ± lx ti ~~ _ ^ '/ (V' \ / X / ^ '/ l \ / IV / (V D42246561 C35350145 xfv ······· 522457778 ， s \) / X s 2

Q N)/ \)y \)y \)y N)y s d m m d 4 6 Η 3 (請先閲讀背面之注意事項再填寫本頁)Q N) / \) y \) y \) y N) y s d m m d 4 6 Η 3 (Please read the notes on the back before filling this page)

本紙張尺度適用中國國家標準（CNS ) A4規格（210X 297公釐）-231 - 524805 經濟部中央標隼局員工消費合作社印製 A7 B7五、發明説明（229) 11.18(lH，s)。 LRMS:m/z 38〇（M+1)+。 製備例5 5 2— (3 ，5 — 一甲基異啤哩一4 一基）甲基一5 — (2 -正丙氧苯基）一 3 -正丙基一 2，6 -二氫一 7H 一吡唑並〔4，3 - d〕嘧啶一 7 -酮 由製備例之標題化合物及4 一氯甲基一 3，5-二甲基異噚唑依製備例1 5 D之步驟製得，呈白色固體（ 16%)。 元素分析實測値：C，6 4 · 8 8 ; Η，6 · 4 1 ; N， 16 · 33。C23H27N5〇3 計算値 C，65 · 54 ； Η，6·49;Ν，16.62%。 5(CDCl3):l.〇〇（3H，t)， 1 · 1 4 ( 3 Η，t )， 1 . 7 8 ( 2 Η，m )， 1 · 9 8 ( 2 Η，m )， 2 · 1 7 ( 3 Η，s )， 2 · 3 6 ( 3 Η，s )， 2 · 9 〇（2 Η，t )， 4 · 1 8 ( 2 Η，t )， 5 · 2 8 ( 2 Η，s )， 7 ·〇 2 ( 1 Η，d )， 7 · 1 2 ( 1 Η，m )， 本紙張尺度適用中國國家標準（CNS ) A4規格（21 ox297公釐）_ 232 _ (讀先閲讀背面之注意事項再填寫本頁) 衣.This paper size applies to Chinese National Standard (CNS) A4 specifications (210X 297 mm) -231-524805 Printed by the Consumer Cooperatives of the Central Bureau of Standards of the Ministry of Economic Affairs A7 B7 V. Invention Description (229) 11.18 (lH, s). LRMS: m / z 38 ° (M + 1) +. Preparation Example 5 5 2— (3,5-—Isomethylisopropyl-1-methyl) —methyl—5- (2-n-propoxyphenyl) —3—n-propyl—2,6-dihydro— 7H-pyrazolo [4,3-d] pyrimidin-7-one was prepared from the title compound of Preparation Example and 4-chlorochloro-3,5-dimethylisoxazolyl according to the procedure of Preparation Example 5 D As a white solid (16%). Elemental analysis: 値: C, 6 4 · 8 8; Η, 6 · 4 1; N, 16 · 33. C23H27N503 Calculates 値 C, 65 · 54; Η, 6.49; N, 16.62%. 5 (CDCl3): 1.0 (3H, t), 1 · 1 4 (3 t, t), 1. 7 (2 m, m), 1 · 9 8 (2 Η, m), 2 · 1 7 (3 Η, s), 2 · 3 6 (3 Η, s), 2 · 9 〇 (2 Η, t), 4 · 1 8 (2 Η, t), 5 · 2 8 (2 Η, s), 7 · 〇2 (1 Η, d), 7 · 12 (1 Η, m), this paper size applies Chinese National Standard (CNS) A4 specification (21 ox297 mm) _ 232 _ (read first read (Notes on the back then fill out this page) clothing.

、1T, 1T

524805 經濟部中央標準局員工消費合作社印製 A7 B7 五、發明説明（230) 7 · 4 3 ( 1 Η，m )， 8 · 3 8 ( 1 Η，d )， 1〇·9〇（1Η，δ)。 LRMS:m/z 422 (M+1)+。 製備例5 6 1— (2 —甲基嚷卩坐一 4 —基）甲基一5 — (2 —正 丙氧苯基）一 3 -正丙基一 1，6 -二氫一 7H -吡唑並 〔4，3 — d〕嘧啶—7 —酮 由製備例12之標題化合物及4一氯甲基一2—甲基 噻唑鹽酸鹽之自由鹼依製備例1 5 D之步驟製得，呈白色 粉末（3〇％ )。 元素分析實測値：C，6 1 · 3 2 ; Η，5 · 8 6 ; N， 16 ·〇8 。 C22H25N5〇2，S ;〇· 4〇H2〇計算値 C，61.35;H，6.〇4;N，16.26%。 (5(CDCl3)：l.〇3(3H^t)^ 1 · 1 8 ( 3 Η，t )， 1 · 9 〇（2 Η，m )， 2 ·〇 1 ( 2 Η，m )， 2 · 6 7 ( 3 Η，s )， 2 . 9 8 ( 2 Η，t )， 4 · 2 〇（2 Η，t )， 5 · 9 0 ( 2 Η，s )， 6 · 8 8 ( 1 Η ， s )， 本紙張尺度適用中國國家標準（CNS ) Α4規格（210X297公釐）_之33 (請先閱讀背面之注意事項再填寫本頁 訂524805 Printed by the Consumer Cooperative of the Central Standards Bureau of the Ministry of Economic Affairs A7 B7 V. Description of the invention (230) 7 · 4 3 (1 Η, m), 8 · 3 8 (1 Η, d), 1 · 9〇 (1Η, δ). LRMS: m / z 422 (M + 1) +. Preparation Example 5 6 1- (2-methylfluorenyl-4-yl) methyl-5- (2-n-propoxyphenyl) -3-n-propyl-1,6-dihydro-7H-pyridine Zolo [4,3-d] pyrimidin-7-one was prepared from the title compound of Preparation 12 and the free base of 4-chloromethyl-2-methylthiazole hydrochloride according to the procedure of Preparation 15D. White powder (30%). Elemental analysis: 値: C, 6 1 · 3 2; Η, 5 · 8 6; N, 16 · 08. C22H25N502, S; 0.40H2O calculated C, 61.35; H, 6.04; N, 16.26%. (5 (CDCl3): 1.03 (3H ^ t) ^ 1 · 1 8 (3 Η, t), 1 · 9 〇 (2 Η, m), 2 · 〇1 (2 Η, m), 2 · 6 7 (3 Η, s), 2. 9 8 (2 Η, t), 4 · 2 〇 (2 Η, t), 5 · 9 0 (2 Η, s), 6 · 8 8 (1 Η , S), this paper size applies to Chinese National Standard (CNS) Α4 specification (210X297 mm) _ of 33 (Please read the precautions on the back before filling in this page to order

524805 A7 B7五、發明説明（231) 7.05(lH，d)， 7 · 1 6 ( 1 Η，m )， 7 · 4 6 ( 1 Η，m )， 8 · 5 2 ( 1 Η，d )， 1 1 · 2 〇（1 Η ， s )。 LRMS:m/z 424 (M+1)+。 製備例5 7 5— (2 —乙氧苯基）一 3 —甲基一 2 — (2 —甲基 噻唑—4一基）甲基一 2，6 —二氫一 7H —吡唑並〔4 ，3 — d〕喃D定一 7 —酮 由製備例3 9之標題化合物及4 一氯甲基一 2 —甲基 噻d坐鹽酸鹽之自由鹼依製備例1 5 B之步驟製得，呈白色 固體（2 2 % )。 元素分析實測値·· C，5 9 · 4 7 ; Η，4 · 9 5 ; N， (請先閲讀背面之注意事項再填寫本頁)524805 A7 B7 V. Description of the invention (231) 7.05 (lH, d), 7 · 16 (1 Η, m), 7 · 4 6 (1 Η, m), 8 · 5 2 (1 Η, d), 1 1 · 2 0 (1 Η, s). LRMS: m / z 424 (M + 1) +. Production Example 5 7 5— (2-Ethoxyphenyl) —3-methyl—2— (2-methylthiazole-4—yl) methyl—2,6-dihydro—7H—pyrazolo [4 , 3 — d] N-D-A-7-one was prepared from the title compound of Preparation Example 3 and 9 and the free base of 4-chlorochloromethyl-2-methylthiazine hydrochloride according to the procedure of Preparation Example 5 B As a white solid (22%). Elemental analysis measured 値 ·· C, 5 9 · 4 7; Η, 4 · 9 5; N, (Please read the precautions on the back before filling this page)

、1T, 1T

c o o IX 8 IX Η S 2 〇 5 Ν 經濟部中央標準局員工消費合作社印掣 2 3 Η Η Η Η Η H 0 1 3 3 2 2 11 . c /IV /IV /(X /l\ /l\ rv 5D598004 ， c 6 6 2 6 9 〇 Η/IV · ; 5 2 2 4 5 6 7 Ν s s Q s s d 8 8 5 6 3 3 計^Η C 値 算 3 8 9 5coo IX 8 IX Η S 2 〇5 Ν Employees' cooperatives of the Central Standards Bureau of the Ministry of Economic Affairs 2 3 Η Η Η Η Η H 0 1 3 3 2 2 11. c / IV / IV / (X / l \ / l \ rv 5D598004, c 6 6 2 6 9 〇Η / IV ·; 5 2 2 4 5 6 7 Ν ss Q ssd 8 8 5 6 3 3 Calculate ^ Η C Calculate 3 8 9 5

本紙張尺度適用中國國家標準（CNS ) Α4規格（210X297公釐）-234 - 經濟部中央標準局員工消費合作社印製 524805 A7 B7 五、發明説明（232) 7 · 1 3 ( 1 Η，m )， 7 · 4 4 ( 1 Η，m )， 8 · 4 2 ( 1 Η，d )， 1 〇· 8 5 ( 1 Η ， s ) ° L R M S ： m / z 382 (M+1)+。 製備例5 8 2 —（2 —甲基噻唑一4 —基）甲基一 5 —（2 —正 丙氧苯基）一 3 —正丙基一 2，6 — —*氨—7 Η —吼哗並 〔4，3 — d〕喃 d定—7 —酮 由製備例12之標題化合物及4一氯甲基一2—甲基 噻唑鹽酸鹽之自由鹼依製備例1 5 D之步驟製得，呈白色 粉末（1 0 % )。 元素分析實測値：C，6 1 · 9 0 ; Η，6 · 0 4 ; N， 15 · 95 。C22H25N5〇2S ；〇.20H2〇計算値 C，61.86;H，5.99;N，16.40%。 (5(CDCl3):l. 〇〇(3H，t)， 1 · 1 4 ( 3 Η，t )， 1 · 8 〇（2 Η，m )， 2 ·〇 0 ( 2 Η，m )， 2 · 7 0 ( 3 Η，s )， 3 ·〇 4 ( 2 Η，t )， 4 · 1 8 ( 2 Η，t )， 5 · 6 3 ( 2 Η，s )， 本紙張尺度適用中國國家標準（CNS ) Α4規格（21 ΟΧ 297公釐）-235 - (請先閱讀背面之注意事項再填寫本頁)This paper size applies to Chinese National Standard (CNS) A4 (210X297 mm) -234-Printed by the Consumer Cooperatives of the Central Standards Bureau of the Ministry of Economic Affairs 524805 A7 B7 V. Description of the Invention (232) 7 · 1 3 (1 Η, m) , 7 · 4 4 (1 Η, m), 8 · 4 2 (1 Η, d), 1 · 8 5 (1 Η, s) ° LRMS: m / z 382 (M + 1) +. Preparation Example 5 8 2 — (2-methylthiazole—4-yl) methyl—5— (2-n-propoxyphenyl) —3—n-propyl—2,6 — — * Ammonia—7 Η —Roar [4,3 — d] anodin-7 —one was prepared from the title compound of Preparation 12 and the free base of 4-chlorochloro-2-methylthiazole hydrochloride according to the procedure of Preparation 5 D It was obtained as a white powder (10%). Elemental analysis: 値: C, 6 1 · 9 0; Η, 6 · 0 4; N, 15 · 95. C22H25N502S; 0.20H2O calculated C, 61.86; H, 5.99; N, 16.40%. (5 (CDCl3): 1. 〇〇 (3H, t), 1.14 (3 Η, t), 1.8 〇 (2 Η, m), 2. 〇0 (2 m, m), 2 · 7 0 (3 Η, s), 3 · 〇 4 (2 Η, t), 4 · 1 8 (2 Η, t), 5 · 6 3 (2 Η, s), this paper size applies Chinese national standards (CNS) Α4 specification (21 〇Χ 297mm) -235-(Please read the precautions on the back before filling this page)

524805 A7 B7五、發明説明（233) 6 . 8 6 ( 1 Η，s )， 7 ·〇 5 ( 1 Η，d )， 7 · 1 4 ( 1 Η，m )， 7 · 4 4 ( 1 Η，m )， 8 · 4 0 ( 1 Η，d )， l〇.85(lH，s)° L R M S ： m / z 424 (M+1)+。 製備例5 9 1— (1—甲基一 1 ，2，4 —三唑一5 —基）甲基 一 5 -（2 -正丙氧苯基）—3 —正丙基一 1，6 —二氫 —7 Η —吡唑並〔4，3 - d〕嘧啶一 7 —酮 由製備例1 2之標題化合物及5 —氯甲基一 1 一甲基 —1，2，4 —三 D坐鹽酸鹽（J. Antibiotics，1993，46_, 1 8 66 )之自由鹼依製備例1 5 B之步驟製得，呈白色固體 (31%)。 經濟部中央標隼局員工消費合作社印製 2 2 3 4 5 \)/ \)/ \)/ \)y \)x \ly v丄 tmmt s t s \)/ THX THX THX tha thx thx thx 3 TUI THX Thx ΤΓ* TUI Thx Thx 13222322 G rv /fvv /' /f\ /^' rv /IV D8624807 C1809929 Η 3 /(\ 〇 ο (請先閲讀背面之注意事項再填寫本頁)524805 A7 B7 V. Description of the invention (233) 6. 8 6 (1 Η, s), 7 · 05 (1 Η, d), 7 · 1 4 (1 Η, m), 7 · 4 4 (1 Η , M), 8.40 (1 Η, d), 10.85 (lH, s) ° LRMS: m / z 424 (M + 1) +. Preparation Example 5 9 1- (1-methyl-1,2,4-triazole-5-yl) methyl-5- (2-n-propoxyphenyl) -3-n-propyl-1,6- Dihydro-7 pyrene-pyrazolo [4,3-d] pyrimidin-7-one was prepared from the title compound of Preparation Example 12 and 5-chloromethyl-1 1-methyl-1, 2, 4-tris The free base of the hydrochloride (J. Antibiotics, 1993, 46_, 1 8 66) was prepared according to the procedure of Preparation Example 15B, as a white solid (31%). Printed by the Consumer Cooperatives of the Central Bureau of Standards, Ministry of Economic Affairs 2 2 3 4 5 \) / \) / \) / \) y \) x \ ly v 丄 tmmt sts \) / THX THX THX tha thx thx thx 3 TUI THX Thx ΤΓ * TUI Thx Thx 13222322 G rv / fvv / '/ f \ / ^' rv / IV D8624807 C1809929 Η 3 / (\ 〇ο (Please read the precautions on the back before filling this page)

本纸張尺度適用中國國家標準（CNS ) A4規格（210X 297公釐）-236 - 524805 A7 B7 五、發明説明（234) 經濟部中央標隼局員工消費合作社印製 7 • 〇 6 ( 1 Η 9 d ) ? 7 • 1 6 ( 1 Η 5 m ) 5 7 • 4 6 ( 1 Η 1 m ) 5 7 • 8 3 ( 1 Η s ) J 8 • 5 〇 ( 1 Η d ) 5 1 1 • 2 7 ( 1 Η s )° L R Μ S m / ζ 4 〇8 ( Μ + 1 )+ ° 製 備 例 6 〇 2 — ( 1 — 甲 基 — 1， 2 4 - 三口坐— 5 一基 )甲 基 — 5 — ( 2 — 正 丙 氧 苯 基） — 3 -正 丙基一 2 ，6 -二 氫 — 7 Η — 吡 唑 並 [ 4 5 3 - d ] 嘧啶 -7 — 酮 由 製 備 例 1 2 之 標 題化 合 物 及5 一氯甲 基 -1 -甲 基 — 1 2 y 4 — 三 唑 鹽 酸鹽 ( J. Antibiotics 1 993, 16.， 1866 ) 之 白 由 鹼 依 製 備 例1 5 Β 之步 驟製得 j 呈te —c- J\\\ 色泡 沬 狀 ( 2 5 % ) ο 5 ( C D C 1 3 ； ) 1 •〇 〇 ( 3 Η ，t ) 5 1 • 1 4 ( 3 Η ? t ) 1 • 8 〇 ( 2 Η 5 m ) ， 1 • 9 9 ( 2 Η 5 m ) j 3 • 〇 9 ( 2 Η > t ) j 4 • 〇 〇 ( 3 Η s ) j 4 • 1 8 ( 2 Η t ) 5 5 7 2 ( 2 Η 5 s ) 5 本紙張尺度適用中國國家標準（CNS ) Α4規格（210X297公釐）-237 - (讀先閱讀背面之注意事項再填寫本頁)This paper size applies to Chinese National Standard (CNS) A4 (210X 297 mm) -236-524805 A7 B7 V. Description of the invention (234) Printed by the Consumers' Cooperative of the Central Bureau of Standards, Ministry of Economic Affairs 7 • 〇6 (1 Η 9 d)? 7 • 1 6 (1 Η 5 m) 5 7 • 4 6 (1 Η 1 m) 5 7 • 8 3 (1 Η s) J 8 • 5 〇 (1 Η d) 5 1 1 • 2 7 (1 Η s) ° LR Μ S m / ζ 4 〇 8 (Μ + 1) + ° Preparation Example 6 〇 2 — (1 —methyl — 1, 2 4-three-mouthed — 5 -yl) methyl — 5 — (2 —n-propoxyphenyl) — 3 -n-propyl-2,6-dihydro — 7 hydrazone — pyrazolo [4 5 3-d] pyrimidine-7 —-one by the title of Preparation Example 1 2 Compound and 5-monochloromethyl-1 -methyl — 1 2 y 4 —triazole hydrochloride (J. Antibiotics 1 993, 16., 1866) were prepared from a base in accordance with the procedure of Preparation Example 15 B It is te —c- J \\\ color bubble 沬 shape (2 5%) ο 5 (CDC 1 3;) 1 • 〇〇 (3 Η, t) 5 1 1 4 (3 Η? T) 1 • 8 〇 (2 Η 5 m), 1 • 9 9 (2 Η 5 m) j 3 • 〇9 (2 Η > t) j 4 • 〇〇 (3 Η s ) j 4 • 1 8 (2 Η t) 5 5 7 2 (2 Η 5 s) 5 This paper size applies to China National Standard (CNS) Α4 size (210X297 mm) -237-(Read the precautions on the back before reading (Fill in this page again)

、1T, 1T

5248〇5 經濟部中央標準局員工消費合作社印製 A7 B7 五、發明説明（235) 7 ·〇 4 ( 1 Η，d )， 7 · 1 4 ( 1 Η，m )， 7-45(lH，m)， 7 · 8 4 ( 1 H，s )， 8 · 3 9 ( 1 H，d )， 。 L R M S ： m / z 4〇8(M+1)+。 製備例6 1 1— (2 —甲氧乙基）一1 ，2，4 一三唑 將2 —溴乙基甲基醚（6 · 7ml ，〇 ·〇72 m ◦ 1 )加入一攪拌中以冰冷卻而含有1，2，4 一三嗤 (5.〇g，〇.〇72mol)，碳酸鉀（10g， 〇 ·〇72mo 1)及丙酮（50ml)之懸浮液裡。3 小時後把冷卻浴移開，並於室溫下持續攪拌1 8小時。過 濾反應混合物，把濾液減壓蒸發，再將殘餘物以管柱層析 法利用二氯甲烷：甲醇（9 5 : 5 )爲沖提液在矽膠上純 化而得到澄淸油狀物之標題化合物（5 · 2 g )。 ^ ( C D C 1 3 ) :3.32(3H，s)， 3 · 7 4 ( 2 Η，t )， 4.34(2H，t)， 7 · 9 2 ( 1 Η，s )， 8 · 1 4 ( 1 Η，s )。 LRMS:m/z 128(M+1)+。 ϋ張尺度適用中國國家標準（CNS ) A4規格（21 OX 297公釐）~._238 - (請先閱讀背面之注意事項再填寫本頁)5248〇5 Printed by the Consumer Cooperatives of the Central Bureau of Standards of the Ministry of Economic Affairs A7 B7 V. Description of the invention (235) 7 · 04 (1Η, d), 7 · 1 4 (1Η, m), 7-45 (lH, m), 7 · 8 4 (1 H, s), 8 · 3 9 (1 H, d),. L R M S: m / z 408 (M + 1) +. Preparation Example 6 1 1- (2-methoxyethyl) -1,2,4-triazole Add 2-bromoethyl methyl ether (6.7 ml, 0.072 m ◦ 1) to a stirring to On ice cooling, a suspension containing 1,2,4-triamidine (5.0 g, 0.072 mol), potassium carbonate (10 g, 0.072 mo 1), and acetone (50 ml) was contained. After 3 hours, remove the cooling bath and continue stirring at room temperature for 18 hours. The reaction mixture was filtered, the filtrate was evaporated under reduced pressure, and the residue was purified by column chromatography using dichloromethane: methanol (95: 5) as the eluent on silica gel to obtain the title compound as a clear oil. (5 · 2 g). ^ (CDC 1 3): 3.32 (3H, s), 3 · 7 4 (2 Η, t), 4.34 (2H, t), 7 · 9 2 (1 Η, s), 8 · 1 4 (1 Η , S). LRMS: m / z 128 (M + 1) +. ϋ Zhang scale is applicable to China National Standard (CNS) A4 specification (21 OX 297 mm) ~ ._238-(Please read the precautions on the back before filling this page)

524805 A7 _______^_ B7 五、發明説明（236) ~^ 製備例6 2 5 —經甲基一1 一（2 —甲氧乙基）一1 ，2 ，4、 c請先聞讀背面之注意事¾再填寫本頁) 三口坐 令製備例6 1標題化合物（4 · 3 g，0 · 0 3 4 mo 1)於40%甲醛水溶液（5ml ，0 ·〇98 m 〇 1 )中所形成的溶液在一密封容器中於1 4 0 °C加熱 1 8小時。冷卻後減壓蒸發，再將殘餘物以管柱層析法利 用二氯甲烷：甲醇（9 7 : 3 )爲沖提液於矽膠上純化而 得到油狀物的標題化合物（8 7 % )。 5 ( C D C 1 3 ) :3.30(3H，s)， 3 · 7 6 ( 2 Η，t )， 4 · 0 8 ( 1 Η，s )， 4 · 4 1 ( 2 Η，t )， 4 . 7 8 ( 2 Η，s )， 7 · 8 5 ( 1 Η，s )。 m/z 158 (M+l)+。 經濟部中央標準局員工消費合作社印製 製備例6 3 5 —氯甲基一1 一（2 —甲氧乙基）一1 ，2 ，4 一 三唑鹽酸鹽 將製備例6 2標題化合物（3 · 5 g，0 · 0 2 2 m ο 1 )逐滴加入攪拌中而以冰冷卻之硫醯氯（1 〇 m 1 )裡，然後把冷卻浴移開。令反應混合物於室溫下攪拌5 -239- 本紙張尺度適用中國國家標準（CNS ) A4規格（210Χ 297公釐） 524805 A7 B7 五、發明説明（237) 小時，接著減壓蒸發。將殘餘物與甲苯（5 0 m 1 )共沸 而得黃色油狀之標題化合物（4 · 6 g )。 5 ( C D C 1 a ) :3.32(3H，s)， 3 · 7 9 ( 2 Η，t )， 4 · 5 9 ( 2 Η，t )， 5 . 1 5 ( 2 Η，s )， 8 · 4 〇（1 Η，s )， l〇.〇9(lH，s)。 製備例θ 4 1—〔 1— (2 —甲氧乙基）一1 ，2 ，4 —二口坐一 5 —基〕甲基—5— (2 -正丙氧苯基）一 3 —正丙基— 1，6 —二氫—7Η — 吡唑並〔4，3 — d〕嘧啶一 7 — 酮 由製備例1 2之標題化合物及製備例6 3標題化合物 之自由鹼依製備例1 5 B之步驟製得，呈白色固體（3〇 % )。 本纸張尺度適用中國國家標準（CNS ) A4規格（210X297公釐）-240 _ (讀先閲讀背面之注意事項再填寫本頁)524805 A7 _______ ^ _ B7 V. Description of the invention (236) ~ ^ Preparation example 6 2 5 — Via methyl-1 1- (2-methoxyethyl) -1, 2, 4, 4, c Please read the notes on the back first ¾ Please fill in this page again.) Three mouthfuls of preparation Example 6 1 The title compound (4 · 3 g, 0 · 0 3 4 mo 1) was formed in 40% aqueous formaldehyde solution (5 ml, 0 · 0.098 m 〇1). The solution was heated in a sealed container at 140 ° C for 18 hours. After cooling, it was evaporated under reduced pressure, and the residue was purified by column chromatography using dichloromethane: methanol (97: 3) as the eluent on silica gel to obtain the title compound (87%) as an oil. 5 (CDC 1 3): 3.30 (3H, s), 3 · 7 6 (2 Η, t), 4 · 0 8 (1 Η, s), 4 · 4 1 (2 Η, t), 4.7 8 (2 Η, s), 7 · 8 5 (1 Η, s). m / z 158 (M + 1) +. Printed by the Consumer Cooperative of the Central Standards Bureau of the Ministry of Economic Affairs. Preparation Example 6 3 5 -Chloromethyl-1 1- (2-methoxyethyl) -1,2,4 Triazole hydrochloride will be prepared in Example 6 2 with the title compound ( 3 · 5 g, 0 · 0 2 2 m ο 1) Add dropwise to the thionyl chloride (10 m 1) cooled with ice while stirring, and then remove the cooling bath. Allow the reaction mixture to stir at room temperature for 5 -239- This paper size is in accordance with Chinese National Standard (CNS) A4 (210 × 297 mm) 524805 A7 B7 5. Description of the invention (237) hours, and then evaporated under reduced pressure. The residue was azeotroped with toluene (50 m 1) to give the title compound (4.6 g) as a yellow oil. 5 (CDC 1 a): 3.32 (3H, s), 3 · 7 9 (2 Η, t), 4 · 5 9 (2 Η, t), 5. 1 5 (2 Η, s), 8 · 4 〇 (1 Η, s), 109 (lH, s). Preparation Example θ 4 1— [1— (2-methoxyethyl) -1,2,4-dione 5-methyl] methyl-5— (2-n-propoxyphenyl) -3—n Propyl-1,6-dihydro-7H-pyrazolo [4,3-d] pyrimidin-7-one was prepared from the title compound of Preparation Example 12 and Preparation Example 6 3 The free base of the title compound was prepared according to Preparation Example 1 5 Prepared in step B as a white solid (30%). This paper size applies Chinese National Standard (CNS) A4 specification (210X297 mm)-240 _ (Read the precautions on the back before filling in this page)

-- NJ. \ϊ/ Ν)/ \Μ/ \)y tmmt s t 3)HHH Η Η H 1 3 2 2 2 3 2 /IV /^' /l\ /l\ /l\ /(V D 6 6 〇 4 6 〇 c 1 8 o 8 2 7 ^^-^^ · · · ♦· ΓΟ r-H Ίχ CO 00 CO oo Η 3 /IV 〇 〇 經濟部中央標準局員工消費合作社印製 524805 經濟部中央標隼局員工消費合作社印製 A7 B7 五、發明説明（Z38) 4 · 1 9 ( 2 Η，t )， 4 · 5.6 ( 2 Η ， t )， 6 ·〇〇（2 Η ， s )， 7 ·〇 4 ( 1 Η，d )， 7 · 1 5 ( 1 Η，πι )， 7 · 4 5 ( 1 Η，m )， 7 · 8 4 ( 1 Η，s )， 8 · 4 8 ( 1 Η，d )， 1 1 · 2 〇（1 Η，s )。 LRMS:m/z 452 (Μ+1)+。 製備例6 5 2 —〔1— (2 —甲氧乙基）一1 ，2，4 —三唑一 5 —基〕甲基一 5— (2 —正丙氧苯基）一 3 —正丙基— 1，6 — 二氫一 7Η — d 比 ti坐並〔4，3 - d〕喃π定一 7 — 酮 由製備例1 2之標題化合物及製備例6 3標題化合物 之自由鹼依製備例1 5 B之步驟製得，呈白色固體（2〇 % )。 (5(CDCls)：l.〇3(3H^t)^ 1 · 1 3 ( 3 Η，t )， 1 · 8 3 ( 2 Η，m )， 1 · 9 9 ( 2 Η，m )， 3 · 1 2 ( 2 Η，t )， 本纸張尺度適用中國國家標準（CNS ) Α4規格（210X297公釐）-241 - (請先閱讀背面之注意事項再填寫本頁)-NJ. \ Ϊ / Ν) / \ Μ / \) y tmmt st 3) HHH Η Η H 1 3 2 2 2 3 2 / IV / ^ '/ l \ / l \ / l \ / (VD 6 6 〇4 6 〇c 1 8 o 8 2 7 ^^-^^ · · · ♦ · ΓΟ rH Ίχ CO 00 CO oo Η 3 / IV 〇〇 Printed by the Central Consumers Bureau of the Ministry of Economic Affairs Consumer Cooperatives 524805 Printed by the Consumer Cooperative of the Bureau A7 B7 V. Description of Invention (Z38) 4 · 19 (2 Η, t), 4 · 5.6 (2 Η, t), 6 · 〇 (2 ，, s), 7 · 〇 4 (1 Η, d), 7 · 1 5 (1 Η, π), 7 · 4 5 (1 Η, m), 7 · 8 4 (1 Η, s), 8 · 4 8 (1 Η, d ), 1 1 · 2 0 (1 Η, s). LRMS: m / z 452 (M + 1) +. Preparation Example 6 5 2 — [1— (2-methoxyethyl) —1,2,4 —Triazole-5—yl] methyl-5— (2-n-propoxyphenyl) —3—n-propyl—1,6—dihydro-7Η — d sits more than ti [4,3-d] Nanidine-7-one was prepared from the title compound of Preparation Example 12 and Preparation Example 6 3 as the free base of the title compound according to the procedure of Preparation Example 15B, as a white solid (20%). (5 (CDCls) : 1.03 (3H ^ t) ^ 1 · 1 3 (3 Η, t), 1 · 8 3 (2 Η, m), 1 · 9 9 (2 Η, m), 3 · 1 2 (2 Η, t), this paper size applies to China National Standard (CNS) Α4 specifications ( 210X297 mm) -241-(Please read the precautions on the back before filling this page)

524805 Α7 Β7 經濟部中央標準局員工消費合作社印製 五、發明説明（239) 3 . 3 〇（3 Η，s )， 3 · 7 〇（2 Η，t )， 4 · 1 8 ( 2 Η，t )， 4 · 6 1 ( 2 Η，t )， 5 · 7 8 ( 2 Η，s )， 7 ·〇 4 ( 1 Η，d )， 7 · 1 4 ( 1 Η，m )， 7 · 4 4 ( 1 Η，m )， 7.86(lH，s)， 8 · 3 9 ( 1 Η，d )， l〇.87(lH，s)° L R M S ： m / z 452 (M+1)+。 製備例6 6 1— (4 —甲基一1 ，2，4 —三唑一3 —基）甲基 一 5— (2 —正丙氧苯基）一 3 —正丙基一 1，6 -二氫 一 7 Η — d比π坐並〔4，3 — d〕嘧D定—7 —酮 由製備例12之標題化合物及3—氯甲基一4一甲基 —1，2，4 —三唑鹽酸鹽（Chem. Pharm. Bull.，1 994, 11, 85)之自由鹼依製備例1 5 B之步驟製得，呈白色固 體（3 4 % )。 (5(CDCl3):l.〇0(3H，t)， 1 · 1 8 ( 3 Η，t )， 1 · 8 5 ( 2 Η ，m )， (讀先閲讀背面之注意事項再填寫本頁) _裝· -一口 •Φ 本紙張尺度適用中國國家標準（CNS ) A4規格（210X297公釐）-242 - 524805 經濟部中央標準局員工消費合作社印裂 A7 B7 五、發明説明（240) 2 ·〇 3 ( 2 Η，m )， 2 · 9 2 ( 2 Η，t )， 3 . 7 3 ( 3 Η，s )， 4 · 2 〇（2 Η，t )， 6 · 0 5 ( 2 Η，s )， 7 ·〇 6 ( 1 Η，d )， 7 · 1 6 ( 1 Η，m )， 7 · 4 8 ( 1 Η，m )， 8 · 1 〇（1 Η，s )， 8 · 5 〇（1 Η，d )， 11.28(lH，s)。 LRMS :m/z 408 (M+l)+。 製備例6 7 1— (1 ，2，4 —噚二唑—3 —基）甲基一5 —( 2 -正丙氧苯基）一 3 —正丙基—1，6 —二氫—7H -吡唑並〔4，3 — d〕嘧啶—7 —酮 由製備例1 2之標題化合物及3 -氯甲基一1 ，2， 4 一鸣二唑依製備例1 5D之步驟製得，呈灰色固體（2 4 % )。 5(CDCl3):l.〇2(3H，t)， 1 · 1 8 ( 3 Η，t )， 1 · 8 8 ( 2 Η，m )， .2 . 0 0 ( 2 Η ^ m )， 本纸張尺度適用中國國家標準（CNS ) Α4規格（21 ΟΧ 297公釐）~[^43 - (讀先閲讀背面之注意事項再填寫本頁)524805 Α7 Β7 Printed by the Consumer Cooperatives of the Central Standards Bureau of the Ministry of Economic Affairs V. Invention Description (239) 3. 30 (3 （, s), 3 · 7 〇 (2 Η, t), 4 · 1 8 (2 Η, t), 4 · 6 1 (2 Η, t), 5 · 7 8 (2 Η, s), 7 · 〇 4 (1 Η, d), 7 · 1 4 (1 Η, m), 7 · 4 4 (1 Η, m), 7.86 (lH, s), 8.39 (1 Η, d), 10.87 (lH, s) ° LRMS: m / z 452 (M + 1) +. Production Example 6 6 1— (4-methyl-1,2,4-triazol-3-yl) methyl-5— (2-n-propoxyphenyl) —3—n-propyl-1,6- Dihydro-7 Η — d sat with π and [4,3 — d] pyrimidine-7-one was prepared from the title compound of Preparation Example 12 and 3-chloromethyl-4methyl —1,2,4 — The free base of triazole hydrochloride (Chem. Pharm. Bull., 1 994, 11, 85) was prepared according to the procedure of Preparation Example 15B, and it appeared as a white solid (34%). (5 (CDCl3): 1.00 (3H, t), 1 · 1 8 (3 Η, t), 1 · 8 5 (2 Η, m), (Read the precautions on the back before filling in this page ) _Package · -One bit • Φ This paper size is applicable to Chinese National Standard (CNS) A4 (210X297 mm) -242-524805 Employees' Cooperatives of the Central Standards Bureau of the Ministry of Economic Affairs printed A7 B7 V. Description of the invention (240) 2 · 〇3 (2 Η, m), 2 · 9 2 (2 Η, t), 3. 7 3 (3 Η, s), 4 · 2 〇 (2 Η, t), 6 · 0 5 (2 Η, s), 7 · 〇6 (1 Η, d), 7 · 16 (1 Η, m), 7 · 4 8 (1 Η, m), 8 · 1 〇 (1 Η, s), 8 · 5 〇 (1 Η, d), 11.28 (lH, s). LRMS: m / z 408 (M + 1) +. Preparation Example 6 7 1— (1,2,4-dioxadiazol-3-yl) methyl A 5-n- (2-n-propoxyphenyl) -3-n-propyl-1,6-dihydro-7H-pyrazolo [4,3-d] pyrimidin-7-one was prepared from Preparation Example 1 2 The title compound and 3-chloromethyl-1,2,4-dioxadiazol were prepared according to the steps of Preparation 5D of Preparation 1 as a gray solid (24%). 5 (CDCl3): 1.02 (3H, t ), 1 · 1 8 (3 Η, t), 1 · 8 8 (2 Η, m), .2. 0 0 (2 Η ^ m), this paper size applies to China National Standard (CNS) Α4 specification (21 〇 × 297 mm) ~ [^ 43-(Read the first read on the back (Please fill in this page again)

524805 經濟部中央標準局員工消費合作社印製 Α7 Β7 五、發明説明（241) 2 · 9 7 ( 2 Η，t )， 4 · 1 9 ( 2 Η，t )， 6 .〇 2 ( 2 Η，s )， 7 ·〇 4 ( 1 Η，d )， 7 · 1 6 ( 1 Η，m )， 7 · 4 6 ( 1 Η，m )， 8.52(lH，d)， 8 · 6 6 ( 1 H，s )， 11.28(lH，s)。 LRMS:m/z 395 (M+1)+。 製備例6 8 2 —苄氧羰甲基—5 —（2 —正丙氧苯基）一 3 —正 丙基—2，6 —二氣一 7H -吼坐並〔4，3 — d〕嘧D定 —7 —酮 由製備例1 2之標題化合物及溴乙酸苄酯依製備例 15B之步驟製得，呈黃色固體（45%)。 5 ( C D C 1 a ) :l.〇〇（3H，t)， 1 · 1 4 ( 3 Η，t )， 1 · 8 1 ( 2 Η，m )， 2 . Ο Ο ( 2 Η > m )， 2 . 8 9 ( 2 Η > t )， 4 · 1 8 ( 2 Η，t )， 5 · 1 7 ( 2 Η ， s )， 本紙張尺度適用中國國家標準（CNS ) Α4規格（210Χ 297公釐）_ 244 - (讀先閱讀背面之注意事項再填寫本頁)524805 Printed by the Consumer Cooperatives of the Central Standards Bureau of the Ministry of Economic Affairs A7 Β7 V. Description of the invention (241) 2 · 9 7 (2 Η, t), 4 · 1 9 (2 Η, t), 6.02 (2 Η, s), 7 · 〇4 (1 Η, d), 7 · 16 (1 Η, m), 7 · 4 6 (1 Η, m), 8.52 (lH, d), 8 · 6 6 (1 H , S), 11.28 (lH, s). LRMS: m / z 395 (M + 1) +. Preparation Example 6 8 2 -Benzyloxycarbonylmethyl-5-(2-n-propoxyphenyl) -3-n-propyl-2,6-digas-7H D-D--7-one was prepared from the title compound of Preparation 12 and benzyl bromoacetate by the procedure of Preparation 15B as a yellow solid (45%). 5 (CDC 1 a): 1.0 (3H, t), 1 · 1 4 (3 t, t), 1 · 8 1 (2 Η, m), 2. 〇 〇 (2 Η > m) , 2. 8 9 (2 Η > t), 4 · 1 8 (2 Η, t), 5 · 1 7 (2 Η, s), this paper size applies Chinese National Standard (CNS) Α4 specification (210 × 297 Mm) _ 244-(Read the notes on the back before filling this page)

524805 A7 B7 經濟部中央標準局員工消費合作社印掣 五、發明説明（242) 5 · 2 3 ( 2 Η，s )， 7 · 0 6 ( 1 Η，d )， 7 . 13 (lH?m)， 7.36(5H，m)， 7 · 4 6 ( 1 H，m )， 8 . 4 1 ( 1 H，d )， 1〇·87 (lH，s)。 製備例6 9 2-羧甲基一5—(2-正丙氧苯基）〜3一正丙基 一 2，6 —一氣—7H — 口比口坐並〔4，3〜d〕嚼d定—7 一酮 . 將1 0%銷（於木炭上，2 Omg )加入含有製備例 68標題化合物（207mg ，0 · 45mm〇1)與乙 酸乙酯（2 5 m 1 )之溶液裡，令此混合物於1 3 8 k P a ( 2 0 p s i )之氫氣下攪拌2 0小時，然後過濾 。把濾液減壓蒸發而得到黃色粉狀之標題化合物（9 5 % )° 5 ( D M S 0 d 6 ):〇·93(6Η，ιη)， 1.71(4H，m)， 2 · 8 4 ( 2 Η，t )， 4 · 0 3 ( 2 Η，t )， 5 · 2 1 ( 2 Η，s )， 7.09 (lH，m)， 本紙張尺度適用中國國家標準（CNS ) A4規格（21〇X29*7公釐）_ 245 (讀先閱讀背面之注意事項再填寫本頁)524805 A7 B7 Printed by the Consumer Cooperatives of the Central Standards Bureau of the Ministry of Economic Affairs V. Description of the Invention (242) 5 · 2 3 (2 Η, s), 7 · 0 6 (1 Η, d), 7. 13 (lH? M) , 7.36 (5H, m), 7.46 (1H, m), 8.41 (1H, d), 10.87 (lH, s). Preparation Example 6 9 2-carboxymethyl-5— (2-n-propoxyphenyl) ~ 3—n-propyl—2,6—one gas—7H — mouth to mouth and [4,3 ~ d] chewing d Ding-7 monoketone. 10% pin (on charcoal, 2 Omg) was added to a solution containing the title compound of Preparation 68 (207 mg, 0.45 mm) and ethyl acetate (2 5 m 1). This mixture was stirred under hydrogen at 138 kPa (20 psi) for 20 hours and then filtered. The filtrate was evaporated under reduced pressure to give the title compound (95%) as a yellow powder (95%) (DMS 0 d6): 0.93 (6Η, ιη), 1.71 (4H, m), 2 · 8 4 (2Η , T), 4 · 0 3 (2 Η, t), 5 · 2 1 (2 Η, s), 7.09 (lH, m), this paper size applies Chinese National Standard (CNS) A4 specification (21〇X29 * 7 mm) _ 245 (Read the precautions on the back before filling in this page)

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、1T 524805 經濟部中央標準局員工消費合作社印製 A7 B7 五、發明説明（ 243) 7 · 1 6 ( 1 Η，d )， 7 · 4 8 ( 1 Η，m )， 7 · 6 9 ( 1 Η，d )， 11.52(lH，s) 〇 LRMS:m/z 371 (·Μ +1) +。 製備例7 Ο Ν —第三丁氧鑛基—Ν>— {2 —〔5 —（2 -正丙 氧本基）—3 —正丙基—2，6 —二氨一 7Η — d比卩坐並〔 4，3 — d〕嘧啶—7 —酮—2 —基〕乙醯基}肼 將草醯氯（0 · 33ml ，3 · 8mmo 1)逐滴加 入一攪拌中且以冰冷卻而由製備例6 9標題化合物（ 〇· 7〇g ，1 · 9mmo 1)於二氯甲烷（7ml )中 所形成的懸浮液裡，然後添加二甲基甲醯胺（2滴），把 冷卻浴移開，於室溫下攪拌反應混合物2小時，然後減壓 蒸發。令殘餘物與二氯甲烷（3 0 m 1 )共沸而得到所需 之醯氯，呈黃色固體。 將此中間物加入一個攪拌中且含有肼甲酸第三丁酯（ 〇.25g，l. 9mm 〇 1)，三乙胺（〇.4.〇ml ，2 · 8mmo 1)及二氯甲烷（i〇mi)之溶液裡。 在室溫下攪拌2小時後用5 %檸檬酸水溶液（2 0 m 1 ) 洗之，此洗液以二氯甲烷（5 0 m 1 )萃取，有機溶液合 倂後乾燥（M g S 0 4 )後減壓蒸發。以管柱層析法利用己 烷：乙酸乙酯（1 : 1至1 : 2 )之沖提梯度加以純化而 本紙張尺度適用中國國家標準（CNS ) Α4規格（21 ΟΧ 297公釐）_ 246 |裝一 (請先閱讀背面之注意事項再填寫本頁, 1T 524805 Printed by the Consumer Cooperatives of the Central Standards Bureau of the Ministry of Economic Affairs A7 B7 V. Description of the invention (243) 7 · 1 6 (1 Η, d), 7 · 4 8 (1 Η, m), 7 · 6 9 (1 H, d), 11.52 (lH, s). LRMS: m / z 371 (· M +1) +. Preparation Example 7 Ο Ν—The third butoxy group based—N > — {2 — [5 — (2 -n-propoxybenzyl) -3—n-propyl-2,6—diamine-7 一 — d ratio 卩Sit and [4,3-d] pyrimidin-7-keto-2-yl] ethenyl} hydrazine. Add chlorchloride (0.33ml, 3.8mmo 1) dropwise into a stirrer and cool with ice. Preparation Example 6 9 A suspension of the title compound (0.70 g, 1.9 mmo 1) in dichloromethane (7 ml) was added to dimethylformamide (2 drops), and the cooling bath was transferred. On, the reaction mixture was stirred at room temperature for 2 hours and then evaporated under reduced pressure. The residue was azeotroped with dichloromethane (30 m 1) to give the desired ammonium chloride as a yellow solid. This intermediate was added to a stir and contained tert-butyl hydrazine formate (0.25 g, 1.9 mm 〇1), triethylamine (0.4.00 ml, 2.8 mmo 1) and dichloromethane (i 〇mi)。 Solution). After stirring at room temperature for 2 hours, it was washed with a 5% citric acid aqueous solution (20 m 1). The washing solution was extracted with dichloromethane (50 m 1). The organic solution was combined and dried (M g S 0 4 ) And evaporated under reduced pressure. Purified by column chromatography using a gradient of hexane: ethyl acetate (1: 1 to 1: 2). This paper is sized to the Chinese National Standard (CNS) A4 (21 〇 × 297 mm) _ 246 | Pack one (Please read the notes on the back before filling in this page

、1T •Φ 524805 A7 B7 五、發明説明（244) 得到呈橙色固體之標題化合物（0 · 2 9 g )。 5(CDCl3):l.〇6(3H，t)， 1 · 1 5 ( 3 Η，t )， 1 · 4 4 ( 9 Η，s )， 1.88(2H，m)， 2 ·〇 Ο ( 2 Η，m )， 3 . Ο 2 ( 2 Η，t )， 4.17(2H，t)， 5 · 2 Ο ( 2 Η，s )， 6 · 5 9 ( 1 Η，s )， 7 ·〇 4 ( 1 Η，d )， 7.12(lH，m)， 7 · 4 4 ( 1 Η，m )， 8 · 4 Ο ( 1 Η，d )， 8 . 7 2 ( 1 Η，s )， l〇.96(lH，s)° L R Μ S ： m / z 485 (M+1)+。 經濟部中央標準局員工消費合作社印製 (請先閱讀背面之注意事項再填寫本頁) 製備例7 1 N— {2 -〔5 -（2 —正丙氧苯基）—3 —正丙基 —2，6 —二氫—7H - 吡唑並〔4，3 — d〕嘧啶一7 一酮—2 —基〕乙醯基}肼鹽酸鹽 令一於攪拌中且以冰冷卻而含製備例7 0標題化合物 (〇· 28g ，〇· 58mm〇1)及二氯甲烷（5ml 本紙張尺度適用中國國家標準（CNS ) A4規格（210X297公釐） 經濟部中央標準局員工消費合作社印製 524805 A7 _____B7_ 五、發明説明（245) )之溶液呈氯化氫飽和狀態，然後把冷卻浴移開。於室溫 下攪拌此反應混合物2小時，接著減壓蒸發而得到黃色固 體之標題化合物（0 · 2 2 g )。 5 ( D M S 0 d 6 ) :0.95 (6H，m)， 1 · 7 2 ( 4 Η，m )， 2 · 8 9 ( 2 Η，t )， 4.〇2(2H，t)， 5.28(2H，s)， 7 · 0 6 ( 1 H，m )， 7 · 1 6 ( 1 H，d )， 7 · 4 8 ( 1 H，m )， 7 . 6 8 ( 1 H，d )， 11.58(2H，s)。 LRMS :m/z 3 8 5 (M+l)+。 製備例7 2 2 —（3 —甲基一1 ，2，4 一三唑一5 —基）甲基 —5— (2 -正丙氧苯基）—3 —正丙基一 2，6 —二氫 一 7 Η - d比哩並〔4，3 - d〕嘧D定一 7 —酮 將含有甲氧化鈉（62mg ，1 · 16πιιη〇1)及 乙醇（2m 1 )之溶液加入一攪拌中而含有乙脒鹽酸鹽（ 82m，〇 · 87mmo 1)及乙醇之溶液裡，·於室溫 下攪拌4 5分鐘。1T • Φ 524805 A7 B7 V. Description of the invention (244) The title compound (0 · 2 9 g) was obtained as an orange solid. 5 (CDCl3): 1.06 (3H, t), 1 · 15 (3Η, t), 1.4 · 4 (9Η, s), 1.88 (2H, m), 2 · 〇〇 (2 Η, m), 3. 〇 2 (2 Η, t), 4.17 (2H, t), 5 · 2 Ο (2 Η, s), 6 · 5 9 (1 Η, s), 7 · 〇 4 ( 1 Η, d), 7.12 (lH, m), 7 · 4 4 (1 m, m), 8 · 4 〇 (1 Η, d), 8.7 2 (1 Η, s), 10.96 (lH, s) ° LR M S: m / z 485 (M + 1) +. Printed by the Consumers' Cooperative of the Central Bureau of Standards of the Ministry of Economic Affairs (please read the precautions on the back before filling this page) Preparation Example 7 1 N— {2-[5-(2—n-propoxyphenyl) —3—n-propyl —2,6 —dihydro-7H-pyrazolo [4,3-d] pyrimidin-7-one-keto-2-yl] ethenyl} hydrazine hydrochloride, prepared by stirring and cooling with ice. Example 7 0 The title compound (.28g, 0.58mm) and dichloromethane (5ml) This paper size applies the Chinese National Standard (CNS) A4 specification (210X297mm) Printed by the Consumer Cooperative of the Central Standards Bureau of the Ministry of Economic Affairs A7 _____B7_ 5. The solution of the invention (245)) is saturated with hydrogen chloride, then remove the cooling bath. The reaction mixture was stirred at room temperature for 2 hours, and then evaporated under reduced pressure to give the title compound (0.22 g) as a yellow solid. 5 (DMS 0 d 6): 0.95 (6H, m), 1 · 7 2 (4 Η, m), 2 · 8 9 (2 Η, t), 4.〇2 (2H, t), 5.28 (2H , S), 7 · 0 6 (1 H, m), 7 · 16 (1 H, d), 7 · 4 8 (1 H, m), 7. 6 8 (1 H, d), 11.58 ( 2H, s). LRMS: m / z 3 8 5 (M + l) +. Preparation Example 7 2 2 — (3-methyl-1,2,4-triazol-5-yl) methyl-5— (2-n-propoxyphenyl) -3—n-propyl-2,6— Dihydro-7 Η-d than mile and [4,3-d] pyrimidine D-one 7-one Add a solution containing sodium methoxide (62mg, 1.16πιηη1) and ethanol (2m 1) to a stirring On the other hand, in a solution containing acetamidine hydrochloride (82m, 0.887mo 1) and ethanol, stir at room temperature for 4 5 minutes.

接著把甲氧化鈉（3〇m g ，〇 · 5 8 m m ο 1 )力D 本紙張尺度適用中國國家標準（CMS ) A4規格（210X297公釐）_ 248 _ (讀先閱讀背面之注意事項再填寫本頁)Then apply sodium methoxide (30mg, 0.58 mm ο 1) force D. This paper size applies the Chinese National Standard (CMS) A4 specification (210X297 mm) _ 248 _ (read the precautions on the back before filling (This page)

524805 A7 ___B7 經濟部中央標準局員工消費合作社印繁 五、發明説明（ 246) 入 —. 含有 製 備 例 7 1 標 題 化合 物 ( 2 2 0 mg 〇 • 5 8 m m 〇 1 ) 及 乙 醇 ( 4 m 1 ) 之 攪 拌 縣 浮 液裡 ， 再 將 此 混 合 物 加 入 先 -u·· 刖 配 製 好 的 乙 脒乙 醇 溶 液 中 〇 令反 應 混 合 物 攪 拌 迴 流 7 2 小 時 冷 卻 後 以水 ( 1 5 m 1 )稀 釋 ， 然 後 用 乙 酸 乙 酯 ( 總 量 4 0 m 1 )對 所得 混 合 物 進行 萃 取 y 有 機 溶 液 經 合倂 並 乾 燥 ( N a 2 S 1 0 , 1 ) 後 〖減壓蒸發， 得 1的 7黃 色 油 狀 物 以 管 柱 層 析 法 利 用乙 醚 ； 甲 醇 ( 9 7 : 3 至 9 0 1 〇 ) 之 沖 提 梯度於矽 膠上 純 化 而 得 到 呈白 色 固 體 之 標 題 化 合 物 ( 1 2 〇 m g ) 〇 5 ( C D C 1 3 , ) 1 • 〇2 ( 3 ] t )， 1 • 1 2 ( 3 Η 5 t ) 1 • 8 5 ( 2 Η m ) 1 ♦ 9 9 ( 2 Η ， m ) 2 • 4 1 ( 3 Η 9 s ) 3 • 0 7 ( 2 Η t ) 4 • 1 6 ( 2 Η t ) 5 • 6 0 ( 2 Η ? s ) 7 • 〇 2 ( 1 Η J d ) 7 • 1 〇 ( 1 Η 5 m ) ? 7 • 4 2 ( 1 Η 5 m ) 8 • 3 9 ( 1 Η 5 d ) ， 1 〇 • 9 3 ( 1 Η > s ) 〇 L R Μ S ； m / Ζ 4 〇 8 ( Μ + 1 ) + 〇 (請先閱讀背面之注意事項再填寫本頁) 訂524805 A7 ___B7 Yin Fan, a Consumer Cooperative of the Central Standards Bureau of the Ministry of Economic Affairs, 5. Description of the Invention (246) Included.-Contains Preparation Example 7 1 The title compound (220 mg 0 5 8 mm 0 1) and ethanol (4 m 1) Stir the county float, and then add this mixture to the -u ·· 刖 prepared acetic acid ethanol solution. Allow the reaction mixture to stir and reflux for 7 2 hours, then cool it with water (15 m 1), and then dilute with Ethyl acetate (total 40 m 1) was used to extract the resulting mixture. The organic solution was combined and dried (Na 2 S 1 0, 1), and then evaporated under reduced pressure to obtain 1 of 7 yellow oil. Chromatography uses diethyl ether; a gradient of methanol (97: 3 to 9101) is purified on silica gel to give the title compound (120 mg) as a white solid (CDC 1 3,) 1 • 〇2 (3] t), 1 • 1 2 (3 Η 5 t) 1 • 8 5 (2 Η m) 1 ♦ 9 9 (2 ，, m) 2 • 4 1 (3 Η 9 s) 3 • 0 7 (2 Η t) 4 • 1 6 (2 Η t) 5 • 6 0 (2 Η? S) 7 • 〇2 (1 Η J d) 7 • 1 〇 (1 Η 5 m)? 7 • 4 2 (1 Η 5 m) 8 • 3 9 (1 Η 5 d), 1 〇 • 9 3 (1 Η > s) LR M S; m / ZZ 4 〇8 (Μ + 1) + 〇 (Please read the notes on the back before filling this page) Order

本紙張尺度適用中國國家標準（CNS ) A4規格（210X297公釐）-249 - 524805 經濟部中央標準局員工消費合作社印^ A7 B7 五、發明説明（247 ) 製備例7 3 2 —氰甲基一 5— (2 —正丙氧苯基）一 3 —正丙基 一 2，6 -二氫—7H - 吡唑並〔4，3 - d〕嘧啶一 7 一酮 將2 Μ雙（三甲矽烷基）胺化鈉的四氫呋喃溶液（ 4 · 42ml ，8 · 8mmo 1 )加入一攪拌中且以冰冷 卻而由製備例1 2標題化合物（2 · 3 g，7 . 4 m m ο 1 )於四氫呋喃（2 5 m 1 )中所形成的溶液裡， 攪拌3 0分鐘後冷卻至大約- 7 0 °C ·接著逐滴添加溴乙 腈（0.54ml ，7.7mmol)，移開冷卻浴，然 後在2 0小時後小心地用甲醇（5 m 1 )中止反應混合物 ，再減遷蒸發。殘餘物以管柱層析法利用二氯甲烷：甲醇 (9 9 : 1至9 5 : 5 )之沖提梯度於矽膠上純化，然後 以己烷：乙酸乙酯進行結晶而得到標題化合物（1 . 8 9 g )，呈白色固體。 元素分析實測値：C，6 4 · 8 4 ; Η，5 · 9 8 ; N， 19 · 71 。C19H21N5〇2計算値 C，64 · 94 ； Η，6·〇2;Ν，19.93%。 5(CDCl3):1.12(6H，m)， 1 · 9 8 ( 4 Η，m )， 3 ·〇 8 ( 2 Η，t )， 4.20(2H，t)， 5 · 2 6 ( 2 H，s )， 7 · 0 5 ( 1 H ，d )， 本紙張尺度適用中國國家標準（CNS ) A4規格（210X297公釐）· 250 - (讀先閱讀背面之注意事項再填寫本頁) 、τThis paper size applies to China National Standard (CNS) A4 (210X297 mm) -249-524805 Printed by the Consumer Cooperatives of the Central Standards Bureau of the Ministry of Economic Affairs ^ A7 B7 V. Description of the Invention (247) Preparation Example 7 3 2 —Cyanomethyl-1 5- (2-n-propoxyphenyl) -3-n-propyl-2,6-dihydro-7H-pyrazolo [4,3-d] pyrimidin-7 monoketone 2 M bis (trimethylsilyl) ) Sodium aminated tetrahydrofuran solution (4.42 ml, 8.8 mmo 1) was added to a stirring and cooled with ice to prepare the title compound (2 · 3 g, 7.4 mm ο 1) from Preparation Example 12 in tetrahydrofuran (2 5 m 1) of the solution formed, stirred for 30 minutes and then cooled to about-70 ° C · Then bromoacetonitrile (0.54 ml, 7.7 mmol) was added dropwise, the cooling bath was removed, and after 20 hours The reaction mixture was discontinued carefully with methanol (5 m 1), and then evaporated by decrement. The residue was purified by column chromatography on a silica gel using a gradient of dichloromethane: methanol (99: 1 to 9 5: 5) and then crystallized from hexane: ethyl acetate to give the title compound (1 8 9 g) as a white solid. Elemental analysis: 値: C, 6 4 · 8 4; Η, 5 · 9 8; N, 19 · 71. C19H21N502 calculated 値 C, 64.94; Η, 6.02; N, 19.93%. 5 (CDCl3): 1.12 (6H, m), 1.98 (4 Η, m), 3.08 (2 Η, t), 4.20 (2H, t), 5.20 (2H, s) ), 7 · 0 5 (1 H, d), this paper size applies Chinese National Standard (CNS) A4 specification (210X297 mm) · 250-(Read the precautions on the back before filling this page), τ

524805 經濟部中央標準局員工消費合作社印製 Α7 Β7 五、發明説明（248 ) 7 · 1 6 ( 1 Η，m )， 7 · 4 8 ( 1 Η，m )， 8 · 4 2 ( 1 Η，d )， ll.〇〇（lH，s) 〇 LRMS:m/z 703 (M+1) +。 製備例7 4 2 -〔5 -（2 -正丙氧苯基）一 3 -正丙基一 2， 6 —二氫一 7H —卩比d坐並〔4，3 — d〕嘧υ定—7 —酮一 2 —基〕acetamidoxime 將碳酸鈉（1 9 9 m g，1 · 9 m m ο 1 )及羥基胺 鹽酸鹽（2 6 〇mg ，3 · 7mmo 1)加入一攪拌中而 由製備例73標題化合物（878mg，2 · 5mm〇1 )於5 0 %乙醇水溶液（1 〇 m 1 )中所形成之懸浮液裡 。把混合物加熱迴流1 8小時，然後冷卻。析出的沈澱物 收集後以水（3 0 m 1 )洗之，真空乾燥，而得到呈白色 固體之標題化合物（9 0 2mg)。 元素分析實測値：C，5 9 · 2 3 ; Η，6 . 2 6 ; N， 21 · 51 °C19H24N6〇3 計算値 C，59 . 36 ； Η，6·29;Ν，21·86%。 (5 (D Μ S 〇 d 6 )： 0 1 • 6 3 ( 4 Η ，m )， 2 • 9 2 ( 2 Η ，t )， 4 •〇 4 ( 2 Η ，t )， 本紙張尺度適用中國國家標準（CNS ) Α4規格（210X297公釐）-251 - (請先閱讀背面之注意事項再填寫本頁) 訂 ♦ 5248〇5 經濟'那中央榡準局員工消費合作社印製 A7 B7 五、發明説明（249 ) 4 · 9 4 ( 2 Η，s )， 5 · 4 8 ( 2 Η，s )， 7.〇6(lH，m)， 7 · 1 7 ( 1 Η，d )， 7 · 4 6 ( 1 Η，m )， 7 · 6 8 ( 1 Η，d )， 9 · 9 3 ( 1 Η，s )， ll.49(lH，s)。 L R M S ： m / z 385 (M+1)+。 製備例7 5 〇一乙醯基一2 —〔5 —（2 —正丙氧苯基）一 3 — 正丙基—2，6 -二氫—7H -吡唑並〔4，3 - d〕嘧 11 定—7 一酮—_ 2 —基〕acetamidoxime 將乙酐（336// 1 ，3 · 38mmo 1)加入含有 製備例74標題化合物（684mg，1 · 69mmo 1 )與四氫呋喃（5 m 1 )之溶液裡，把混合物攪拌迴流3 小時，然後冷卻。產生的沈澱物收集後以乙醚（2 0 m 1 )洗之再真空乾燥而得白色固狀之標題化合物（6 5 0 mg)。 元素分析實測値：C，5 9 · 0 2 ; Η，6 . 0 9 ; N ’ 19 · 58。C21H26N6〇4計算値 C，59 · 14 ; Η，6 · 1 5 ; N，1 9 · 7 1 %。 δ ( D M S 0 d 6 ):〇.95(6H，m)， 本紙張尺度適用中國國家標準（CNS ) A4規格（21 OX 297公釐）_ 252 _ (請先閲讀背面之注意事項再填寫本頁)524805 Printed by the Consumer Cooperatives of the Central Standards Bureau of the Ministry of Economic Affairs Α7 Β7 V. Description of the invention (248) 7 · 16 (1 Η, m), 7 · 4 8 (1 Η, m), 8 · 4 2 (1 Η, d), 110.0 (lH, s). LRMS: m / z 703 (M + 1) +. Preparation Example 7 4 2-[5-(2-n-propoxyphenyl) -3-n-propyl-2, 6-dihydro-7H- 卩 than d sat and [4,3-d] pyridine- 7-keto-2-yl] acetamidoxime Add sodium carbonate (19 mg, 1.9 mm ο 1) and hydroxylamine hydrochloride (260 mg, 3.7 mmo 1) to a stirring solution, and prepare the preparation example 73. The title compound (878 mg, 2.5 mmol) was suspended in a 50% ethanol aqueous solution (10 ml). The mixture was heated at reflux for 18 hours and then cooled. The precipitate was collected, washed with water (30 m 1), and dried under vacuum to obtain the title compound (920 mg) as a white solid. Elemental analysis: 値: C, 5 9 · 2 3; Η, 6. 2; N, 21 · 51 ° C 19H24N60 〇 Calculate 値 C, 59. 36; Η, 6.29; N, 21 · 86%. (5 (DMS 〇d 6): 0 1 • 6 3 (4 Η, m), 2 • 9 2 (2 Η, t), 4 • 〇4 (2 ，, t), this paper scale applies to China National Standard (CNS) Α4 Specification (210X297 mm) -251-(Please read the precautions on the back before filling out this page) Order ♦ 5248〇5 Economy 'that printed by the Central Consumers ’Bureau Consumer Cooperative A7 B7 V. Invention Explanation (249) 4 · 9 4 (2 Η, s), 5 · 4 8 (2 Η, s), 7.〇6 (lH, m), 7 · 1 7 (1 Η, d), 7 · 4 6 (1 Η, m), 7 · 6 8 (1 Η, d), 9 · 9 3 (1 Η, s), ll.49 (lH, s). LRMS: m / z 385 (M + 1) +。 Production Example 7 5 〇 一 ethylenyl-2 — [5 — (2-n-propoxyphenyl) — 3 —n-propyl-2,6-dihydro-7H-pyrazolo [4,3- d] pyrimidine-7-one- 2 -yl] acetamidoxime Add acetic anhydride (336 // 1, 3 · 38mmo 1) to the title compound of Preparation 74 (684mg, 1.69mmo 1) and tetrahydrofuran (5 m 1), the mixture was stirred at reflux for 3 hours, and then cooled. The resulting precipitate was collected and washed with ether (20 m 1). The title compound (650 mg) was obtained by air-drying as a white solid. Elemental analysis: 値: C, 5 9 · 0 2; Η, 6. 0; N '19 · 58. C21H26N60. Calculate 値 C, 59 · 14; Η, 6 · 15; N, 19 · 7 1%. Δ (DMS 0 d 6): 0.95 (6H, m), this paper size applies Chinese National Standard (CNS) A4 specification ( 21 OX 297 mm) _ 252 _ (Please read the notes on the back before filling this page)

524805 經濟部中央標準局員工消費合作社印製 A7 _____B7 五、發明説明（250) ~ ' ^ 1 · 6 6 ( 4 Η，m )， 2 ·〇 3 ( 3 Η，s )， 2 · 9 5 ( 2 Η，t )， 4 · 0 4 ( 2 Η，t )， 5.05(2H，s)， 6 · 5 9 ( 2 H，s )， 7 · 0 6 ( 1 H，m )， 7 . 1 6 ( 1 H，d )， 7 · 4 7 ( 1 H，m )， 7 · 6 8 ( 1 H，d )， 11.52(lH，s)° LRMS :m/z 427 (M+l)+。 製備例7 6 2— (5 —甲基一 1 ，2，4 —噚二唑一 3 一基）甲 基一 5 — (2 —正丙氧苯基）一 3 一正丙基—2，6 —二 氫一 7H —吡唑並〔4，3 — d〕嘧啶—7 —酮 將製備例7 5標題化合物（6 3 〇 m g，工· 5 〇 mmol)與雙（2 —甲氧乙）醚（5ml)的溶液攪拌 迴流5小時’冷卻後減壓蒸發。殘餘物以管柱層析法利用 己烷：乙酸乙酯（3 4 : 6 6 )爲沖提液於矽膠上純化而 得到固態標題化合物（5 2 0 m g )。 元素分析實測値：C，6 1 · 4 0 ; Η，5 · 8 6 ; N， 2〇· 28 。C21H24n6〇3計算値 C ，61 · 75 ; 本紙張尺度適用中國國家標率（CNS ) A4規格（21 Οχ 297公楚）_ 253 - (請先閱讀背面之注意事項再填寫本頁) 隊裝· 訂 Φ 經濟部中央標準局員工消費合作社印製 524805 A7 B7 五、發明説明（251) Η，5·92;Ν，2〇·57%。 (5 ( D M S 0 d 6 ):〇.95(6H，m)， 1 · 7 4 ( 4 Η，m )， 2 · 5 8 ( 3 Η，s )， 2 · 9 8 ( 2 Η，t )， 4 ·〇 3 ( 2 Η，t )， 5 · 7 6 ( 2 Η，s )， 7 ·〇 6 ( 1 Η，m )， 7 · 1 6 ( 1 Η，d )， 7 · 4 5 ( 1 Η，m )， 7 · 6 6 ( 1 Η，d )， 11.55(lH，s)° L R M S ： m / z 4〇9(M+1)+。 製備例7 7 2 —氰甲基一 5 — (2 —乙氧苯基）一3 —正丙基一 2，6 —二氫一 7H —吡唑並〔4，3 — d〕嘧啶一 7 — 酮 由製備例1 4之標題化合物及溴乙腈依製備例7 3之 步驟製得，呈固體（7 3 % )。 5 ( C D C 1 a ) :l,l〇（3H，t)， 1 · 6 〇（3 Η，t )， 1 · 9 5 ( 2 Η，m )， 3 · 0 8 ( 2 Η，t )， 本紙張尺度適用中國國家標準（CNS ) Α4規格（210X297公釐）~- 254 -~ (讀先閲讀背面之注意事項再填寫本頁)524805 Printed by the Consumer Cooperative of the Central Standards Bureau of the Ministry of Economic Affairs A7 _____B7 V. Description of the invention (250) ~ '^ 1 · 6 6 (4 Η, m), 2 · 〇3 (3 Η, s), 2 · 9 5 ( 2 Η, t), 4 · 0 4 (2 Η, t), 5.05 (2H, s), 6 · 5 9 (2 H, s), 7 · 0 6 (1 H, m), 7. 1 6 (1 H, d), 7 · 4 7 (1 H, m), 7 · 6 8 (1 H, d), 11.52 (lH, s) ° LRMS: m / z 427 (M + 1) +. Production Example 7 6 2— (5-methyl-1,2,4—fluoradiazol-3 3-yl) methyl-5— (2-n-propoxyphenyl) -3—n-propyl-2,6 —Dihydro-7H—pyrazolo [4,3-d] pyrimidin-7-one. The title compound of Preparation Example 7 (630 mg, 0.5 mmol) and bis (2-methoxyethyl) ether were prepared. (5 ml) of the solution was stirred at reflux for 5 hours. After cooling, it was evaporated under reduced pressure. The residue was purified by column chromatography using hexane: ethyl acetate (3 4: 6 6) as the eluent on silica gel to obtain the title compound (520 mg) as a solid. Elemental analysis: 値: C, 6 1 · 40; Η, 5 · 8 6; N, 20 · 28. C21H24n6〇3 calculates 値 C, 61 · 75; This paper size is applicable to China National Standard (CNS) A4 specification (21 〇χ 297 公 楚) _ 253-(Please read the precautions on the back before filling this page) Order Φ Printed by the Consumer Cooperatives of the Central Standards Bureau of the Ministry of Economic Affairs 524805 A7 B7 V. Description of Invention (251) Η, 5.92; N, 20.57%. (5 (DMS 0 d 6): 0.95 (6H, m), 1 · 7 4 (4 Η, m), 2 · 5 8 (3 Η, s), 2 · 9 8 (2 Η, t) , 4 · 〇3 (2 Η, t), 5 · 7 6 (2 Η, s), 7 · 〇 6 (1 Η, m), 7 · 16 (1 Η, d), 7 · 4 5 ( 1 Η, m), 7 · 6 6 (1 Η, d), 11.55 (lH, s) ° LRMS: m / z 4〇9 (M + 1) +. Preparation Example 7 7 2 —Cyanomethyl-5 — (2 —Ethoxyphenyl) — 3 —n-propyl — 2,6 —dihydro — 7H — pyrazolo [4,3 — d] pyrimidin — 7 —one From the title compound of Preparation 14 and bromine Acetonitrile was prepared according to the procedure of Preparation 73, and it was solid (73%). 5 (CDC 1 a): 1, 10 (3H, t), 1.6 〇 (3 Η, t), 1. 9 5 (2 Η, m), 3 · 0 8 (2 Η, t), this paper size applies Chinese National Standard (CNS) Α4 specification (210X297 mm) ~-254-~ (Read the precautions on the back before reading (Fill in this page)

524805 A7 B7 五、發明説明（252) 4 · 3 1 ( 2 Η，q )， 5 . 2 8 ( 2 Η，s )， 7 ·〇 7 ( 1 Η，d )， 7 · 1 4 ( 1 Η，m )， 7 · 4 8 ( 1 Η，m )， 8 · 4 2 ( 1 Η，d )， 11.01(lH，s)。 L R M S ： m / z 338 (M+1)+。 製備例7 8 2 —〔5— (2 —乙氧苯基）—3 —正丙基—2，6 —二氫—7H —吡唑並〔4，3 - d〕嘧啶—7 —酮—2 —基〕acetamidoxime 由製備例7 7之標題化合物依製備例7 4之步驟製得 ，呈白色固體（89%)。 5 ( D M S 0 d 6 ):〇·94(3Η，ΐ)， 1 · 3 3 ( 3 Η，t )， 1 · 7 4 ( 2 Η，m )， 2 · 9 0 ( 2 Η，t )， 4 . 12 ( 2 Η > q )， 4 · 9 2 ( 2 Η，s )， 5.48(2H，s)， 7 · 0 7 ( 1 Η，m )， 7 . 1 4 ( 1 Η，d )， 本紙張尺度適用中國國家標準（CNS ) Α4規格（210X29*7公釐）-255 - (請先閱讀背面之注意事項再填寫本頁524805 A7 B7 V. Description of the invention (252) 4 · 3 1 (2 Η, q), 5. 2 8 (2 Η, s), 7 · 07 (1 Η, d), 7 · 1 4 (1 Η , M), 7 · 4 8 (1 Η, m), 8 · 4 2 (1 Η, d), 11.01 (lH, s). L R M S: m / z 338 (M + 1) +. Preparation Example 7 8 2 — [5 -— (2-ethoxyphenyl) -3—n-propyl-2,6-dihydro-7H—pyrazolo [4,3-d] pyrimidin-7-one-2 —Base] acetamidoxime was prepared from the title compound of Preparation Example 7 7 according to the procedure of Preparation Example 74, as a white solid (89%). 5 (DMS 0 d 6): 0.94 (3Η, ΐ), 1 · 3 3 (3 Η, t), 1 · 7 4 (2 Η, m), 2 · 9 0 (2 Η, t), 4. 12 (2 Η > q), 4 · 9 2 (2 Η, s), 5.48 (2H, s), 7 · 0 7 (1 Η, m), 7. 1 4 (1 Η, d) ， This paper size is applicable to Chinese National Standard (CNS) Α4 specification (210X29 * 7mm) -255-(Please read the precautions on the back before filling this page

、1T 經濟部中央標準局員工消費合作社印製 524805 A7 B7 五、發明説明（253) 7.46 (lH，m)， 7 · 6 8 ( 1 Η，d )， 9 · 3 4 ( 1 Η，s )， 11.53(lH，s)° LRMS:m/z 371 (M+l)+。 製備例7 g 5— (2 —乙氧苯基）一2— (5 —甲基一1 ，2， 4 — d琴一 d坐一 3 一基）甲基一 3 一正丙基—2，6 —二氫 —7 Η —吡唑並〔4，3 — d〕嘧啶—7 —酮 將製備例7 8之標題化合物（1 6 0 m g，0 · 4 3 mmo 1)加入含有乙酸酐（122//1 ，1 · 3 mmol)，乙酸（2 · 5 ml ，4〇mmo 1)及甲苯 (2 m 1 )的混合物裡，再將整個混合物攪拌迴流1 8小 時，經冷卻後減壓蒸發。殘餘物以管柱層析法利用己烷： 乙酸乙酯（1 : 1至1 : 3 )之沖提梯度於矽膠上純化而 經濟部中央標準局員工消費合作社印製Printed by the Consumer Cooperative of the Central Standards Bureau of the Ministry of Economic Affairs, 1T 524805 A7 B7 V. Description of the invention (253) 7.46 (lH, m), 7 · 6 8 (1 Η, d), 9 · 3 4 (1 Η, s) , 11.53 (lH, s) ° LRMS: m / z 371 (M + l) +. Preparation Example 7 g 5— (2-ethoxyphenyl) —2— (5-methyl-1, 2, 4—d, phenyl, d, —3—yl) —methyl—3—n-propyl-2, 6-Dihydro-7 pyrene-pyrazolo [4,3 — d] pyrimidin-7-one The title compound of Preparation Example 7 (160 mg, 0.43 mmo 1) was added to acetic anhydride (122 // 1, 1.3 mmol), acetic acid (2.5 ml, 40 mmo 1) and toluene (2 m 1), and the whole mixture was stirred at reflux for 18 hours. After cooling, it was evaporated under reduced pressure. The residue was purified by column chromatography using a gradient of hexane: ethyl acetate (1: 1 to 1: 3) on silica gel and printed by the Consumer Cooperative of the Central Standards Bureau of the Ministry of Economic Affairs.

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Q s (請先閱讀背面之注意事項再填寫本頁)Q s (Please read the notes on the back before filling this page)

本紙張尺度適用中國國家標準（CNS ) A4規格（210X 297公釐）-256 - 524805 A7 B7 經濟部中央標準局員工消費合作社印製 五、發明説明（254)7.〇5(lH，m)， 7 · 1 4 ( 1 Η，d )， 7 · 4 7 ( 1 Η，m )， 7 · 6 4 ( 1 Η，d )， 1 1 · 6 4 ( 1 Η，s )。 製備例8 0 1 一苄基一 4 一硝基一 3 -正丙基吡唑一 5 -羧酸苄 酯 在5分鐘時間內將苄基溴（2 0 · 4 m 1 ， 0 · 1 7 2 m ο 1 )逐滴加入一攪拌中且以冰冷卻而含有 製備例3標題化合物（1 7 · 0 g，0 · 0 8 5 m ο 1 ) 與碳酸鉋（56 · lg ，〇· 173mo 1)於二甲基甲 醯胺（1 5 0 m 1 )中所形成的溶液裡，然後把冷卻浴移 開。1 9小時後加水（3 0 0 m 1 )，再以乙醚（總量1 0 0 0 m 1 )對該混合物進行萃取。萃取液合倂後乾燥（ M g S 0 4 )並減壓蒸發而得油狀物，以管柱層析法戊烷： 乙酸乙酯（9 5 ·· 5至9 0 0 ·· 1 0 )之沖提梯度於矽膠 上純化該油狀物而得到固態標題化合物（1 3 · 0 g )( 及其2 -苄基異構物19. 7g)。 5(CDCl3):〇.99(3H，t)， 1 · 7 6 ( 2 Η，m )，2.86(2H，t)， 5 · 3 0 ( 2 Η，s )， 本紙張尺度適用中國國家標準（CNS ) Α4規枱（210Χ 297公釐）-257 - (讀先閱讀背面之注意事項再填寫本百〇This paper size applies to China National Standard (CNS) A4 (210X 297 mm) -256-524805 A7 B7 Printed by the Consumer Cooperatives of the Central Standards Bureau of the Ministry of Economic Affairs 5. Description of the invention (254) 7.05 (lH, m) , 7 · 1 4 (1 Η, d), 7 · 4 7 (1 Η, m), 7 · 6 4 (1 Η, d), 1 1 · 6 4 (1 Η, s). Preparation Example 8 0 1-Benzyl- 4 -Nitro- 3 -n-propylpyrazole-5 -carboxylic acid benzyl ester. Benzyl bromide (2 0 · 4 m 1, 0 · 1 7 2 m ο 1) was added dropwise to a stirring and ice-cooled to contain the title compound of Preparation Example 3 (17 · 0 g, 0 · 0 8 5 m ο 1) and carbonic acid planer (56 · lg, · 173mo 1) In a solution formed in dimethylformamide (150 m 1), the cooling bath was removed. After 19 hours, water (300 m 1) was added, and the mixture was extracted with diethyl ether (a total of 100 m 1). The extract was combined and dried (M g S 0 4) and evaporated under reduced pressure to give an oil. The column was pentane: ethyl acetate (9 5 ·· 5 to 9 0 0 ·· 1 0) The gradient was purified on silica gel to give the title compound (13.0 g) (and its 2-benzyl isomer 19.7 g) as a solid. 5 (CDCl3): 0.99 (3H, t), 1.76 (2 Η, m), 2.86 (2H, t), 5.30 (2 Η, s), this paper size applies Chinese national standards (CNS) Α4 gauge (210 × 297 mm) -257-(Read the precautions on the back before filling this one hundred.

、1T * 524805 經濟部中央標準局員工消費合作社印製 A7 B7 五、發明説明（255) 5 · 3 9 ( 2 Η，s )， 7 · 1 7 ( 2 Η，m )， 7.30(8H，m)，。 L R M S ： m / z 397 (M+18)+。 製備例8 1 1 —苄基—4 一硝基—3 —正丙基吡唑一 5 —羧酸 將製備例8 0之標題化合物（1 3 . 0 g， 0 · 0 3 4mo 1 )與6M氫氧化鈉水溶液（6 5m 1 ) 之混合物攪拌迴流2小時，冷卻後以水（1 3 0 m 1 )稀 釋，再用乙醚（5 0 0 m 1 )萃取。水相部份以冰冷卻， 用濃氫氯酸加以酸化，再以二氯甲烷（總量5 0 0 m 1 ) 萃取。二氯甲烷萃取液合倂後乾燥（M g S〇4 )並減壓蒸 發而得白色固體標題化合物（10. Og)。 5(CDCl3):1.10(3H，t)， 1 · 7 8 ( 2 Η，m )， 2 · 9 4 ( 2 Η，t )， 5 · 7 8 ( 2 Η，s )， 7 · 3 2 ( 5 Η，m )。 製備例8 2 1 一苄基一 4 一硝基一 3 —正丙基吡唑一 5 —甲醯胺 由製備例8 1之標題化合物依製備例5之步驟製彳辱’ 呈乳粉末（creampowder) (79%)。 本紙張尺度適用中國國家標準（CNS ) Α4規枱（210X 297公釐）-258 - (請先閲讀背面之注意事項再填寫本頁 一裝·1T * 524805 Printed by the Consumer Cooperatives of the Central Standards Bureau of the Ministry of Economic Affairs A7 B7 V. Description of the invention (255) 5 · 3 9 (2 Η, s), 7 · 1 7 (2 Η, m), 7.30 (8H, m ). L R M S: m / z 397 (M + 18) +. Preparation Example 8 1 1 -Benzyl-4 -nitro-3 -n-propylpyrazole-5 -carboxylic acid The title compound of Preparation 80 (1 3.0 g, 0 · 0 3 4mo 1) and 6M A mixture of an aqueous sodium hydroxide solution (6.5 m 1) was stirred under reflux for 2 hours. After cooling, it was diluted with water (130 m 1) and extracted with ether (500 m 1). The aqueous phase was cooled with ice, acidified with concentrated hydrochloric acid, and extracted with dichloromethane (total 500 m 1). Og). The dichloromethane extract was combined and dried (Mg S04) and evaporated under reduced pressure to give the title compound (10.0 g) as a white solid. 5 (CDCl3): 1.10 (3H, t), 1 · 7 8 (2 Η, m), 2 · 9 4 (2 Η, t), 5 · 7 8 (2 Η, s), 7 · 3 2 ( 5 Η, m). Preparation 8 2 1 -Benzyl-4 -Nitro-3 -n-propylpyrazole 5 -formamidine Prepared from the title compound of Preparation 8 1 according to the procedure of Preparation 5 'Cream powder (creampowder ) (79%). This paper size applies Chinese National Standard (CNS) Α4 gauge (210X 297 mm) -258-(Please read the precautions on the back before filling this page

、1T 524805 A7 ΒΊ 五、發明説明（256) 5 ( C D C 1 3 ) :1.0〇（3H，t)， 1.76(2H，m)’ 2 · 9 〇（2 Η，t )， 5 · 6 Ο ( 2 Η，s )， 7 · 3 〇（5 Η，m )。 L R Μ S ： m / z 3〇6(M+18)+。 製備例8 3 4 一胺基—1 一苄基一 3 -正丙基吡唑一 5 —甲醯胺 將製備例82標題化合物（7 · Og，0 · 024 mol)，氯化錫（Π )二水合物（2 7 · 4 g， 0 · 1 2 2 m ο 1 )與乙醇（1 4 0 m 1 )之混合物加熱 迴流2小時，冷卻後用飽和碳酸銨水溶液鹼化，經過濾後 其濾液以二氯甲烷（總量7 5 0 m 1 )萃取。把萃取液合 倂並乾燥（M g S〇4 )，再減壓蒸發而得到呈橙色固體之 標題化合物（4 · 8 g )。 5 ( C D C 1 3 ):〇.99(3H，t)， 1 · 7 〇（2 Η，m )， 經濟部中央標準局員工消費合作社印製 |裝I (請先閱讀背面之注意事項再填寫本頁 、11 Φ 2.58(2H，t)， 2 · 9 4 ( 2 Η，s )， 5 · 7 0 ( 2 Η，s )， 7 · 2 4 ( 5 Η，m )。 LRMS:m/z 259(Μ+1)+〇 本紙張尺度適用中國國家標準（CNS ) A4規枱（210X297公釐）_ 259 _ 524805 經濟部中央標準局員工消費合作社印製 A7 B7 五、發明説明（25乃 製備例8 4 5 —氯磺醯基一 2 —乙氧苄酸 把熔融的2 —乙氧苄酸（2 5 ·〇g ，〇·工5 0 m 〇 1 )加入一攪拌中且以冰冷卻而含有硫醯氯（丄工 ml ，0·151τηο1)與氯磺酸（4ι·3ιη1 ， 0 · 6 2 1 m ο 1 )的混合物裡，同時維持溫度低於2 5 °C。令所得混合物於室溫下攪拌1 8小時，然後倒入含有 冰（2 7 0 g )和水（6 0 m 1 )的攪拌混合物裡而得灰 色沈澱物。持續攪拌1小時，以過濾方式收集產物，用水 洗過，真空乾燥而得標題化合物（3 6 8 g )。以己 烷：甲苯進行結晶而得參考試樣，m · ρ · 1 1 5 — 1 1 6 t：。 元素分析實測値：C，4 1 · 〇 2 ; Η，3 · 2 7。 C9H9C1〇5S 計算値 c，4〇 · 84 ;Η，3 · 43 %。 5(CDC13) :1.64(3H，t)， 4.45(2H，q)， 7-26(lH,d)， 8.20(lH，dd)， 8 · 8 0 ( 1 h，d )。 製備例8 5 2 一乙氧〜5 — (4 -甲基六氫吡畊—1 一基磺醯基 )苄酸 (讀先閱讀背面之注意事項再填寫本頁)1T 524805 A7 BΊ V. Description of the invention (256) 5 (CDC 1 3): 1.00 (3H, t), 1.76 (2H, m) '2 · 9 〇 (2Η, t), 5 · 6 Ο ( 2 Η, s), 7 · 3 〇 (5 Η, m). L R M S: m / z 306 (M + 18) +. Preparation Example 8 3 4 Monoamino-1, 1-benzyl-3, n-propylpyrazole, 5-formamidine The title compound of Preparation 82 (7 · Og, 0 · 024 mol), and tin chloride (Π) A mixture of dihydrate (27 · 4 g, 0 · 1 2 2 m ο 1) and ethanol (14 0 m 1) was heated under reflux for 2 hours, and after cooling, it was basified with a saturated ammonium carbonate aqueous solution, and the filtrate was filtered. Extract with dichloromethane (total 750 m 1). The extract was combined and dried (MgS04), and evaporated under reduced pressure to give the title compound (4.8 g) as an orange solid. 5 (CDC 1 3): 0.99 (3H, t), 1 · 7 〇 (2 Η, m), printed by the Consumer Cooperatives of the Central Standards Bureau of the Ministry of Economic Affairs | Equipment I (Please read the precautions on the back before filling This page, 11 Φ 2.58 (2H, t), 2 · 9 4 (2 Η, s), 5 · 7 0 (2 Η, s), 7 · 2 4 (5 Η, m). LRMS: m / z 259 (Μ + 1) + 〇 This paper size applies Chinese National Standard (CNS) A4 gauge (210X297 mm) _ 259 _ 524805 Printed by A7, B7, Consumer Cooperative of the Central Standards Bureau of the Ministry of Economic Affairs. Example 8 4 5 -Chlorosulfonyl-2-ethoxybenzyl acid Molten 2-ethoxybenzyl acid (25.0 g, 0.5 g 50 m 〇1) was added to a stirring and cooled with ice to In a mixture containing thiosulfuric chloride (machinary ml, 0.151τηο1) and chlorosulfonic acid (4ι · 3ιη1, 0 · 6 2 1 m ο 1), while maintaining the temperature below 25 ° C. Let the resulting mixture in a chamber Stir at room temperature for 18 hours, then pour into a stirred mixture containing ice (270 g) and water (60 m 1) to obtain a gray precipitate. Continue stirring for 1 hour, collect the product by filtration, and wash with water , Vacuum drying and The title compound (3 6 8 g). Crystallized from hexane: toluene to obtain a reference sample, m · ρ · 1 1 5 — 1 1 6 t :. Elemental analysis found 値: C, 4 1 · 〇2; Η , 3 · 2 7. C9H9C1O5S calculates 値 c, 40 · 84; Η, 3.43%. 5 (CDC13): 1.64 (3H, t), 4.45 (2H, q), 7-26 (lH, d), 8.20 (lH, dd), 8.80 (1 h, d). Preparation Example 8 5 2 Ethoxy ~ 5 — (4-methylhexahydropyridine-1 monosulfosulfanyl) benzyl Acid (read the precautions on the back before filling this page)

本紙張-尺度適用中關家標準（CNS ) M規格（MX29?公楚） -260- 524805 經濟部中央標準局員工消費合作社印製 A7 B7 五、發明説明（258) (a )單一步驟法 在約1 0 t下將1 —甲基六氫吡哄（3 3 · 6 m 1 ， 〇 · 3〇3m〇 1)加入一攪拌中含有製備例84標題化 口物（34 · 4g ，〇.13〇m〇1)與水（124 m 1 )之懸浮液裡，同時維持反應混合物的溫度低於2 0 °C °把所得溶液冷卻到大約1 〇，5分鐘後開始有固體 結晶化。再2小時後，過濾收集固體，以冰-水洗過，再 真空乾燥而得粗產物（3 6 · 7 g )。取一些試樣（ 1 5 · 〇 g )加以純化，純化方式係令其於迴流的丙酮中 S拌1小時，令所得懸浮液冷卻至室溫，然後過濾收集結 晶固體，經真空乾燥而得標題化合物（1 1 . 7 g )。 m· P · 198 — 199 t，其1 H nmr光譜與由以下 步驟（b )產物所得光譜相同。 (b )二步驟法 將製備例8 4標題化合物（5 0 · 0 g，〇· 1 8 9 m 〇 1 )於丙酮（1 5 0 m 1 )中所形成的溶液逐滴加入 一攪拌中而含有1—甲基六氫吡畊（20 · 81g， 〇.2〇8111〇1)與三乙胺（28.91111， 0 · 2 0 7 m ο 1 )的混合物裡，同時維持反應混合物的 溫度低於2 0 °C。在添加期間會有白色晶狀固體生成，持 續攪拌1 · 5小時。經過濾，以丙酮洗之，然後真空乾燥 產物而得到標題化合物的氯化氫-三乙胺複鹽（7 8 · 9 7 g ) ° 本紙張尺度適用中國國家標準（CNS ) Α4規格（210Χ 297公釐）-261 - (請先閱讀背面之注意事項再填寫本頁)This paper-size applies the Zhongguanjia Standard (CNS) M specification (MX29? Gongchu) -260- 524805 Printed by the Consumers' Cooperative of the Central Standards Bureau of the Ministry of Economic Affairs A7 B7 V. Description of the invention (258) (a) The single-step method is At about 10 t, 1-methylhexahydropyridine (33.6 m1, 0.30 m3) was added to the mixture with stirring and contained the title compound of Preparation Example 84 (34.4 g, 0.13 〇m〇1) and water (124 m 1) in a suspension, while maintaining the temperature of the reaction mixture below 20 ° C ° to cool the resulting solution to about 10, 5 minutes after the start of solid crystallization. After another 2 hours, the solid was collected by filtration, washed with ice-water, and dried under vacuum to obtain a crude product (36 · 7 g). Take some samples (15 · 0 g) for purification. The purification method is to stir them in refluxing acetone for 1 hour, allow the resulting suspension to cool to room temperature, then collect the crystalline solid by filtration, and dry under vacuum to obtain the title. Compound (11.7 g). m · P · 198-199 t, the 1 H nmr spectrum is the same as that obtained from the product of step (b) below. (b) a two-step method, adding the solution of the title compound of Preparation Example 84 (50 · 0 g, 0. 189 m 〇1) in acetone (150 m 1) dropwise into a stirring solution, and In a mixture containing 1-methylhexahydropyridine (20.81g, 0.2081111) and triethylamine (28.91111, 0. 2 0 7 m ο 1), while maintaining the temperature of the reaction mixture below 2 0 ° C. During the addition, a white crystalline solid was formed, and stirring was continued for 1.5 hours. After filtration, washing with acetone, and then drying the product in vacuo to obtain the title compound of hydrogen chloride-triethylamine double salt (7 8 · 9 7 g) ° This paper size applies to China National Standard (CNS) A4 size (210 × 297 mm) ) -261-(Please read the notes on the back before filling this page)

、1T 524805 經濟部中央標準局員工消費合作社印製 A7 B7 --~ 五、發明説明（259) m · P · 1 6 6 — 1 6 9 °C。元素分析實測値：C， 5l.33;H，8.14;N，9.06;Cl， 8 · 02 · C14H20N2O5S ; C6H15N ; HC 1 言十 算値C，51.55;H，7.79;N，9.02; c 1，7 · 6 1 %。 5(DMS〇d6):1.17(9H，t)， 1 · 3 2 ( 3 Η，t )， 2. 15 (3Hj s)， 2.47(6H，br s)， 2.86(2H，br s )， 3 ·〇 2 ( 6 H，q )， 4 · 1 8 ( 2 H，q )， 7 · 3 2 ( 1 H，d )， 7.78(lH，dd)， 7.85(lH，d)。 將該複鹽（30 · Og)置於水（120ml)中攪 祥而形成幾乎澄淸的溶液，固體結晶很快地自此溶液產生 ° 2小時之後過濾收集該固體，以水洗之，再真空乾燥而 #到呈白色固體之標題化合物（1 4 · 6 1 g)。以乙醇 水溶液（aqueous ethanol )再結晶而得到參考試樣。 m · P · 2 0 1 °C，元素分析實測値：C，5 1 · 〇 9 ; Η 6 · 16 ’Ν’ 8 · 43。Ci4H2〇N2〇5S 巨十算 値〇’51·21;Η，6·14;Ν，8·53%。 占（DMS〇d6):i.31(3H，t)， I紙張尺度適财關家標準（CNS ) A4職（21()><297公楚）~「262 - '〜-- (請先閱讀背面之注意事項再填寫本頁)1T 524805 Printed by the Consumer Cooperatives of the Central Standards Bureau of the Ministry of Economic Affairs A7 B7-~ V. Description of the invention (259) m · P · 1 6 6-1 6 9 ° C. Elemental analysis: 値: C, 5l.33; H, 8.14; N, 9.06; Cl, 8 · 02 · C14H20N2O5S; C6H15N; HC 1 十 値 C, 51.55; H, 7.79; N, 9.02; c 1, 7 · 6 1%. 5 (DMS〇d6): 1.17 (9H, t), 1.3.2 (3H, t), 2.15 (3Hj s), 2.47 (6H, br s), 2.86 (2H, br s), 3 • 〇2 (6H, q), 4 · 18 (2H, q), 7 · 32 (1H, d), 7.78 (lH, dd), 7.85 (lH, d). The double salt (30 · Og) was stirred in water (120ml) to form an almost clear solution. Solid crystals quickly formed from this solution. After 2 hours, the solid was collected by filtration, washed with water, and then vacuumed. The title compound was dried to a white solid (14.61 g). A reference ethanol was obtained by recrystallization from an aqueous ethanol solution. m · P · 2 01 ° C, measured by elemental analysis C: C, 5 1 · 〇 9; Η 6 · 16 'N' 8 · 43. Ci4H2〇N2〇5S giant ten count 値 〇′51 · 21; Η, 6.14; N, 8.53%. Account (DMS〇d6): i.31 (3H, t), I Paper Standards Financial Standards (CNS) A4 position (21 () > < 297 Gongchu) ~ "262-'~-( (Please read the notes on the back before filling out this page)

524805 經濟部中央標準局員工消費合作社印製524805 Printed by the Consumer Cooperative of the Central Bureau of Standards of the Ministry of Economic Affairs

A7 B7 五、發明説明（26〇) 2 · 1 2 ( 3 Η，s )， 2.34(4H，br s )， 2.84(4H，br s )， 4 · 2 〇（2 H，q )， 7 · 3 2 ( 1 H，d )， 7.8〇（lH，dd)， 7 · 8 6 ( 1 H，d )。 製備例8 6 1—卡基一4 —〔2 —乙氧一 5 —（4 —甲基六氣批 哄一 1 一基磺醯基）苄醯胺基〕一 3 -正丙基吡唑一 5 — 甲醯胺 將六氟磷酸（苯並三唑一 1 一基氧）三吡略啶銹（ PyB〇P ; 7 · 6g ，〇· 〇l5m〇1)加入製備例 83標題化合物（3 · 8g，〇 .〇15mo 1)和製備 例85標題化合物（5 · 3g，〇 · 016mo 1)在二 甲基甲醯胺（5 Om 1 )中所形成的攪拌溶液裡。令所得 橙色溶液於室溫下攪拌2 0小時，然後倒入水（2 5〇 m 1 )裡。以乙酸乙酯（總量7 5 0 m 1 )對該混合物進 行萃取，合倂的萃取液依續以1 〇 %碳酸氫鈉水溶液（ 1〇0 m 1 )及水（1 〇 〇 m 1 )洗過，經乾燥（ M g S 0 4 )並減壓蒸發而得橙色固體。以乙醇進行結晶而 得白色晶狀固體之標題化合物。 m · ρ · 1 8 2 — 1 8 4 °C。元素分析實測値：c， 本纸張尺度適用中國國家標準（CNS ) A4規格（210X29h>i~7^263 - " (請先閱讀背面之注意事項再填寫本頁)A7 B7 V. Description of the invention (26〇) 2 · 1 2 (3 Η, s), 2.34 (4H, br s), 2.84 (4H, br s), 4 · 2 〇 (2 H, q), 7 · 3 2 (1 H, d), 7.8 (1 H, dd), 7.8 (1 H, d). Preparation Example 8 6 1-Carbonyl-4— [2-Ethoxy-5— (4-methylhexazine) —1-Sulfosulfenylbenzylamido]] 3-N-propylpyrazole— 5- Formamidine Added hexafluorophosphate (benzotriazole-1 monooxy) tripyridoxine (PyBOP; 7.6 g, 〇.15m〇1) to the title compound of Preparation 83 (3. 8 g, 0.015 mo 1) and a stirring solution of the title compound of Preparation Example 85 (5.3 g, 0.016 mo 1) in dimethylformamide (50 m 1). The resulting orange solution was allowed to stir at room temperature for 20 hours, and then poured into water (250 m 1). The mixture was extracted with ethyl acetate (total 750 m 1), and the combined extracts were successively 10% aqueous sodium hydrogen carbonate solution (100 m 1) and water (100 m 1). It was washed, dried (MgSO4) and evaporated under reduced pressure to give an orange solid. Crystallization from ethanol gave the title compound as a white crystalline solid. m · ρ · 1 8 2 — 1 8 4 ° C. Elemental analysis: 値, c, this paper size is applicable to China National Standard (CNS) A4 specification (210X29h > i ~ 7 ^ 263-" (Please read the precautions on the back before filling this page)

524805 A7 B7 經濟部中央標準局員工消費合作社印製 五、發明説明（261) 58.88 ·’ Η，6·27;Ν，14,66。 C28H36N6〇5S 計算値 C，59 · 14 ; Η， 6·38;Ν，14.78%。 δ ( C D C 1 a ):〇.97(3H，t)， 1 · 5 9 ( 3 Η，t )， 1 · 6 8 ( 2 Η，m )， 2 · 2 6 ( 3 Η，s )， 2 · 4 7 ( 4 Η，m )， 2 · 5 8 ( 2 Η，t )， 3 ·〇 8 ( 4 Η，m )， 4 · 3 9 ( 2 Η，t )， 5 · 6 2 ( 2 Η，s )， 7 · 1 7 ( 1 Η，d )， 7 · 2 6 ( 7 Η，m )， 7 · 9 2 ( 1 Η，d )， 8 · 6 2 ( 1 Η，s )， 9 · 2 Ο ( 1 Η，s )。 L R Μ S ： m / ζ 569 (M+1)+。 製備例8 7 1 一（4 一氯苄基）—5 -（2 -正丙氧苯基）一 3 一正丙基—1，6 —二氫—7H -吡唑並〔4，3 — d〕 嘧η定一 7 -酮 由製備例1 2標題化合物及4 -氯苄基氯依製備例 (請先閲讀背面之注意事項再填寫本頁)524805 A7 B7 Printed by the Consumer Cooperatives of the Central Bureau of Standards of the Ministry of Economic Affairs. 5. Description of the invention (261) 58.88 · ’Η, 6.27; N, 14,66. C28H36N6〇5S calculated 値 C, 59 · 14; Η, 6.38; N, 14.78%. δ (CDC 1 a): 0.97 (3H, t), 1 · 5 9 (3 Η, t), 1 · 6 8 (2 Η, m), 2 · 2 6 (3 Η, s), 2 · 4 7 (4 Η, m), 2 · 5 8 (2 Η, t), 3 · 〇8 (4 Η, m), 4 · 3 9 (2 Η, t), 5 · 6 2 (2 Η , S), 7 · 1 7 (1 Η, d), 7 · 2 6 (7 Η, m), 7 · 9 2 (1 Η, d), 8 · 6 2 (1 Η, s), 9 · 2 Ο (1 Η, s). L R M S: m / ζ 569 (M + 1) +. Preparation Example 8 7 1 mono (4-chlorobenzyl) -5-(2-n-propoxyphenyl) -3 mono-n-propyl-1,6-dihydro-7H-pyrazolo [4,3 — d ] Pyrimidine a 7-one prepared from the title compound of Preparation Example 12 and 4-chlorobenzylchloride (please read the precautions on the back before filling in this page)

裝· Φ 本紙張尺度適用中國國家標準（CNS ) A4規輅（210X 297公釐）-264 - 524805 A7 經濟部中央標準局員工消費合作社印製 B7 五、發明説明（262) 15A之步驟製得，呈白色固體（62%)。 元素分析實測値：C，6 5 · 9 6 ; Η，5 · 8〇；N， 12 · 77。C24H25C 1Ν4〇2 計算値 C， 65·9 7;Η，5·77;Ν，12·82%。 5(CDCl3):l.〇2(3H，t)， 1 · 1 8 ( 3 Η，t )， 1 · 8 8 ( 2 Η，m )， 2 ·〇 2 ( 2 Η，m )， 2 · 9 5 ( 2 Η，t )， 4 · 1 9 ( 2 Η，t )， 5 · 7 4 ( 2 Η，s )， 7 ·〇 4 ( 1 Η，d )， 7 · 1 6 ( 1 Η，m )， 7 · 2 6 ( 2 Η，d )， 7 · 3 7 ( 2 Η，d )， 7 · 4 4 ( 1 Η，m )， 8 · 5 〇（1 Η，d )， 11.20(lH，s)。 L R M S ： m / z 437 (M+1)+。 製備例8 8 1— (4 —氯爷基）—5 — (2 —乙氧苯基）一3 — 正丙基—1，6 -二氫—7H -吡唑並〔4，3 — d〕嘧 D定一 7 —醒 (請先閲讀背面之注意事項再填寫本頁)Packing · Φ This paper size is in accordance with Chinese National Standard (CNS) A4 (210X 297 mm) -264-524805 A7 Printed by the Consumer Cooperatives of the Central Standards Bureau of the Ministry of Economic Affairs, printed by B7 V. Invention (262) 15A As a white solid (62%). Elemental analysis: 値: C, 6 5 · 9 6; Η, 5 · 80; N, 12 · 77. C24H25C 1N4〇2 Calculate 値 C, 65 · 9 7; Η, 5.77; Ν, 12.82%. 5 (CDCl3): 1.02 (3H, t), 1 · 1 8 (3 Η, t), 1 · 8 8 (2 Η, m), 2 · 〇 2 (2 Η, m), 2 · 9 5 (2 Η, t), 4 · 1 9 (2 Η, t), 5 · 7 4 (2 Η, s), 7 · 〇 4 (1 Η, d), 7 · 1 6 (1 Η, m), 7 · 2 6 (2 Η, d), 7 · 3 7 (2 Η, d), 7 · 4 4 (1 Η, m), 8 · 5 〇 (1 Η, d), 11.20 (lH , S). L R M S: m / z 437 (M + 1) +. Preparation Example 8 8 1— (4-Chloroyl) -5— (2-Ethoxyphenyl) —3—n-propyl-1,6-dihydro-7H-pyrazolo [4,3 — d] Pyridine Ding 7-wake up (please read the precautions on the back before filling this page)

裝. "口 本纸張尺度適用中國國家標準（CNS ) A4規格（210Χ 297公釐）-265 - 經濟部中央標準局員工消費合作社印製 524805 A7 B7 五、發明説明（263) 由製備例14之標題化合物及4-氯苄基氯依製備例 1 5 A之步驟製得，呈白色晶狀固體（7 7 % )。 元素分析實測値：C，6 5 . 3 4 ; Η，5 · 5 2 ; N， 13 · 38。C23H23C 1Ν4〇2 計算値 C， 65·32;Η，5·48 ;Ν，13.25%。 5(CDCl3):l.〇2(3H，t)， 1 · 6 3 ( 3 Η，t )， 1 · 9 〇（2 Η，m )， 2 · 9 6 ( 2 Η，t )， 4 · 3 2 ( 2 Η，q )， 5 · 7 4 ( 2 Η，s )， 7 ·〇 5 ( 1 Η，d )， 7 · 1 6 ( 1 Η，m )， 7 · 2 8 ( 2 Η，d )， 7 · 3 8 ( 2 Η，d )， 7 · 4 6 ( 1 Η，m )， 8 · 5 Ο ( 1 Η，d )， 11.2〇（lH，s)° L R M S ： m / z 423 (M+1)+。 製備例8 9 2 — (4 —溴苄基）—5 —（2 —乙氧苯基）—3 — 正丙基—1，6 —二氫一 7H —吡唑並〔4，3 — d〕嘧 啶—7 —酮 (請先閱讀背面之注意事項再填寫本頁)&Quot; The size of the paper is applicable to the Chinese National Standard (CNS) A4 (210 × 297 mm) -265-printed by the Consumer Cooperatives of the Central Bureau of Standards of the Ministry of Economic Affairs 524805 A7 B7 V. Description of the invention (263) By the preparation The title compound of 14 and 4-chlorobenzyl chloride were prepared according to the procedure in Preparation Example 15A, and showed a white crystalline solid (77%). Elemental analysis: 値: C, 6 5. 3 4; Η, 5 · 5 2; N, 13 · 38. C23H23C 1N4O2 Calculate 値 C, 65 · 32; Η, 5.48; Ν, 13.25%. 5 (CDCl3): 1.02 (3H, t), 1.63 (3 Η, t), 1 · 9 〇 (2 Η, m), 2 · 96 (2 Η, t), 4 · 3 2 (2 Η, q), 5 · 7 4 (2 Η, s), 7 · 〇5 (1 Η, d), 7 · 1 6 (1 Η, m), 7 · 2 8 (2 Η, d), 7 · 3 8 (2 Η, d), 7 · 4 6 (1 Η, m), 8 · 5 〇 (1 Η, d), 11.2〇 (lH, s) ° LRMS: m / z 423 (M + 1) +. Production Example 8 9 2 — (4-Bromobenzyl) — 5 — (2-ethoxyphenyl) — 3 —n-propyl-1,6 —dihydro-7H —pyrazolo [4,3 — d] Pyrimidine-7-one (Please read the precautions on the back before filling this page)

、1T - 本纸張尺度適用中國國家標準（CNS ) A4規枱（210X 297公釐）-266 - 524805 A7 B7 五、發明説明（264) 由製備例1 4之標題化合物及4 -溴苄基氯依製備例 1 5 B之步驟製得，呈黃色油狀物（5 4 % )。 5 ( C D C 1 3 ):〇.94(3H，t)， 1 · 5 8 ( 3 Η，t )， 1 · 7 3 ( 2 Η，m )， 2 . Ο 8 ( 2 Η，t )， 4 ·〇 8 ( 2 Η，q )， 5 · 5 Ο ( 2 Η，s )， 7 · Ο 8 ( 4 Η，m )， 7 · 4 4 ( 3 Η，m )， 8.38(lH，d)， 10.89(lH，s)° L R Μ S ： m / z 484 (M+18)+。 製備例9 0 1一（2 —氰；基）一5 —（2 —乙氧苯基）一3 — 正丙基—1，6 -二氫—7H —吼卩坐並〔4，3 — d〕嘧 啶一 7 -酮 由製備例1 4之標題化合物及2 -氰苄基溴依製備例 15D之步驟製得，呈固體（17%)。 兀素分析實測値：C，69 · 58 ;H，5 · 60 ;N， 1 6 · 9 0 。C24H23N5〇2計算値 C ，69 · 72 ； Η，5·61;Ν，16.94%。 5(CDCl3):l.〇3(3H，t)， 本紙張尺度適用中國國家標準（CNS ) Α4規格（210X297公釐）-267 - (請先閱讀背面之注意事項再填寫本頁 、1·、 1T-This paper size applies Chinese National Standard (CNS) A4 gauge (210X 297mm) -266-524805 A7 B7 V. Description of the invention (264) The title compound of Preparation Example 4 and 4-bromobenzyl Chlorine was prepared according to the procedure of Preparation 15B, and it was a yellow oil (54%). 5 (CDC 1 3): 0.94 (3H, t), 1.58 (3 Η, t), 1. 7 3 (2 Η, m), 2. 〇8 (2 Η, t), 4 · 〇8 (2 Η, q), 5 · 5 Ο (2 Η, s), 7 · 〇 8 (4 Η, m), 7 · 4 4 (3 Η, m), 8.38 (lH, d), 10.89 (lH, s) ° LR M S: m / z 484 (M + 18) +. Preparation Example 9 0 1- (2-Cyano; yl) -5- (2-Ethoxyphenyl) -3-n-propyl-1,6-dihydro-7H —Sit down and [4,3 — d ] Pyrimidine-7-one was prepared from the title compound of Preparation Example 14 and 2-cyanobenzyl bromide according to the procedure of Preparation Example 15D as a solid (17%). Obtained by element analysis: C, 69 · 58; H, 5 · 60; N, 16 · 9 0. C24H23N502 calculated 値 C, 69.72; Η, 5.61; N, 16.94%. 5 (CDCl3): 1.03 (3H, t), this paper size applies to Chinese National Standard (CNS) A4 specification (210X297 mm) -267-(Please read the precautions on the back before filling this page, 1

經濟部中央標準局員工消費合作社印製 524805 經濟部中央標準局員工消費合作社印製 A7 B7 五、發明説明（265) 1 . 6 〇（3 Η，t )， 1 · 9 〇（2 Η，m )， 2 · 9 8 ( 2 Η，t )， 4 · 3 〇（2 Η，q )， 6 ·〇 3 ( 2 Η，s )， 7 ·〇 5 ( 2 Η，m )， 7 · 1 6 ( 1 Η，m )， 7 · 3 6 ( 1 Η，m )， 7 · 4 5 ( 2 Η，m )， 7 · 6 8 ( 1 Η，d )， 8 · 5 4 ( 1 Η，d )， 11.2〇（lH，s)° LRMS:m/z 414(M+1)+。 製備例9 1 1 一（4 一胺羰基苄基）—5— (2 —乙氧苯基）— 3 -正丙基一 1，6—二氫一 7H -吡唑並〔4，3 — d 〕嘧啶一 7 —酮 由製備例14之標題化合物及4-胺羰基苄基氯依製 備例15A之步驟製得，呈白色固體（73%)。 元素分析實測値：C，6 6 · 2 2 ; Η，5 · 8 1 ; N， 16 · 0 6 。C24H25N5〇3計算値 C ，66 · 81 ; Η，5·84;Ν，16·23%。 5 ( C D C 1 a ) :1.02(3H，t)， 本紙張尺度適用中國國家標準（CNS ) A4規格（210X297公釐）-268 - (請先閱讀背面之注意事項再填寫本頁) .#衣·Printed by the Consumer Cooperative of the Central Standards Bureau of the Ministry of Economic Affairs 524805 Printed by the Consumer Cooperative of the Central Standards Bureau of the Ministry of Economic Affairs A7 B7 V. Description of the invention (265) 1.6 (3 Η, t), 1. 9 〇 (2 Η, m ), 2 · 9 8 (2 Η, t), 4 · 3 〇 (2 Η, q), 6 · 〇3 (2 Η, s), 7 · 〇5 (2 Η, m), 7 · 1 6 (1 Η, m), 7 · 3 6 (1 Η, m), 7 · 4 5 (2 Η, m), 7 · 6 8 (1 Η, d), 8 · 5 4 (1 Η, d) , 11.20 (lH, s) ° LRMS: m / z 414 (M + 1) +. Production Example 9 1 1- (4-monoaminocarbonylbenzyl) -5— (2-ethoxyphenyl) -3—n-propyl-1,6-dihydro-7H-pyrazolo [4,3 — d ] Pyrimidine-7-one was prepared from the title compound of Preparation Example 14 and 4-aminocarbonylbenzyl chloride according to the procedure of Preparation Example 15A as a white solid (73%). Elemental analysis of plutonium: C, 6 6 · 2 2; plutonium, 5 · 8 1; N, 16 · 0 6. C24H25N503 calculated 値 C, 66.81; Η, 5.84; N, 16.23%. 5 (CDC 1 a): 1.02 (3H, t), this paper size applies Chinese National Standard (CNS) A4 specification (210X297 mm) -268-(Please read the precautions on the back before filling this page). # 衣·

524805 A7 經濟部中央標準局員工消費合作社印製 B7 五、發明説明（266) 1 · 6 2 ( 3 Η，t )， 1 · 9 〇（2 Η，m )， 2 · 9 6 ( 2 Η，t )， 4 · 3 0 ( 2 Η，q )， 5 · 5 9 ( 1 Η，s )， 5 . 8 2 ( 2 Η，s )， 6 · 0 〇（1 Η，s )， 7 ·〇 5 ( 1 Η，d )， 7 · 1 6 ( 1 Η，m )， 7 · 4 5 ( 3 Η，m )， 7 . 7 8 ( 2 Η，d )， 8 · 5 2 ( 1 Η，d )， 11.24(lH，s)。 L R M S ： m / z 432 (M+1)+。 製備例9 2 2 —（4 —胺羰基苄基）％ 5— (2 —乙氧苯基）— 3 -正丙基—2，6 -二氫—7H —吡唑並〔4，3 — d 〕嘧π定一 7 -酮 由製備例1 4之標題化合物及4 -胺羰基苄基溴依製 備例15B之步驟製得，呈白色固體（47%)。， 元素分析實測値：C，6 6 · 1〇；Η，5 · 7 8 ; N， 16 · 02 。 C24H25N5〇3; 〇·〇7CH3C〇2CH2CH3 計算値 C ，66 · 63 ; (讀先閱讀背面之注意事項再填寫本頁) ▼ 訂524805 A7 Printed by the Consumer Cooperative of the Central Standards Bureau of the Ministry of Economic Affairs B7 V. Description of the invention (266) 1 · 6 2 (3 Η, t), 1 · 9 〇 (2 Η, m), 2 · 9 6 (2 Η, t), 4 · 3 0 (2 Η, q), 5 · 5 9 (1 Η, s), 5.8 2 (2 Η, s), 6 · 0 〇 (1 Η, s), 7 · 〇 5 (1 Η, d), 7 · 1 6 (1 Η, m), 7 · 4 5 (3 Η, m), 7. 7 8 (2 Η, d), 8 · 5 2 (1 Η, d ), 11.24 (lH, s). L R M S: m / z 432 (M + 1) +. Preparation Example 9 2 2 — (4-aminocarbonylbenzyl)% 5— (2-ethoxyphenyl) —3-n-propyl-2,6-dihydro-7H —pyrazolo [4,3 — d ] Pyridine-7-one was prepared from the title compound of Preparation 14 and 4-aminocarbonylbenzyl bromide according to the procedure of Preparation 15B as a white solid (47%). , Elementary analysis: 値: C, 6 6 · 10; Η, 5 · 7 8; N, 16 · 02. C24H25N5〇3; 〇 · 〇7CH3C〇2CH2CH3 Calculate 値 C ， 66 · 63; (Read the precautions on the back before filling this page) ▼ Order

本紙張尺度適用中國國家標準（CNS ) A4規格（21〇Χ；297公釐）-269 - 524805 A7 B7 五、發明説明（267) Η (5 2 4 7 7 7 7 7 8 (C • 5 • 7 • 8 .3 • 5 • 6 .1 •〇 .1 • 2 • 4 .7 .4 • 8 9 ; Ν，1 ( D C 1 3 ):〇· •〇 0 %。 1 5 ( 3 H ， t ) 9 ( 3 Η 4 ( 2 Η 6 ( 2 Η 〇（2 Η 9 ( 2 Η 8 ( 1 Η 2 ( 1 Η 3 ( 1 Η 2 ( 1 Η 6 ( 2 Η 5 ( 1 Η 9 ( 2 Η 〇（1 Η t ) m ) t ) Q ) s ) s ) s ) d ) m ) d ) m ) d ) d ) (請先閱讀背面之注意事項再填寫本頁) 經濟部中央標隼局員工消費合作社印製 1 〇· 9 2 ( 1 H，s )。 L R M S ： m / z 4 3 2 ( M + 1 ) 製備例9 3 5 —（2 —乙氧苯基）一1— (2 —硝苄基）一 3 — 正丙基—1，6 —二氫—7H —吡唑並〔4，3 — d〕嘧 口定一 7 -酮 由製備例1 4之標題化合物及2 -硝苄基氯依製備例 15A之步驟製得，呈灰色固體（39%)。 本紙張尺度適用中國國家標準（CNS ) A4規格（210X297公釐）-270 _ 524805 經濟部中央標準局員工消費合作社印製 A7 B7 五、發明説明（268) 元素分析實測値：C，6 3 · 6 2 ; Η，5 · 3 2 ; N， 16 · 0 7。C23H23N5〇4 計算値 C，63 · 73 ； Η，5·35;Ν，16·16%。 5(CDCl3):l.〇5(3H，t)， 1 · 6 〇（3 Η，t )， 1 . 9 2 ( 2 Η，m )， 3 ·〇〇（2 Η ， t )， 4 · 3 2 ( 2 Η，q )， 6 . 2 5 ( 2 Η，s )， 6 · 7 〇（1 Η，d )， 7 ·〇 6 ( 1 Η，d )， 7 · 1 8 ( 1 Η，m )， 7 · 4 5 ( 3 Η，m )， 8 · 1 4 ( 1 Η，d )， 8 · 5 4 ( 1 Η，d )， 11.24(lH，s)。 LRMS:m/z 434(M+1)+。 製備例9 4 1— (2 —硝子基）—5— (2 —乙氧苯基）—3 — 正丙基一 1 ，6 —二氫一 7H —吡唑並〔4，3 — d〕嚼 D定—7 —酮 由製備例1 2之標題化合物及2 -硝苄基氯依製備例 15A之步驟製得，呈白色固體（46%)。 本紙張尺度適用中國國家標準（CNS)A4規格（210X 297公釐）-271 - (請先閱讀背面之注意事項再填寫本頁)This paper size applies Chinese National Standard (CNS) A4 specification (21〇 ×; 297 mm) -269-524805 A7 B7 V. Description of the invention (267) Η (5 2 4 7 7 7 7 7 8 (C • 5 • 7 • 8 .3 • 5 • 6 .1 • 〇.1 • 2 • 4 .7 .4 • 8 9; Ν, 1 (DC 1 3): 〇 • 〇0%. 1 5 (3 H, t ) 9 (3 Η 4 (2 Η 6 (2 Η 〇 (2 Η 9 (2 Η 8 (1 Η 2 (1 Η 3 (1 Η 2 (1 Η 6 (2 Η 5 (1 Η 9 (2 Η 〇 (1 Η t) m) t) Q s s s s s s d d) m d d) m d d d) (Please read the notes on the back before filling out this page) Staff Consumption Cooperative prints 1 · 09 2 (1 H, s). LRMS: m / z 4 3 2 (M + 1) Preparation Example 9 3 5 — (2-ethoxyphenyl) -1— (2-nitrobenzyl) A) 3-n-propyl-1,6-dihydro-7H-pyrazolo [4,3-d] pyrimidin-7-one from the title compound of Preparation Example 4 and 2-nitrobenzyl chloride It was prepared according to the procedure of Preparation 15A, and it was gray solid (39%). This paper size is applicable to China National Standard (CNS) A4 specification (210X297 mm) -270 _ 524805 Central Standard of the Ministry of Economy Printed by the Consumer Cooperatives of the Bureau A7 B7 V. Description of the invention (268) Elementary analysis and actual measurement 値: C, 6 3 · 6 2; Η, 5 · 3 2; N, 16 · 0 7. C23H23N50 04 Calculate 値 C, 63 73; Η, 5.35; N, 16.16%. 5 (CDCl3): 1.05 (3H, t), 1.6 〇 (3 Η, t), 1. 9 2 (2 Η, m), 3 · 〇〇 (2 Η, t), 4 · 3 2 (2 Η, q), 6. 2 5 (2 Η, s), 6 · 7 〇 (1 Η, d), 7 · 〇 6 (1 Η, d), 7 · 1 8 (1 Η, m), 7 · 4 5 (3 Η, m), 8 · 1 4 (1 Η, d), 8 · 5 4 (1 Η, d ), 11.24 (lH, s). LRMS: m / z 434 (M + 1) +. Preparation Example 9 4 1— (2-Nitronyl) -5— (2-Ethoxyphenyl) -3—n-propyl 1,2,6-dihydro-7H-pyrazolo [4,3-d] chrysene-7-one was prepared from the title compound of Preparation 12 and 2-nitrobenzyl chloride according to the procedure of Preparation 15A Yes, it was a white solid (46%). This paper size applies to China National Standard (CNS) A4 (210X 297 mm) -271-(Please read the precautions on the back before filling this page)

524805 經濟部中央標隼局員工消費合作社印製 A7 B7 五、發明説明（269) 5(CDCl3):l.〇2(3H，t)， 1 · 1 5 ( 3 Η，t )， 1 · 9 〇（2 Η，m )， 2 ·〇 0 ( 2 Η，m )， 2 · 9 9 ( 2 Η，m )， 4 · 2 〇（2 Η，t )， 6 · 2 4 ( 2 Η，s )， 6 · 6 6 ( 1 Η，d )， 7 ·〇 4 ( 1 Η，d )， 7 · 1 8 ( 1 Η，m )， 7 . 4 5 ( 3 Η，m )， 8 · 1 4 ( 1 Η，d )， 8 · 5 4 ( 1 Η，d )， 11.26(lH，s)，。 LRMS:m/z 448 (M+1)+。 製備例9 5 5 -（2 —乙氧苯基）—1— (4 —硝苄基）一3 — 正丙基一 1 ，6 —二氫—7H —吡唑並〔4，3 - d〕嘧 D定—7 —酮 由製備例1 4之標題化合物及4 -硝苄基氯依製備例 1 5 A之步驟製得，呈晶狀固體（6 1 % )。 元素分析實測値：C，6 3 · 5 9 ; Η，5 · 3 1 ; N， 16 · 0 2 。C23H23N5〇4 計算値 C' 63 · 73 ; 本紙張尺度適用中國國家標準（CNS ) A4規格（210X297公釐）-272 - (請先閲讀背面之注意事項再填寫本頁)524805 Printed by the Consumer Cooperatives of the Central Bureau of Standards of the Ministry of Economic Affairs A7 B7 V. Invention Description (269) 5 (CDCl3): 1.02 (3H, t), 1 · 1 5 (3 3, t), 1 · 9 〇 (2 Η, m), 2 〇0 (2 Η, m), 2 · 9 9 (2 Η, m), 4 · 2 〇 (2 Η, t), 6 · 2 4 (2 Η, s ), 6 · 6 6 (1 Η, d), 7 · 〇 4 (1 Η, d), 7 · 1 8 (1 Η, m), 7.4 5 (3 Η, m), 8 · 1 4 (1 Η, d), 8 · 5 4 (1 Η, d), 11.26 (lH, s),. LRMS: m / z 448 (M + 1) +. Preparation Example 9 5 5-(2-Ethoxyphenyl) -1- (4-nitrobenzyl) -3-n-propyl-1,6-dihydro-7H-pyrazolo [4,3-d] Pyrimidin-7-one was prepared from the title compound of Preparation Example 4 and 4-nitrobenzyl chloride according to the procedure of Preparation Example 15A, and was a crystalline solid (61%). Elemental analysis: 値: C, 6 3 · 5 9; Η, 5 · 3 1; N, 16 · 0 2. C23H23N5〇4 calculation 値 C '63 · 73; This paper size is applicable to China National Standard (CNS) A4 specification (210X297 mm) -272-(Please read the precautions on the back before filling this page)

524805 A7 B7 五、發明説明（270) Η，5·35;Ν，16·16%。 5(CDCl3):l.〇2(3H，t)， 1 · 6 0 ( 3 Η，t )， 1 · 8 8 ( 2 Η，m )， 2 · 9 7 ( 2 Η，t )， 4 · 3 〇（2 Η，q )， 5 · 8 4 ( 2 Η，s )， 7 · 0 4 ( 1 Η，d )， 7 · 1 6 ( 1 Η，m )， 7 · 4 6 ( 1 Η，m )， 7 · 5 2 ( 2 Η，d )， 8 · 1 8 ( 2 Η，d )， 8 · 5 〇（1 Η，d )， 11.26(lH，s)° LRMS:m/z 434 (M+1)+。 製備例9 6 經濟部中央標準局員工消費合作社印製 (請先閲讀背面之注意事項再填寫本頁) 5— (2 —乙氧苯基）一2— (4—硝苄基）—3 — 正丙基一 2，6 —二氫一 7H —吡唑並〔4，3 — d〕嘧 啶一 7 —酮 由製備例1 4之標題化合物及4 -硝苄基溴依製備例 15C之步驟製得，呈黃色固體（30%)。 5 ( C D C 1 a ):〇.98(3H，t)， 1 · 6 〇（3 Η ， t )， 本紙張尺度適用中國國家標準（CNS ) A4規格（210X 297公釐）-273 - 524805 經濟部中央標準局員工消費合作社印製 A7 B7 五、發明説明（271) 1 · 7 6 ( 2 Η，m )， 2 · 9 〇（2 Η，t )， 4 · 3 〇（2 Η，q )， 5 · 6 4 ( 2 Η，s )， 7 · Ο 5 ( 1 Η，d )， 7 · 1 4 ( 1 Η，m )， 7 · 3 6 ( 2 Η，d )， 7 · 4 6 ( 1 Η，m )， 8 · 2 Ο ( 2 Η，d )， 8 · 4 1 ( 1 Η，d )， 1 〇· 9 8 ( 1 Η，s ) ° L R Μ S ： m / ζ 434 (Μ+1)+。 製備例9 7 1— (2— 胺苄基）—5 — {5 —〔4— (2 —第三 丁基二甲基矽烷氧乙基）六氫吡畊一 1 一基磺醯基〕一 2 一正丙氧苯基} — 3 -正丙基—1，6 -二氫—7Η -吡 唑並〔4，3 — d〕嘧π定一7 -酮 將咪唑（39mg，〇· 57mmo 1)及第三丁基 二甲矽烷基氯（69mg，〇 · 46mmo 1)加入一攪 拌中而含有實施例5 3標題化合物（2 3 3 m g， 0 · 38mmo 1)及二氯甲烷（4ml)的溶液裡，然 後在室溫下攪拌此混合物2 0小時。接著加水（5 m 1 ) ，水相部份分離出來後用二氯甲烷（2 0 m 1 )萃取，合 本紙張尺度適用中國國家標準（CNS ) A4規格（210X297公釐）-274 - (請先閱讀背面之注意事項再填寫本頁) 訂524805 A7 B7 V. Description of the invention (270) Η, 5.35; N, 16.16%. 5 (CDCl3): 1.02 (3H, t), 1 · 6 0 (3 Η, t), 1 · 8 8 (2 Η, m), 2 · 9 7 (2 Η, t), 4 · 3 0 (2 Η, q), 5 · 8 4 (2 Η, s), 7 · 0 4 (1 Η, d), 7 · 1 6 (1 Η, m), 7 · 4 6 (1 Η, m), 7 · 5 2 (2 Η, d), 8 · 1 8 (2 Η, d), 8 · 5 〇 (1 Η, d), 11.26 (lH, s) ° LRMS: m / z 434 ( M + 1) +. Preparation Example 9 6 Printed by the Consumer Cooperatives of the Central Bureau of Standards, Ministry of Economic Affairs (please read the precautions on the back before filling out this page) 5— (2-ethoxyphenyl) —2— (4-nitrobenzyl) —3 — N-propyl-2,6-dihydro-7H-pyrazolo [4,3-d] pyrimidin-7-one was prepared from the title compound of Preparation 14 and 4-nitrobenzyl bromide according to the procedure of Preparation 15C It was obtained as a yellow solid (30%). 5 (CDC 1 a): 0.98 (3H, t), 1.6 〇 (3 Η, t), this paper size applies Chinese National Standard (CNS) A4 specification (210X 297 mm) -273-524805 Economy Printed by A7 B7, Consumer Cooperatives of the Ministry of Standards of the People's Republic of China V. Invention Description (271) 1 · 7 6 (2 Η, m), 2 · 9 〇 (2 Η, t), 4 · 3 〇 (2 Η, q) , 5 · 6 4 (2 Η, s), 7 · Ο 5 (1 Η, d), 7 · 1 4 (1 Η, m), 7 · 3 6 (2 Η, d), 7 · 4 6 ( 1 Η, m), 8 · 2 Ο (2 Η, d), 8 · 4 1 (1 Η, d), 1 · 9 8 (1 Η, s) ° LR MS: m / ζ 434 (Μ +1) +. Preparation Example 9 7 1— (2—Aminobenzyl) —5 — {5 — [4— (2—Third-butyldimethylsilyloxyethyl) hexahydropyridine—1—Sulfosulfonyl] — 2 mono-n-propoxyphenyl} — 3 -n-propyl-1,6-dihydro-7Η-pyrazolo [4,3-d] pyrimidine-7-one imidazole (39mg, 0.57mmo 1 ) And tertiary butyldisilyl chloride (69 mg, 0.46 mmo 1) were added to a stirring solution containing the title compound of Example 5 3 (2 3 3 mg, 0 · 38 mmo 1) and dichloromethane (4 ml). The solution was then stirred at room temperature for 20 hours. Then add water (5 m 1), the water phase is separated, and then extracted with dichloromethane (20 m 1). The paper size applies the Chinese National Standard (CNS) A4 specification (210X297 mm) -274-(Please (Please read the notes on the back before filling out this page)

524805 經濟部中央標準局員工消費合作社印製 A7 B7 五、發明説明（272) 倂的有機溶液乾燥（N a 2 S 0 4 )後減壓蒸發，所得黃色 油狀物以管柱層析法利用戊烷：乙酸乙酯（1 : 1 )爲沖 提液於矽膠上純化而得標題化合物（2 1 2 m g )，呈無 油狀物。 5 ( C D C 1 a ):〇.〇〇（6H，s)， 0 · 8 5 ( 9 Η，s )， 1 ·〇 2 ( 3 Η，t )， 1 · 2 Ο ( 3 Η，t )， 1 · 8 8 ( 2 Η，m )， 2 ·〇 6 ( 2 Η，m )， 2 · 5 2 ( 2 Η，t )， 2 · 6 2 ( 4 Η，m )， 2 · 9 5 ( 2 Η，t )， 3 ·〇 8 ( 4 Η，m )， 3 · 6 6 ( 2 Η，t )， 4 · 2 6 ( 2 Η，t )， 5 · 7 9. ( 2 Η，s )， 7 · 1 8 ( 2 Η，m )， 7 · 3 6 ( 1 Η，m )， 7 · 6 〇（1 Η，d )， 7 · 7 〇（1 Η，d )， 7 · 8 2 ( 1 Η，d )， 8.8〇（lH，s)， 9 · 7 〇（1 Η，s )， 本紙張尺度適用中國國家標準（CNS ) A4規格（21〇X 297公釐）_ 275 (請先閱讀背面之注意事項再填寫本頁)524805 A7 B7 printed by the Consumer Cooperative of the Central Standards Bureau of the Ministry of Economic Affairs 5. Description of the invention (272) The organic solution of tritium is dried (N a 2 S 0 4) and evaporated under reduced pressure. Pentane: ethyl acetate (1: 1) was purified on silica gel as the eluent to obtain the title compound (2 1 2 mg) as an oil-free substance. 5 (CDC 1 a): 〇〇〇 (6H, s), 0. 8 5 (9 Η, s), 1 〇2 (3 Η, t), 1 · 2 0 (3 Η, t), 1 · 8 8 (2 Η, m), 2 · 〇 6 (2 Η, m), 2 · 5 2 (2 Η, t), 2 · 6 2 (4 Η, m), 2 · 9 5 (2 Η, t), 3 · 〇8 (4 Η, m), 3 · 6 6 (2 Η, t), 4 · 2 6 (2 Η, t), 5 · 7 9. (2 Η, s), 7 · 1 8 (2 Η, m), 7 · 3 6 (1 Η, m), 7 · 6 〇 (1 Η, d), 7 · 7 〇 (1 Η, d), 7 · 8 2 (1 Η, d), 8.8 (lH, s), 9 · 7 (1 Η, s), this paper size is applicable to China National Standard (CNS) A4 specification (21〇X 297 mm) _ 275 (Please read first (Notes on the back then fill out this page)

、1T, 1T

524805 A7 B7 經濟部中央標準局員工消費合作社印掣 五、發明説明（273) 10.98(1H，S)。LRMS:m/z 724 (M+1)+。 製備例9 8 5 一丨5 —〔4一（2 —第三丁基二甲基矽烷氧乙基 )六氫吡畊一 1 一基磺醯基〕一 2 -正丙氧苯基} 一1一 (2 —甲烷磺醯胺基苄基）一 3 一正丙基一 1，6 一二氫 一 7 Η —吡唑並〔4，3 - d〕嘧啶一 7 —酮 將甲院磺酿氯（24//1 ，0 · 30mmo 1)加入 一攪拌中且以冰冷卻而含有製備例9 7標題化合物（200mg ’ 〇 · 28mmo 1)及吡啶（3ml)的溶 液裡，於室温下攪拌此混合物2 〇小時，然後減壓蒸發。 殘餘物以水（1 〇 m丨）處理過，再將此懸浮液用乙酸乙 醋（總量4 0 m 1 )萃取。萃取液合倂後乾燥（ N a 2 S〇4 ) ’再減壓蒸發而得黃色油狀物，以管柱層析 法利用戊院：乙酸乙酯（1 : 1 )爲沖提液爲矽膠上純化 而得無色油狀標題化合物（1 4 5mg )。 5 ( C D C 1 3 ):〇.〇〇（6H，s)， 〇.85(9H，s)， 1.02(3H，t)， 1.20(3H，t)，1.88(2H，m)， 2.06 (2H，m)， 2 · 5 2 ( 2 H，t )， (讀先閱讀背面之注意事項再填寫本頁) .··524805 A7 B7 Printed by the Consumer Cooperatives of the Central Standards Bureau of the Ministry of Economic Affairs 5. Description of the invention (273) 10.98 (1H, S). LRMS: m / z 724 (M + 1) +. Preparation Example 9 8 5 a 5-[4-(2-third butyldimethylsilyloxyethyl) hexahydropyridine-1-sulfosulfanyl]-2-n-propoxyphenyl}-1 Mono (2-methanesulfonamidobenzyl) -3 3-n-propyl-1,6-dihydro-7 7-pyrazolo [4,3-d] pyrimidine-7-keto (24 // 1, 0. 30mmo 1) was added to a solution containing the title compound of Preparation Example 7 (200 mg '0. 28mmo 1) and pyridine (3ml) under ice-cooling, and the mixture was stirred at room temperature 20 hours, then evaporated under reduced pressure. The residue was treated with water (10 m) and the suspension was extracted with ethyl acetate (total 40 m 1). The extract was combined and dried (N a 2 S〇4) ', and then evaporated under reduced pressure to obtain a yellow oil. The column chromatography method was used E: ethyl acetate (1: 1) as the eluent was silicone The title compound was purified as a colorless oil (145 mg). 5 (CDC 1 3): 0.000 (6H, s), 0.85 (9H, s), 1.02 (3H, t), 1.20 (3H, t), 1.88 (2H, m), 2.06 (2H , M), 2 · 5 2 (2 H, t), (read the precautions on the back before filling in this page). ··

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本紙張尺度適用中國國家標準（CMS ) A4規格（21 OX 297公釐） -276- 524805 A7 B7 五、發明説明（274) 2 · 6 2 ( 4 Η，m )， 2 · 9 5 ( 2 Η，t )， 3 · Ο 8 ( 4 Η，m )， 3 · 6 6 ( 2 Η，t )， 4 · 2 6 ( 2 Η，t )， 5 · 7 9 ( 2 Η，s )， 7 · 1 8 ( 2 Η，m )， 7 · 3 6 ( 1 Η，m )， 7 · 6 〇（1 Η，d )， 7 · 7 〇（1 Η，d )， 8 · 8 〇（1 Η，s )， 9 . 7 Ο ( 1 Η，s )， l〇.98(lH，s)。 LRMS:m/z 8 0 2 ( Μ + 1 ) 製備例9 9 5 — (2 —乙氧苯基）—3 —正丙基一 1— (4 —胺 磺醯基苄基）—1，6 —二氫- 7Η —吡唑並〔4，3 — (讀先閱讀背面之注意事項再填寫本頁) 經濟部中央標準局員工消費合作社印製 d〕嘧啶一7 酮 由製備例1 4之標題化合物及4 -胺磺醯基苄基氯（ J. Med. Chem.，1 986，以_，1814 )依製備例1 5 A之步驟製 得，呈固體（5 1 % )。 元素分析實測値：C，5 8 · 7 8 ; Η，5 · 3 7 ; N， 14· 83。C23H25N5〇4S 計算値 C， 本纸張尺度適用中國國家標準（CNS ) A4規格（210X297公釐）-277 _ 524805 經濟部中央標準局員工消費合作社印製 A7 五、發明説明（275) 59·〇8;Η，5·39;Ν，14.98%。 5(DMS〇d6):〇.9〇（3H，t)， 1 · 3 2 ( 3 Η，t )， 1 · 7 4 ( 2 Η，m )， 2 · 7 9 ( 2 Η，t )， 4 · 1 4 ( 2 Η，q )， 5 · 7 8 ( 2 Η，s )， 7 ·〇 4 ( 1 Η，m )， 7 · 1 6 ( 1 Η，d )， 7 · 2 8 ( 2 Η，s )， 7 · 3 8 ( 2 Η，d )， 7 · 4 5 ( 1 Η，m )， 7 · 6 6 ( 1 Η，d )， 7 · 7 8 ( 2 Η，d )， 12.〇2(lH，s)。 LRMS .m / z 468 (M+l)+。 製備例1〇〇 1—苄氧羰甲基一5 — (2 —正丙氧苯基）—3 —正 丙基—1，6 —二氫—7H — d比π坐並〔4，3 — d〕喃D定 一 7 —酮 由製備例1 2之標題化合物及溴乙酸苄酯依製備例 15D之步驟製得，呈白色固體（28%)。 (5(CDCl3)：l.〇2(3H^t)^ (請先閱讀背面之注意事項再填寫本頁)This paper size applies the Chinese National Standard (CMS) A4 specification (21 OX 297 mm) -276- 524805 A7 B7 V. Description of the invention (274) 2 · 6 2 (4 Η, m), 2 · 9 5 (2 Η , T), 3 · Ο 8 (4 Η, m), 3 · 6 6 (2 Η, t), 4 · 2 6 (2 Η, t), 5 · 7 9 (2 Η, s), 7 · 1 8 (2 Η, m), 7 · 3 6 (1 Η, m), 7 · 6 〇 (1 Η, d), 7 · 7 〇 (1 Η, d), 8 · 8 〇 (1 Η, s), 9.7 (1 H, s), 10.98 (lH, s). LRMS: m / z 8 0 2 (Μ + 1) Preparation Example 9 9 5 — (2 —ethoxyphenyl) — 3 —n-propyl — 1 — (4-aminosulfonylbenzyl) — 1, 6 —Dihydro-7Η —Pyrazolo [4,3 — (Read the precautions on the back before filling this page) Printed by the Consumer Cooperatives of the Central Bureau of Standards of the Ministry of Economic Affairs d] Pyrimidin-7 ketone by the title of Preparation Example 14 The compound and 4-sulfamoyl benzyl chloride (J. Med. Chem., 1 986, _, 1814) were prepared according to the procedure of Preparation 15A of Preparation Example 1 as a solid (51%). Elemental analysis: 値: C, 5 8 · 7 8; Η, 5 · 3 7; N, 14 · 83. C23H25N5〇4S Calculates ， C, this paper size applies Chinese National Standard (CNS) A4 specification (210X297 mm)-277 _ 524805 Printed by A7, Consumers Cooperative of the Central Standards Bureau of the Ministry of Economic Affairs 5. Description of invention (275) 8; H, 5.39; N, 14.98%. 5 (DMS〇d6): 0.90 (3H, t), 1.32 (3 Η, t), 1 · 7 4 (2 Η, m), 2 · 79 (2 Η, t), 4 · 1 4 (2 Η, q), 5 · 7 8 (2 Η, s), 7 · 〇 4 (1 Η, m), 7 · 1 6 (1 Η, d), 7 · 2 8 (2 Η, s), 7 · 3 8 (2 Η, d), 7 · 4 5 (1 Η, m), 7 · 6 6 (1 Η, d), 7 · 7 8 (2 Η, d), 12 〇2 (lH, s). LRMS .m / z 468 (M + l) +. Preparation Example 001—Benzyloxycarbonylmethyl-5— (2-n-propoxyphenyl) —3—n-propyl—1,6—dihydro—7H—d ratio satisfies [4,3 — d] Dan-7-ketone was prepared from the title compound of Preparation Example 12 and benzyl bromoacetate according to the procedure of Preparation Example 15D as a white solid (28%). (5 (CDCl3): 1.02 (3H ^ t) ^ (Please read the precautions on the back before filling this page)

、1T 本紙張尺度適用中國國家標準（CNS ) Α4規格（210X 297公釐）-278 - 經濟部中央標準局員工消費合作社印製 524805 五、發明説明（276) 1 . 1 7 ( 3 Η，t )， 1 · 9 〇（2 Η，m )， 2 · 0 2 ( 2 Η，m )， 2 · 9 7 ( 2 Η，t )， 4 · 1 9 ( 2 Η，t )， 5 · 2 1 ( 2 Η，s )， 5 · 4 2 ( 2 Η，s )， 7 ·〇 6 ( 1 Η，d )， 7 · 1 7 ( 1 Η，m )， 7 · 3 3 ( 5 Η，m )， 7 · 4 7 ( 1 Η，m )， 8 · 5 〇（1 Η，d )， 11.23(lH，s)° LRMS:m/z 461(M+1)+。 製備例1 0 1 1—羧甲基—5 —（2 -正丙氧苯基）一 3 —正丙基 一 1，6 —二氫—7H —吡唑並〔4，3 - d〕嘧啶—7 -酮 由製備例1 0 0之標題化合物依製備例6 9之步驟製 得，呈灰褐色固體（92%)。 5 ( C D C 1 a ) :1·〇4(3Η， ΐ) ， 1 · 1 8 ( 3 Η，t )， 1 · 9 1 ( 2 Η，m )， 本纸張尺度適用中國國家標準（CNS ) Α4規格（210Χ 297公釐)~_ 279 - (請先閱讀背面之注意事項再填寫本頁)、 1T This paper size is applicable to Chinese National Standard (CNS) A4 specification (210X 297 mm) -278-Printed by the Consumer Cooperatives of the Central Standards Bureau of the Ministry of Economic Affairs 524805 V. Description of the invention (276) 1. 1 7 (3 Η, t ), 1 · 9〇 (2 Η, m), 2 · 0 2 (2 Η, m), 2 · 9 7 (2 Η, t), 4 · 1 9 (2 Η, t), 5 · 2 1 (2 Η, s), 5 · 4 2 (2 Η, s), 7 · 〇6 (1 Η, d), 7 · 1 7 (1 Η, m), 7 · 3 3 (5 Η, m) , 7 · 4 7 (1 Η, m), 8 · 5 〇 (1 Η, d), 11.23 (lH, s) ° LRMS: m / z 461 (M + 1) +. Production Example 1 0 1 1-carboxymethyl-5 — (2-n-propoxyphenyl) —3—n-propyl-1,6-dihydro-7H —pyrazolo [4,3-d] pyrimidine— 7-Ketone was prepared from the title compound of Preparation Example 100 according to the procedure of Preparation Example 6 9 as a beige solid (92%). 5 (CDC 1 a): 1.04 (3Η, ΐ), 1 · 18 (3Η, t), 1 · 9 1 (2Η, m), this paper size applies Chinese National Standard (CNS) Α4 specification (210 × 297 mm) ~ _ 279-(Please read the precautions on the back before filling this page)

524805 _______B7^__ 五、發明説明（277) 2 · 0 1 ( 2 Η，m )， 2 · 9 7 ( 2 Η，t )， 4 · 2 〇（2 Η，t )， 5 · 4 1 ( 2 Η，s )， 7.〇6(lH，d)， 7.17(lH，m)， 7 · 4 8 ( 1 H，m )， 8 · 5 1 ( 1 H，d )， 11.36(lH，s)° LRMS :m/z 371 (M+l)+。 製備例1 0 2 1一（N-乙基胺羰甲基）一5_(2—正丙氧苯基 )—3 —正丙基—1，6 —二氫一 7H -吡唑並〔4，3 一 d〕嘧啶—7 —酮 經濟部中央標準局員工消費合作社印製 (請先閱讀背面之注意事項再填寫本頁) 在氮氣下將N —甲基嗎啉（91//1 ，0 · 83 mmo1)加入一攪拌中而含有製備例1〇1標題化合物 (93mg ，〇 · 23mmo 1)與二氯甲烷（5ml) 的溶液裡，並以冰浴冷卻。接著添加乙胺鹽酸鹽（2 4 mg，〇 · 30mmo 1) ，1 一羥苯並三唑水合物（ 41mg，〇.3〇mmol)，及 1— (3 —二甲胺丙 基）一 3 —乙基羰二亞胺鹽酸鹽（7 3mg，0 · 38m mol)，再令整個混合物升溫至室溫，於再攪拌2 0小 時後減壓蒸發。令殘餘物在乙酸乙酯（1 〇 m 1 )與2 Μ 本紙張尺度適用中國國家標準（CNS ) Α4規格（210Χ 297公釐） 524805 A7 B7 五、發明説明（278) 氫氯酸（1 0 m 1 )之間分配’水相分離出來用乙酸乙酯 (1 0 m 1 )洗過’再把合倂的有機溶液依續用飽和碳酸 氫鈉水溶液（1 0 m 1 )及鹽水（χ m 1 )洗之，經乾 燥（M g S 0 4 )後減壓蒸發而得標題化合物（8 9 m g ) ’呈乳固態狀（cream solid)。 5(CDCl3):l.〇3(3H，t)，1 · 1 0 ( 3 Η，t )， 1 · 1 8 ( 3 Η，t )， 經濟部中央標隼局員工消費合作社印製524805 _______ B7 ^ __ V. Description of the invention (277) 2 · 0 1 (2 Η, m), 2 · 9 7 (2 Η, t), 4 · 2 〇 (2 Η, t), 5 · 4 1 (2 Η, s), 7.06 (lH, d), 7.17 (lH, m), 7.4.8 (1H, m), 8.51 (1H, d), 11.36 (lH, s) ° LRMS: m / z 371 (M + l) +. Preparation Example 1 0 2 1- (N-ethylaminecarbonylmethyl) -5_ (2-n-propoxyphenyl) -3-n-propyl-1,6-dihydro-7H-pyrazolo [4, 3 a d) Printed by the Consumer Cooperative of the Central Standards Bureau of the Ministry of Economic Affairs, Pyrimidine-7-ketone (Please read the precautions on the back before filling this page) Under nitrogen, N-methylmorpholine (91 // 1, 0 · 83 mmo1) was added to a solution containing the title compound of Preparation Example 101 (93 mg, 0.23 mmo 1) and dichloromethane (5 ml) with stirring, and cooled in an ice bath. Ethylamine hydrochloride (24 mg, 0.30 mmo 1), 1-hydroxybenzotriazole hydrate (41 mg, 0.30 mmol), and 1- (3-dimethylaminepropyl)- 3-Ethylcarbonyldiimide hydrochloride (73 mg, 0.38 mol), the whole mixture was allowed to warm to room temperature, and after stirring for another 20 hours, it was evaporated under reduced pressure. Let the residue be in ethyl acetate (10m 1) and 2 megabytes. The paper size applies the Chinese National Standard (CNS) A4 specification (210 × 297 mm) 524805 A7 B7 V. Description of the invention (278) Hydrochloric acid (1 0 m 1), the aqueous phase was separated, washed with ethyl acetate (10 m 1), and the combined organic solution was successively used with a saturated sodium bicarbonate aqueous solution (10 m 1) and brine (χ m 1) After washing, it was dried (Mg S 0 4) and evaporated under reduced pressure to obtain the title compound (89 mg) 'is cream solid. 5 (CDCl3): 1.03 (3H, t), 1 · 10 (3 Η, t), 1 · 1 8 (3 Η, t), printed by the Consumer Cooperative of the Central Bureau of Standards, Ministry of Economic Affairs

018693268922S 90931220145 Μ ··········· r—H 122345677781L /IV \- /(V /(\ J1 Ji THX Ji THX J1 J1 THX XHX Ji THX ΤΓΛ TLi ΤΓ* THX ΤΓ- Thx ΤΓ- TLi TUI TLi Thx \1/ \)/ \)/ \)/ t m m mtssdmmd \)y \»y + M rv o 8 \)/ s 3 H z 1 \ cm 3 Ν 基 甲基羰 胺 N)/基 乙氧 甲 5 (讀先閱讀背面之注意事項再填寫本頁) 、1Τ 本紙張尺度適用中國國家標準（CNS ) A4規格（210X 297公釐）-281 - 524805 經濟部中央標準局員工消費合作社印製 A7 B7五、發明説明（279) 2 —正丙氧苯基）—3 —正丙基一 1，6 -二氨一 7H — 吡唑並〔4，3 — d〕嘧啶一 7 -酮 由製備例101之標題化合物及2-甲氧乙胺依製備 例1 0 2之步驟製得，呈白色粉末。 5(CDCl3):l.〇3(3H，t)， 1 · 1 8 ( 3 Η，t )， I. 88(2H，m)， 2 ·〇〇（2 Η ， m )， 2 · 9 8 ( 2 Η，t )， 3 · 2 9 ( 3 Η，s )， 3 . 4 2 ( 4 Η，m )， 4 · 2 1 ( 2 Η，t )， 5 · 2 9 ( 2 Η，s )， 6 . 4 5 ( 1 Η，s )， 7 · 0 4 ( 1 Η，d )， 7 . 1 5 ( 1 Η，d )， 7 · 4 8 ( 1 Η，m )， 8 · 5 〇（1 Η，d )， II. 27(lH，s)。 LRMS :m/z 428 (M+l)+。 製備例1〇4 1—(嗎啉一 4 一基羰甲基）—5 — (2 —正丙氧苯 基）—3 —正丙基—1，6 -二氫一 7H —吡唑並〔4， 本紙張尺度適用中國國家標準（CNS ) A4規格（210 X 297公釐）-282 - (請先閲讀背面之注意事項再填寫本頁) 衣.018693268922S 90931220145 Μ ········· r—H 122345677781L / IV \-/ (V / (\ J1 Ji THX Ji THX J1 J1 THX XHX Ji THX ΤΓΛ TLi ΤΓ * THX ΤΓ- ThLi ΤΓ- TLi TUI TLi Thx \ 1 / \) / \) / \) / tmm mtssdmmd \) y \ »y + M rv o 8 \) / s 3 H z 1 \ cm 3 Νmethyl methylcarbonyl N) / yl ethyl Oxymetholone 5 (Read the precautions on the back before filling this page), 1T This paper size is applicable to China National Standard (CNS) A4 specifications (210X 297 mm) -281-524805 Printed by the Staff Consumer Cooperative of the Central Standards Bureau of the Ministry of Economic Affairs A7 B7 V. Description of the invention (279) 2-n-propoxyphenyl) -3-n-propyl-1,6-diamino-7H-pyrazolo [4,3-d] pyrimidin-7-one is prepared from The title compound of Example 101 and 2-methoxyethylamine were prepared by the procedures of Preparation Example 102 as a white powder. 5 (CDCl3): 1.03 (3H, t), 1.18 (3H, t), 1.88 (2H, m), 2.0.0 (2H, m), 2.98 (2 Η, t), 3 · 2 9 (3 Η, s), 3.4 2 (4 Η, m), 4 · 2 1 (2 Η, t), 5 · 2 9 (2 Η, s) , 6. 4 5 (1 Η, s), 7 · 0 4 (1 Η, d), 7. 1 5 (1 Η, d), 7 · 4 8 (1 Η, m), 8 · 5 〇 ( 1 Η, d), II. 27 (lH, s). LRMS: m / z 428 (M + 1) +. Preparation Example 104—1- (morpholine-4 monocarbonylcarbonyl) -5— (2-n-propoxyphenyl) -3—n-propyl-1,6-dihydro-7H-pyrazolo [ 4. This paper size applies Chinese National Standard (CNS) A4 specification (210 X 297 mm) -282-(Please read the precautions on the back before filling this page).

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524805 A7 B7__ 五、發明説明（280) 3 — d〕嘧啶—7 —酮 由製備例1 0 1之標題化合物及嗎啉依製備例1〇2 之步驟製得，呈乳泡沬狀（9 5 % )。 (5 ( C D C 1 3 ) :l.〇3(3H，t)， 1 · 1 9 ( 3 Η，t )， I. 9〇（2H，m)， 2 · 0 〇（2 Η，m )， 2.98(2H，t)， 3·5〇 — 3.78(8H，m)， 4 · 1 9 ( 2 H，t )， 5 · 4 5 ( 2 H，s )， 7 ·〇 5 ( 1 H，d )， 7 · 1 8 ( 1 H，m )， 7.46(lH，m)， 8.5〇（lH，d)， II. 2〇（lH，s)。 LRMS:m/z 440 (M+1)+。 經濟部中央標準局員工消費合作社印製 (讀先閱讀背面之注意事項再填寫本頁) 製備例1〇5 2 -（N —乙基胺羰基甲基）_5 — (2 —正丙氧苯 基）一 3 -正丙基—2，6 —二氫—7H -吡唑並〔4， 3 — d〕嘧啶—7 -酮 由製備例6 9之標題化合物及乙胺鹽酸鹽依製備例 10 2之步驟製得，呈白色粉末（58%)。 本紙張尺度適用中國國家標準（CNS ) A4規格（210Χ 297公釐）_ 283 - 經濟部中央標準局員工消費合作社印製 524805 kl _ B7 五、發明説明（281) (5(CDCl3):l.l〇（3H，t)， 1 .〇 5 ( 3 Η，t )， 1 · 1 4 ( 3 Η，t )， 1 · 8 2 ( 2 Η，m )， 2 ·〇 2 ( 2 Η，m )， 3 ·〇〇（2 Η ， t )， 3 · 3 〇（2 Η，m )， 4 · 1 9 ( 2 Η，t )， 4 · 9 9 ( 2 Η，s )， 6 · 2 3 ( 1 Η，s )， 7 · 0 7 ( 1 Η，d )， 7 · 1 5 ( 1 Η，m )， 7 · 4 8 ( 1 Η，m )， 8 · 4 2 ( 1 Η，d )， 11.00(lH，s)° L R M S ： m / z 398 (M+1)+。 製備例1〇6 2 —〔N —（2 —甲氧乙基）胺羰基甲基〕一 5 —( 2 —正丙氧苯基）—3 —正丙基一 2，6 —二氫一 7H -吡唑並〔4，3 — d〕嘧啶一 7 —酮 由製備例6 9之標題化合物及2 -甲氧乙胺依製備例 1〇2之步驟製得，呈乳泡沬狀（7 4 % )。 ά ( C D C 1 3 ) :l.〇2(3H，t)， 本纸張尺度適用中國國家標準（CNS ) A4規格（210Χ 297公釐）~「284- (請先閱讀背面之注意事項再填寫本頁524805 A7 B7__ V. Description of the invention (280) 3-d] Pyrimidin-7-one was prepared from the title compound of Preparation Example 101 and morpholine according to the procedure of Preparation Example 102, and appeared in the form of a milk froth (9 5 %). (5 (CDC 1 3): 1.03 (3H, t), 1.19 (3H, t), 1.90 (2H, m), 2.0.0 (2H, m), 2.98 (2H, t), 3.50—3.88 (8H, m), 4.19 (2H, t), 5.4.5 (2H, s), 7.05 (1H, d) ), 7 · 18 (1 H, m), 7.46 (lH, m), 8.50 (lH, d), II. 2 (lH, s). LRMS: m / z 440 (M + 1) + Printed by the Consumer Cooperatives of the Central Bureau of Standards of the Ministry of Economic Affairs (Read the precautions on the back before filling out this page) Preparation Example 105 2-(N -ethylaminocarbonylmethyl) _5 — (2 -n-propoxybenzene A) 3 -n-propyl-2,6-dihydro-7H-pyrazolo [4, 3 — d] pyrimidin-7-one from the title compound of Preparation Example 6 and ethylamine hydrochloride according to the preparation example It is obtained by the procedure of 10 2 and is white powder (58%). This paper size is applicable to the Chinese National Standard (CNS) A4 specification (210 × 297 mm) _ 283-Printed by the Consumers' Cooperative of the Central Standards Bureau of the Ministry of Economic Affairs 524805 kl _ B7 V. Description of the invention (281) (5 (CDCl3): 110 (3H, t), 1.05 (3 Η, t), 1 · 1 4 (3 Η, t), 1 · 8 2 (2 Η , M), 2 · 2 (2 Η, m), 3 · 〇〇 (2 Η, t), 3 · 3 〇 (2 Η, m), 4 · 1 9 (2 Η, t), 4 · 9 9 (2 Η, s ), 6 · 2 3 (1 Η, s), 7 · 0 7 (1 Η, d), 7 · 1 5 (1 Η, m), 7 · 4 8 (1 Η, m), 8 · 4 2 (1 Η, d), 11.00 (lH, s) ° LRMS: m / z 398 (M + 1) +. Preparation Example 10 6 2 — [N — (2-methoxyethyl) aminocarbonylmethyl] A 5- (2-n-propoxyphenyl) -3-n-propyl-2,6-dihydro-7H-pyrazolo [4,3-d] pyrimidin-7-one was prepared from the title of Preparation Example 6 9 The compound and 2-methoxyethylamine were prepared according to the procedure of Preparation Example 102, and appeared as a milk foam (74%). (CDC 1 3): 1.02 (3H, t), this paper Standards apply Chinese National Standard (CNS) A4 specifications (210 × 297 mm) ~ "284- (Please read the precautions on the back before filling in this page

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524805 A7 B7 經濟部中央標準局員工消費合作社印製 五、發明説明（282) 1 · 1 5 ( 3 Η，t )， 1 · 8 4 ( 2 Η，m )， 2 ·〇〇（2 Η ， m )， 3 ·〇〇（2 Η ， t )， 3 · 2 8 ( 3 Η，s )， 3 . 4 〇（4 Η，m )， 4 · 1 9 ( 2 Η，t )， 5 ·〇〇（2 Η ， s )， 6 · 4 〇（1 Η，s )， 7 ·〇 6 ( 1 Η，d )， 7.16(lH，m)， ， 7 · 4 6 ( 1 H，m )， 8 · 4 3 ( 1 H，d )， l〇.97(lH，s)。 LRMS:m/z 428 (M+1)+。 製備例1〇7 2 —(嗎啉一 4 —基羰甲基）—5 — (2 —正丙氧苯 基）一3 —正丙基一 2，6 -二氣—7H —吼11坐並〔4， 3 — d〕嘧啶—7 -酮 由製備例6 9之標題化合物及嗎啉依製備例1 0 2之 步驟製得，呈白色泡沬狀（5 5 % )。 (5(CDCl3):l.〇5(3H，t)， 1 · 1 3 ( 3 Η，t )， (請先閱讀背面之注意事項再填寫本頁 衣·524805 A7 B7 Printed by the Consumer Cooperatives of the Central Standards Bureau of the Ministry of Economic Affairs. 5. Description of the invention (282) 1 · 1 5 (3 Η, t), 1 · 8 4 (2 Η, m), 2 · 〇〇 (2 ，, m), 3 · 〇〇 (2 Η, t), 3 · 2 8 (3 Η, s), 3.4 （(4 Η, m), 4 · 19 (2 Η, t), 5 · 〇 〇 (2 Η, s), 6 · 4 〇 (1 Η, s), 7 · 〇6 (1 Η, d), 7.16 (lH, m),, 7 · 4 6 (1 H, m), 8 · 4 3 (1 H, d), 10.97 (1 H, s). LRMS: m / z 428 (M + 1) +. Preparation Example 107—2— (morpholine-4-ylcarbonylmethyl) —5— (2-n-propoxyphenyl) —3—n-propyl—2,6—digas—7H—11 [4, 3 — d] Pyrimidin-7-one was prepared from the title compound of Preparation Example 69 and morpholine according to the procedure of Preparation Example 102, and was white foamy (55%). (5 (CDCl3): 1.05 (3H, t), 1 · 1 3 (3 Η, t), (Please read the precautions on the back before filling in this page.

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本紙張尺度適用中國國家標準（CNS ) Α4規格（210X297公釐）-285 - 524805 五、發明説明（283) ----- A7 B7This paper size applies to Chinese National Standard (CNS) A4 specification (210X297 mm) -285-524805 V. Description of invention (283) ----- A7 B7

4 5 7 7 7 8 1 L • 9 1 ( 2 Η，m )， • Ο Ο ( 2 Η，m )， • Ο 1 ( 2 Η，t )， • 6 6 ( 8 Η，m )， • 1 7 ( 2 Η，t )， • 2 Ο ( 2 Η，s )， • Ο 4 ( 1 Η，d )， • 1 5 ( 1 Η，m )， • 4 5 ( 1 Η，m )， .4 1 ( 1 Η，d )， 〇· 3 6 ( 1 Η，s )。 RMS:m/z 4 4 0 ( Μ + 1 ) 製備例1 Ο 8 4 — ( 2 S——氯丙醯基）嗎啉 在一攪拌中且以冰冷卻而含有s (—)一 2 -氯丙 (請先閲讀背面之注意事項再填寫本頁) ▼4 5 7 7 7 8 1 L • 9 1 (2 Η, m), • Ο Ο (2 Η, m), • Ο 1 (2 Η, t), • 6 6 (8 Η, m), • 1 7 (2 Η, t), • 2 Ο (2 Η, s), • Ο 4 (1 Η, d), • 1 5 (1 Η, m), • 4 5 (1 Η, m), .4 1 (1 Η, d), 0.36 (1 Η, s). RMS: m / z 4 4 0 (Μ + 1) Preparation Example 1 〇 8 4 — (2 S——chloropropylamidino) morpholine contains s (—)-2-chloro in a stirring and ice-cooling C (Please read the precautions on the back before filling this page) ▼

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酸 0 g 經濟部中央標準局員工消費合作衽印製 8 m m〇 與二氯甲烷（3〇m N〜甲基嗎啉（1 · 5 m 1 ， ’再添加1 一羥苯並三唑（Acid 0 g Consumption cooperation with employees of the Central Bureau of Standards of the Ministry of Economic Affairs printed 8 m m〇 with dichloromethane (30 m N ~ methylmorpholine (1.5 m 1, ′ plus 1-hydroxybenzotriazole (

1 · 483g ，11 ·〇mm〇 1)，然後在〇。(：下攪拌 4 5分鐘，接著添加嗎啉（2 · 4 m 1 ，2 7 · 6 mmol)，把冷卻浴移開，再於室溫下攪拌6 6小時， 然後減壓蒸發。令殘餘物在乙酸乙酯和水之間分配，把分 離出來的有機相用鹽水洗過，經乾燥（M g S〇4 )後減I 本紙張尺度適用中國國家標準（CNS ) Α4規格（21 ox297公釐）-286 - 524805 Μ ______Β7__ 五、發明説明（284) 蒸發。得到的黃色油狀物以管柱層析法利用己烷：乙酸乙 酯（3 : 1然後2 : 1 )之混合物爲沖提液於矽膠上純化 而得無色油狀標題化合物（5 7 m g )。 〔a〕2j+51° (C = 〇.l，CH3〇H)。 5 ( C D C 1 a ) :1.67(3H，d)， 3.42 — 3.8 9 (8H，m)， 4 · 5 3 ( 1 H，q )。 L R M S ： m / z 195 (M + NH4)+。 製備例1〇9 . 1 一〔 1 s —(嗎啉一4 一基羰基）乙基〕一 5 —（ 2 -正丙氧苯基）一 3 —正丙基—1，6 —二氫一 7H — 吡唑並〔4，3 — d〕嘧啶一 7 —酮 由製備例1 2與製備例1 0 8之標題化合物依製備例 1 5 B之步驟製得，呈白色泡沬狀（4 4 % )。 5 ( C D C 1 3 ) :l.〇2(3H，t)， (讀先閱讀背面之注意事項再填寫本頁)1 · 483 g, 1 · 0 mm 0 1), and then 0. (: Stir for 4 5 minutes, then add morpholine (2. 4 m 1, 2 7 · 6 mmol), remove the cooling bath, stir at room temperature for 6 6 hours, and then evaporate under reduced pressure. Partitioned between ethyl acetate and water, washed the separated organic phase with brine, dried (M g S〇4), minus I. This paper size applies the Chinese National Standard (CNS) A4 specification (21 ox297 mm) ) -286-524805 Μ ______ Β7__ 5. Description of the invention (284) Evaporation. The obtained yellow oil was subjected to column chromatography using hexane: ethyl acetate (3: 1 then 2: 1) as the eluent. Purification on silica gel gave the title compound (57 mg) as a colorless oil. [A] 2j + 51 ° (C = 0.1, CH3OH). 5 (CDC1a): 1.67 (3H, d), 3.42 — 3.8 9 (8H, m), 4 · 5 3 (1 H, q). LRMS: m / z 195 (M + NH4) +. Preparation Example 109.1. 1-[1 s — (morpholine-1 4-monocarbonyl) ethyl] -5- (2-n-propoxyphenyl) -3-n-propyl-1,6-dihydro-7H-pyrazolo [4,3-d] pyrimidine-7- Ketones are produced by the titles of Preparation Examples 12 and 108 The compound was prepared according to the procedure of Preparation Example 15B, and it was white foam (44%). 5 (CDC 1 3): 1.02 (3H, t), (Read the precautions on the back before reading (Fill in this page)

經濟部中央標準局員工消費合作社印製 m Η 9 9 9 9 9 ·/ Λ/ 1/ \!/ \)y \)/ Γ\ Λ7 tdmmm4tQ 5 5 5)·/ ^/n ? ) Η Η Η Η Η · Η H 33222321 '\ /IV /(V r\ /' _ /l\ /—V 88838008 17809421 ········ 11122346 本紙張尺度適用中國國家標準（CNS ) A4規格（210X297公釐）-287 - 524805 A7 B7 五、發明説明（285) 7 ·〇 6 ( 1 Η，d )， 7 · 1 6 ( 1 Η，m )， 7 · 4 6 ( 1 Η，m )， 8 · 5 2 ( 1 Η，d )， 11.24(lH，s)。 LRMS:m/z 454 (M+1)+。 製備例1 1〇 2 —〔IS —（嗎啉一 4 一基羰基）乙基〕—5 —（ 2 -正丙氧苯基）—3 —正丙基—2，6 —二氫一 7H — 吡唑並〔4，3 — d〕嘧啶一 7 —酮 由製備例1 2與製備例1 0 8之標題化合物依製備例 1 5 B之步驟製得，呈白色泡沬狀（3 3 % )。 5(CDCl3):l.〇5(3H，t)， 經濟部中央標準局員工消費合作社印製 5200808698 1890934615 ·····*···· 1112233345Printed by the Consumer Cooperative of the Central Standards Bureau of the Ministry of Economic Affairs m Η 9 9 9 9 9 · / Λ / 1 / \! / \) Y \) / Γ \ Λ7 tdmmm4tQ 5 5 5) · / ^ / n?) Η Η Η Η Η · Η H 33222321 '\ / IV / (V r \ /' _ / l \ / —V 88838008 17809421 ······· 11122346 This paper size applies to China National Standard (CNS) A4 (210X297) (Centi) -287-524805 A7 B7 V. Description of the invention (285) 7 · 〇6 (1 Η, d), 7 · 1 6 (1 Η, m), 7 · 4 6 (1 Η, m), 8 · 5 2 (1 H, d), 11.24 (lH, s). LRMS: m / z 454 (M + 1) +. Preparation Example 1 102— [IS — (morpholine-4 monocarbonylcarbonyl) ethyl ] -5— (2-n-propoxyphenyl) -3—n-propyl-2,6-dihydro-7H—pyrazolo [4,3-d] pyrimidin-7-one was prepared from Preparation Example 2 and The title compound of Preparation Example 108 was prepared according to the procedure of Preparation Example 15B and showed a white foam shape (33%). 5 (CDCl3): 1.05 (3H, t), Central Bureau of Standards, Ministry of Economic Affairs Printed by Employee Consumer Cooperatives 5200808698 1890934615 ········ 1112233345

Γν /IVΓν / IV

/(V /IV hhhhhhhhhh 3322222421 N \)/ NJ, \)/ \)/ \jx \)/ \)/ \lydmmmmmmtq (請先閱讀背面之注意事項再填寫本頁)/ (V / IV hhhhhhhhhh 3322222421 N \) / NJ, \) / \) / \ jx \) / \) / \ lydmmmmmmtq (Please read the precautions on the back before filling this page)

本紙張尺度適用中國國家標準（CNS ) Α4規格（210X297公釐）-288 - 經濟部中央榡準局員工消費合作衽印製 5248〇5This paper size applies to China National Standard (CNS) Α4 size (210X297 mm) -288-Printed by the Consumers' Cooperation of the Central Bureau of Standards of the Ministry of Economic Affairs 5248〇5

五、發明説明（286) 7 · 〇 6 ( 1 Η，d )， 7 · 4 7 ( 1 Η，m )， 8 · 4 0 ( 1 Η，d )， l〇.94(lH，s)。 LRMS :m/z 454 (M+l) 製備例1 1 1 4 一（ 2 R -氯丙醯基）嗎啉 由R— ( + ) — 2 —氯丙酸及嗎啉依製備例8之 步驟製得，呈淡黃色油狀物（1 6 % ) ° 〔a〕2j — 46。 （c = 〇.1，CH3〇H)° 5(CDCl3):1.69(3H，d)’ 3.49- 3 .87 (8 H，m)， 4 · 5 3 ( 1. Η，q )。 LRMS :m/z 195 (M + NH4)+。 製備例1 1 2 < 1一〔 1R—(嗎啉—4 —基鑛基）乙基〕一 5_ ( 2 -正丙氧苯基）一 3 —正丙基一1，6 -一氬一 7H — 11比唑並〔4，3 — d〕嘧啶一 7 —酮 由製備例1 2及製備例1 1 1之標題化合物依製備例 15B之步驟製得，呈黃色固體（8%)。 5 ( C D C 1 3 ) :l.〇2(3H，t)， 1.18 (3H，t)， ^紙張尺度適用中國國家標P cns ) A4規格（21 οχ 297公釐）_ 289 -V. Description of the invention (286) 7 · 〇6 (1Η, d), 7 · 4 7 (1Η, m), 8 · 4 0 (1Η, d), 10.94 (lH, s). LRMS: m / z 454 (M + l) Preparation Example 1 1 1 4 Mono (2 R -chloropropylamidino) morpholine R-(+)-2 -chloropropionic acid and morpholine according to the procedure of Preparation Example 8 Obtained as a pale yellow oil (16%) ° [a] 2j — 46. (C = 0.1, CH3OH) ° 5 (CDCl3): 1.69 (3H, d) '3.49-3.87 (8 H, m), 4 · 5 3 (1. Η, q). LRMS: m / z 195 (M + NH4) +. Preparation Example 1 1 2 < 1- [1R— (morpholine-4-yl-based) ethyl]-5_ (2 -n-propoxyphenyl)-3 -n-propyl-1,6--argon-1 7H-11 pyrazolo [4,3-d] pyrimidin-7-one was prepared from the title compound of Preparation Example 12 and Preparation Example 11 according to the procedure of Preparation Example 15B, as a yellow solid (8%). 5 (C D C 1 3): 1.02 (3H, t), 1.18 (3H, t), ^ Paper size applies Chinese national standard P cns) A4 specification (21 οχ 297 mm) _ 289-

經濟部中央標準局員工消費合作社印製 524805 kl B7 五、發明説明（287) 1 · 7 9 ( 3 Η，d )， 1 . 9 1 ( 2 Η，m )， 2 .〇 4 ( 2 Η，m )， 2 . 9 8 ( 2 Η，m )， 3.4 0 — 3.76 (8H，m)， 4 · 2 〇（2 H，t )， 6 · 1 9 ( 1 H，q )， 7 · 0 6 ( 1 H，d )， 7 · 1 8 ( 1 H，m )， 7 · 4 6 ( 1 H，m )， 8 · 5 2 ( 1 H，d )， 11.24(lH，s)。 LRMS:m/z 454(M+1)+。 製備例1 1 3 2 —〔 1R —（嗎啉一 4 一基羰基）乙基〕一 5 —( 2 —正丙氧苯基）一 3 —正丙基一 2，6 -二氫一 7H -吡唑並〔4，3 — d〕嘧啶—7 —酮 由製備例1 2及製備例1 1 1之標題化合物依製備例 15B之步驟製得，呈黃色粉末（23%)。 5(CDCl3):l.〇4(3H，t)， 1 · 1 4 ( 3 Η，t )， 1 · 8 2 ( 3 Η，d )， 1 · 9 2 ( 2 Η，m )， 本紙張尺度適用中國國家標準（CNS ) Α4規格（210X297公釐）-290 - (讀先閱讀背面之注意事項再填寫本頁)Printed by the Consumer Cooperatives of the Central Bureau of Standards of the Ministry of Economic Affairs 524805 kl B7 V. Description of Invention (287) 1 · 7 9 (3 Η, d), 1. 9 1 (2 Η, m), 2.04 (2 Η, m), 2. 9 8 (2 Η, m), 3.4 0 — 3.76 (8H, m), 4 · 2 0 (2 H, t), 6 · 1 9 (1 H, q), 7 · 0 6 (1 H, d), 7 · 1 8 (1 H, m), 7 · 4 6 (1 H, m), 8 · 5 2 (1 H, d), 11.24 (lH, s). LRMS: m / z 454 (M + 1) +. Production Example 1 1 3 2 — [1R — (morpholine-4 monocarbonylcarbonyl) ethyl] -5— (2-n-propoxyphenyl) -3—n-propyl-2,6-dihydro-7H— The pyrazolo [4,3-d] pyrimidin-7-one was prepared from the title compound of Preparation Example 12 and Preparation Example 11 according to the procedure of Preparation Example 15B, as a yellow powder (23%). 5 (CDCl3): 1.04 (3H, t), 1 · 1 4 (3 Η, t), 1 · 8 2 (3 Η, d), 1 · 9 2 (2 Η, m), this paper Standards apply to Chinese National Standard (CNS) Α4 specifications (210X297 mm) -290-(Read the precautions on the back before filling in this page)

經濟部中央標隼局員工消費合作社印製 524805 A7 B7 五、發明説明（288) 2 ·〇〇（2 Η ， m )， 2 · 9 9 ( 2 Η，m )， 3 · 3 〇（2 Η，m )， 3 · 4 8 ( 2 Η，m )， 3 · 6 3 ( 4 Η，m )， 4 · 1 9 ( 2 Η，t )， 5 . 5 9 ( 1 Η，q )， 7 ·〇 6 ( 1 Η，d )， 7 · 1 6 ( 1 Η，m )， 7 · 4 5 ( 1 Η，m )， 8 · 4 〇（1 Η，d )， l〇.95(lH，s)° LRMS :m/z 454 (M+l)+。 製備例1 1 4 1— (2 —嗎琳一 4 —基乙基）一 5 — (2 —正丙氧 苯基）一 3 —正丙基—1，6 —二氫—7H —吡唑並〔4 ，3 — d〕喃π定—7 -酮 由製備例1 2之標題化合物及4 一（ 2 —氯乙基）嗎 啉鹽酸鹽之自由鹼依製備例1 5 B之步驟製得，呈澄淸油 狀物（4 0 % )。 5 ( C D C 1 3 ) :l.〇3(3H，t)， 1 · 1 5 ( 3 Η，t )， 1 · 8 8 ( 2 Η，m )， 本紙張尺度適用中國國家標準（CNS ) Α4規格（21 ΟΧ 297公釐）-291 - (讀先閱讀背面之注意事項再填寫本頁)Printed by the Employees' Cooperative of the Central Bureau of Standards of the Ministry of Economic Affairs 524805 A7 B7 V. Description of the invention (288) 2 · 〇〇 (2Η, m), 2 · 9 9 (2Η, m), 3 · 3〇 (2Η , M), 3 · 4 8 (2 Η, m), 3 · 6 3 (4 Η, m), 4 · 1 9 (2 Η, t), 5. 5 9 (1 Η, q), 7 · 〇6 (1Η, d), 7 · 16 (1Η, m), 7 · 4 5 (1Η, m), 8 · 4〇 (1Η, d), 10.95 (1H, s ) ° LRMS: m / z 454 (M + 1) +. Production Example 1 1 4 1— (2 —Moryl—4-ylethyl) — 5 — (2 —n-propoxyphenyl) — 3 —n-propyl-1,6 —dihydro — 7H —pyrazolo [4,3 — d] pyridine-7-one was prepared from the title compound of Preparation Example 12 and the free base of 4- (2-chloroethyl) morpholine hydrochloride according to the procedure of Preparation Example 5B , As a clear oil (40%). 5 (CDC 1 3): 1.03 (3H, t), 1 · 1 5 (3 Η, t), 1 · 8 8 (2 Η, m), this paper size applies Chinese National Standard (CNS) Α4 Specifications (21 〇Χ 297mm) -291-(Read the precautions on the back before filling in this page)

524805 A7 B7 經濟部中央標準局員工消費合作社印製 五、發明説明（289) 2 · 0 〇（2 Η，m )， 2 · 5 2 ( 4 Η，m )， 2 · 8 8 ( 2 Η，t )， 2 · 9 3 ( 2 Η，t )， 3 · 6 2 ( 4 Η，m )， ) 4 · 1 9 ( 2 Η，t )， 4 · 7 〇（2 Η，t )， 7 ·〇 4 ( 1 Η，d )， 7 · 1 5 ( 1 Η，m )， 7 . 4 4 ( 1 Η，m )， 8 · 5 〇（1 Η，d )，‘ l〇.65(lH，s)° L R M S ： m / z 4 2 7 製備例1 1 5 2 — (2 —嗎啉—4 — 苯基）一 3 —正丙基-2， ，3 — d〕嘧啶—7 -酮 由製備例1 2之標題化 啉鹽酸鹽之自由鹼依製備例 沬狀（2 4 % )。 元素分析實測値：C，6 3 16 . 2 1。C23H31N: 算値 C，6 3 . 9 3 ; Η， (Μ + 2 ) +。 基乙基）一 5 — (2 —正丙氧 6 -二氫一 7Η —吡唑並〔4 合物及4 一（ 2 —氯乙基）嗎 1 5 Β之步驟製得，呈黃色泡.9〇；Η，7.33;Ν， 〇3;〇.1〇CH2C12計 7.25 ;N，16.14% 本纸張尺度適用中國國家標準（CNS ) A4規格（210X297公釐）~- 292 - (請先閱讀背面之注意事項再填寫本頁) 訂 524805 A7 B7 五、發明説明（290) 〇 (5(CDCl3):l.〇6(3H，t)， 1 · 1 4 ( 3 Η，t )， 1 · 8 8 ( 2 Η，m )， 2 ·〇 0 ( 2 Η，m )， > * 2 . 5 2 ( 4 Η > m )， 3.0〇（4H，m)， 3 · 6 9 ( 4 H，m )， 4 · 1 8 ( 2 H，t )， 4 · 4 2 ( 2 H，t )， 7.〇4(lH，d)， 7 · 1 4 ( 1 H，m )， 7 · 4 5 ( 1 H，m )， 8 . 4 〇（1 H，d )， l〇.85(lH，s)° LRMS:m/z 426 (M+1) +。 製備例1 1 6 2 —〔 2 —（4 一甲基六氣吼啡—1 一基）乙基〕一 5 -（2 -正丙氧苯基）一 3 —正丙基一 2，6 —二氫— 7 Η -吡唑並〔4，3 — d〕嘧啶—7 -酮 由製備例1 2之標題化合物及1 — ( 2 —氯乙基）— 4 —甲基六氫吡哄（Europ. J. Med. Chem.，1 995，处，77 ! )依製備例1 5 B之步驟製得，呈白色泡沬狀（1 7 % ) 本紙張尺度適用中國國家標準（CNS ) A4規格（210X297公釐）-293 - |裝-- (請先閱讀背面之注意事項再填寫本頁) 訂 # 經濟部中央標準局員工消費合作社印製 經濟部中央標準局員工消費合作社印製 524805 A7 B7 五、發明説明（29) 〇 5(CDCl3):l.〇5(3H，t)， 1 · 1 2 ( 3 Η，t )， 1 · 8 6 ( 2 Η，m )， 1 · 9 8 ( 2 Η，m )， 2 · 2 8 ( 3 Η，s )， 2 · 4 4 ( 4 Η，m )， 2 · 5 8 ( 4 Η，m )， 2 · 9 7 ( 4 Η，m )， 4 · 1 7 ( 2 Η，t )， 4 · 3 9 ( 2 Η，t )， 7 ·〇 3 ( 1 Η，d )， 7 · 1 2 ( 1 Η，m )， 7 · 4 4 ( 1 Η，m )， 8 · 4 0 ( 1 Η，d )， l〇.85(lH，s)。 LRMS:m/z 439 (M+1)+。 製備例1 1 7 1 — ( 2 —氯乙基）吡嗤 在氮氣下將1 一溴—2 —氯乙烷（6 · 0ml ，72 m m ◦ 1 )逐滴加入一個在劇烈攪拌中且以冰冷卻而含有 吡唑（5 ·〇g ，7 3 m m〇1 )，碳酸鉀（1〇·〇g ，7 3 m m ο 1 )及丙酮（9 5 m 1 )之混合物裡· 3小 本紙張尺度適用中國國家標準（CNS ) A4規格（210X 297公釐） -294 - (請先閲讀背面之注意事項再填寫本頁)524805 A7 B7 Printed by the Consumer Cooperatives of the Central Standards Bureau of the Ministry of Economic Affairs 5. Description of the invention (289) 2 · 0 〇 (2 Η, m), 2 · 5 2 (4 Η, m), 2 · 8 8 (2 Η, t), 2 · 9 3 (2 Η, t), 3 · 6 2 (4 Η, m),) 4 · 1 9 (2 Η, t), 4 · 7 〇 (2 Η, t), 7 · 〇4 (1Η, d), 7.15 (1Η, m), 7.44 (1Η, m), 8.50 (1Η, d), '10 .65 (1H, s) ° LRMS: m / z 4 2 7 Preparation Example 1 1 5 2 — (2 —morpholine — 4 —phenyl) — 3 —n-propyl-2,, 3 — d] pyrimidin-7-one was prepared from The free base of the titled morpholine hydrochloride of Example 12 was in the form of a hydrazone (24%). Elemental analysis: ，: C, 6 3 16. 2 1. C23H31N: Calculate 値 C, 6 3. 9 3; Η, (Μ + 2) +. Ethyl) a 5-(2-n-propoxy 6-dihydro-7 Η-pyrazolo [4 compound and 4 a (2-chloroethyl) 1 5 B step prepared, a yellow bubble. 9〇; Η, 7.33; Ν, 〇3; 〇.1〇CH2C12 counts 7.25; N, 16.14% This paper size applies to China National Standard (CNS) A4 specification (210X297 mm) ~-292-(Please read first Note on the back, please fill in this page again) Order 524805 A7 B7 V. Description of the invention (290) 〇 (5 (CDCl3): 1.0 (6H, t), 1 · 1 4 (3 Η, t), 1 · 8 8 (2 Η, m), 2 · 〇 0 (2 Η, m), > * 2.5. 2 (4 Η > m), 3.0 0 (4H, m), 3 · 6 9 (4 H , M), 4 · 1 8 (2 H, t), 4 · 4 2 (2 H, t), 7.04 (lH, d), 7 · 1 4 (1 H, m), 7 · 4 5 (1 H, m), 8.4 (1 H, d), 10.85 (1 H, s) ° LRMS: m / z 426 (M + 1) +. Preparation Example 1 1 6 2 — [ 2- (4-Methylhexakiorphin-1-yl) ethyl]-5-(2-n-propoxyphenyl) -3-n-propyl-2,6-dihydro-7 pyrene-pyrazole And [4,3-d] pyrimidin-7-one were prepared from the title compound of Preparation 1 2 and 1-(2 —Chloroethyl) — 4-methylhexahydropyridine (Europ. J. Med. Chem., 1 995, Division, 77!) Was prepared according to the procedure of Preparation 1 5 B, and was white foamy (1 7%) This paper size applies to Chinese National Standard (CNS) A4 specification (210X297mm) -293-| installed-(Please read the precautions on the back before filling this page) Order # Staff Consumer Cooperatives, Central Standards Bureau, Ministry of Economic Affairs Printed by the Consumers' Cooperative of the Central Standards Bureau of the Ministry of Economic Affairs and Printing · 8 6 (2 Η, m), 1 · 9 8 (2 Η, m), 2 · 2 8 (3 Η, s), 2 · 4 4 (4 Η, m), 2 · 5 8 (4 Η , M), 2 · 9 7 (4 Η, m), 4 · 1 7 (2 Η, t), 4 · 3 9 (2 Η, t), 7 · 〇3 (1 Η, d), 7 · 1 2 (1 Η, m), 7 · 4 4 (1 Η, m), 8 · 4 0 (1 Η, d), 10.85 (1H, s). LRMS: m / z 439 (M + 1) +. Preparation Example 1 1 7 1 — (2-chloroethyl) pyridine Under nitrogen, 1 monobromo-2-chloroethane (6.0 ml, 72 mm ◦ 1) was added dropwise to one with vigorous stirring and ice-cold. However, it contains a mixture of pyrazole (5.0 g, 73 mm 〇1), potassium carbonate (10 g, 73 mm ο 1), and acetone (95 m 1) · 3 small paper sizes Applicable to China National Standard (CNS) A4 specification (210X 297 mm) -294-(Please read the precautions on the back before filling this page)

524805 經濟部中央標準局員工消費合作社印製 Α7 Β7 五、發明説明（292) 時後把冷卻浴移開，再於室溫下攪拌3天，然後過濾。將 濾液減壓蒸發，以管柱層析法利用一氯甲院：甲醇（9 7 :3 )爲沖提液於砂膠上純化該蒸發殘餘物而得澄淸油狀 之標題化合物（1 · 6 2 g )。 5 ( C D C 1 3 ) :3.90(2H，m)， 4 · 4 2 ( 2 Η，m )， 6 · 2 3 ( 1 Η，s )， 7 · 6 3 ( 1 Η，s )， 7 · 6 5 ( 1 Η，s )。 L R M S ： m / z 131(M+1)+。 製備例1 1 8 5— (2 —正丙氧苯基）—3 -正丙基一 2 -（2 — 口比D坐一 1—基乙基）一 2，6 —二氫一7H — D比卩坐並〔4 ，3 - d〕嘧啶—7 -酮 由製備例1 2及製備例1 1 7之標題化合物依製備例 15B之步驟製得，呈白色固體（63%)。 5 ( C D C 1 3 ):〇·82(3Η，ΐ)， 1 · 1 〇（3 Η，t )， 1 · 5 6 ( 2 Η，m )， 1 · 9 8 ( 2 Η，m )， 2 · 4 7 ( 2 Η，t )， 4 . 1 6 ( 2 Η，t )， 4 · 6 4 ( 2 Η，m )， 本紙張尺度適用中國國家標準（CNS ) Α4規格（210X297公釐）-295 · (讀先閲讀背面之注意事項再填寫本頁) 、1Τ φ 524805 經濟部中央標率局員工消費合作社印¾ A7 B7 五、發明説明（293) 4.78(2H，m)， 6 · Ο 2 ( 1 Η，s )， 6 · 8 8 ( 1 Η，s )， 7 ·〇 Ο ( 1 Η，d )， 7 ·〇 4 ( 1 Η，m )， 7 · 4 Ο ( 1 Η，m )， 7 · 5 Ο ( 1 Η，m )， 8 · 3 6 ( 1 Η，d )， l〇.58(lH，s)。 L R Μ S ： m / z 407 (M+1)+。 製備例1 1 9 1一（2 —氯乙基）一1，2，3 —三口坐 在一攪拌中且以冰冷卻而由1，2 , 3 —三唑（ 8.4g，121mmol)於甲醇（125ml)中所 形成的溶液裡添加甲氧化鈉（7 · 0 g，1 2 1 m m ο 1 )，接著逐滴添加1 一溴一 2 —氯乙院（l〇.〇m 1 ， 1 2 1 m m ο 1 )。將冷卻浴移開後於室溫下攪拌反應混 合物2天，然後減壓蒸發。令殘餘物在乙酸乙酯（1 2 5 m 1 )及鹽水（1 〇 〇 m 1 )之間分配，把分離出來的有 機相乾燥（M g .S 0 4 ) ’減壓蒸發。殘餘物以管柱層析法 利用二氯甲烷：甲醇（9 6 : 4 )爲沖提液，於矽膠上純 化而得澄淸油狀的標題化合物（2 · 1 9 g )。 5 ( C D C 1 3 ) :3.88(2H，m)， 本紙張尺度適用中國國家標準（CNS ) A4規格（2丨0X297公釐）_ 296 - (請先閱讀背面之注意事項再填寫本頁 訂524805 Printed by the Consumer Cooperatives of the Central Bureau of Standards of the Ministry of Economic Affairs Α7 Β7 V. Description of the invention (292) After that, remove the cooling bath, stir at room temperature for 3 days, and then filter. The filtrate was evaporated under reduced pressure, and the evaporation residue was purified on a sand gel using monochloromethane: methanol (97: 3) as the eluent by column chromatography to obtain the title compound (1 · 6 2 g). 5 (CDC 1 3): 3.90 (2H, m), 4 · 4 2 (2 Η, m), 6 · 2 3 (1 Η, s), 7 · 6 3 (1 Η, s), 7 · 6 5 (1 Η, s). L R M S: m / z 131 (M + 1) +. Production Example 1 1 8 5— (2-n-propoxyphenyl) -3—n-propyl-2— (2—port ratio D—1—ylethyl) —2, 6—dihydro—7H — D [4,3-d] pyrimidin-7-one was prepared from the title compound of Preparation Example 12 and Preparation Example 17 according to the procedure of Preparation Example 15B as a white solid (63%). 5 (CDC 1 3): 〇82 (3Η, ΐ), 1 · 1〇 (3Η, t), 1 · 56 (2Η, m), 1 · 98 (2Η, m), 2 · 4 7 (2 Η, t), 4. 1 6 (2 Η, t), 4 · 6 4 (2 Η, m), this paper size applies Chinese National Standard (CNS) Α4 specification (210X297 mm)- 295 (Read the precautions on the back before filling this page), 1T φ 524805 Printed by the Consumer Cooperatives of the Central Standards Bureau, Ministry of Economic Affairs ¾ A7 B7 V. Invention Description (293) 4.78 (2H, m), 6 · Ο 2 (1 Η, s), 6 · 8 8 (1 Η, s), 7 · 〇 (1 Η, d), 7 · 〇 4 (1 Η, m), 7 · 4 〇 (1 Η, m) , 7 · 5 Ο (1 Η, m), 8 · 3 6 (1 Η, d), 10.58 (1H, s). L R M S: m / z 407 (M + 1) +. Preparation Example 1 1 9 1- (2-chloroethyl) -1,2,3-3-three sitting in a stirring and cooling with ice while 1,2,3-triazole (8.4g, 121mmol) in methanol ( 125 ml) was added to the solution formed by sodium methoxide (7.0 g, 12 1 mm ο 1), followed by dropwise addition of 1-bromo-2 -chloroethane (10. 0 m 1, 1 2 1 mm ο 1). After removing the cooling bath, the reaction mixture was stirred at room temperature for 2 days, and then evaporated under reduced pressure. The residue was partitioned between ethyl acetate (125 m 1) and brine (1000 m 1), and the separated organic phase was dried (M g. S 0 4) 'and evaporated under reduced pressure. The residue was purified by column chromatography using dichloromethane: methanol (96: 4) as the eluent and purified on silica gel to obtain the title compound (2.19 g) as a clear oil. 5 (C D C 1 3): 3.88 (2H, m), this paper size applies Chinese National Standard (CNS) A4 specification (2 丨 0X297 mm) _ 296-(Please read the precautions on the back before filling this page. Order

524805 A7 B7 五、發明説明（294) 4 · 6 8 ( 2 Η，m )， 7 · 5 〇（1 Η，s )， 7 · 6 〇（1 Η，s )。 LRMS:m/z 132(M+1)+。 製備例1 2〇 5 -（2 —正丙氧苯基）一 3 -正丙基一 2 —〔2 -(1 ，2，3 —三唑一1—基）乙基〕一 2，6 —二氫一 7 Η -吡唑並〔4，3 - d〕嘧啶一 7 —酮 由製備例1 2及製備例1 1 9之標題化合物依製備例 15B之步驟製得，呈白色固體（60%)。 (讀先閱讀背面之注意事項再填寫本頁)524805 A7 B7 V. Description of the invention (294) 4 · 6 8 (2 Η, m), 7 · 5 〇 (1 Η, s), 7 · 6 〇 (1 Η, s). LRMS: m / z 132 (M + 1) +. Production Example 1 2 05- (2-n-propoxyphenyl) -3-n-propyl-2- [2- (1,2,3-triazole-1-yl) ethyl] -2,6- Dihydro-7 pyrene-pyrazolo [4,3-d] pyrimidin-7-one was prepared from the title compound of Preparation Example 12 and Preparation Example 19 according to the procedure of Preparation Example 15B, as a white solid (60% ). (Read the precautions on the back before filling this page)

Xu 經濟部中央標準局員工消費合作社印製 iti—-244577778 tmmttttdooms d ^hhhhhhhh · Η Η H 1322222217111 /IV xi\ /mV /IV /(V /(V /IV j /—V κί\ /~\ D706682404068 C059507000443 Η 3 2 8 〇 m Η 2Xu Printed by the Consumer Cooperative of the Central Standards Bureau of the Ministry of Economic Affairs iti—-244577778 tmmttttdooms d ^ hhhhhhhh C059507000443 Η 3 2 8 〇m Η 2

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本紙張尺度適用中國國家標準（CNS ) Α4規格（210X 297公釐）-297 - 524805 經濟部中央標準局員工消費合作社印製 A7 _五、發明説明（295) 1〇·96 (1H，s)。 L R M S ： m / z 4〇8(M+1)+。 製備例1 2 1 1— (2 —氯乙基）—l ，2，4 —三唑 由1 ，2，4 一三唑及l —溴一 2 —氯乙烷依製備例 1 1 7之步驟製得，呈澄淸油狀物（2 2 % )。 5 ( C D C 1 3 ) :3.79(2H，m)， 4 . 1 8 ( 2 Η，m )， 7.84(1H，S)， 8 · 0 4 ( 1 Η，s )。 製備例1 2 2 5 — (2 -正丙氧苯基）—3 —正丙基—2 -〔2 — (1 ’ 2，4 一三卩坐一 1—基）乙基〕—2 ’ 6 —二氫— 7 Η —吡唑並〔4，3 — d〕嘧啶—7 —酮 由製備例1 2及製備例1 2 1之標題化合物依製備例 1 5 B之步驟製得，呈白色泡沬狀（3 2 % )。 ^ ( C D C 1 3 ):〇·8 8* (3H，t)， 1 · 1 1 ( 3 Η，t )， 1 · 5 8 ( 2 Η，m )， 1.98(2H，m)， 2 · 6 0 ( 2 H，t )， 4 · 1 5 ( 2 H，t )， 本紙張尺度適用中國國家標準（CNS ) A4規格（21 OX 297公釐）-298 - (請先閲讀背面之注意事項再填寫本頁) 衣This paper size applies Chinese National Standard (CNS) A4 specification (210X 297 mm) -297-524805 Printed by the Consumer Cooperatives of the Central Standards Bureau of the Ministry of Economic Affairs A7 _V. Description of the invention (295) 1 · 96 (1H, s) . L R M S: m / z 408 (M + 1) +. Preparation Example 1 2 1 1— (2-Chloroethyl) —1,2,4-triazole from 1,2,4-triazole and 1-bromo-2-chloroethane according to the procedure of Preparation Example 1 17 Obtained as a clear oil (22%). 5 (C D C 1 3): 3.79 (2H, m), 4.1 8 (2 Η, m), 7.84 (1H, S), 8 · 0 4 (1 Η, s). Production Example 1 2 2 5 — (2 -n-propoxyphenyl) — 3 —n-propyl — 2 — [2 — (1 ′ 2,4—triamidine—1—yl) ethyl] -2 ′ 6 —Dihydro— 7 hydrazone —pyrazolo [4,3 — d] pyrimidin-7 —one was prepared from the title compound of Preparation Example 12 and Preparation Example 21 according to the procedure of Preparation Example 5 B, and showed a white foam. Cricket-like (32%). ^ (CDC 1 3): 0.88 * (3H, t), 1 · 1 1 (3 Η, t), 1 · 5 8 (2 Η, m), 1.98 (2H, m), 2 · 6 0 (2 H, t), 4 · 1 5 (2 H, t), this paper size applies Chinese National Standard (CNS) A4 specification (21 OX 297 mm) -298-(Please read the precautions on the back before (Fill in this page)

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524805 A7 _ B7 五、發明説明（296) 4 · 6 8 ( 2 Η，t )， 4 · 8 8 ( 2 Η，t )， 7 · 〇 〇（1 Η，d ) ’ 7 · 0 6 ( 1 Η，m )， 7 · 4 〇（1 Η，m )， 7 · 6 8 ( 1 Η，s )， 7 · 9 2 ( 1 Η，s )， 8 · 3 2 ( 1 Η，d )， l〇.90(lH，s)° L R M S ： m / z 408 (M+1)+〇 (請先閱讀背面之注意事項再填寫本頁)524805 A7 _ B7 V. Description of the invention (296) 4 · 6 8 (2 Η, t), 4 · 8 8 (2 Η, t), 7 · 〇〇 (1 Η, d) '7 · 0 6 (1 Η, m), 7 · 4 0 (1 Η, m), 7 · 6 8 (1 Η, s), 7 · 9 2 (1 Η, s), 8 · 3 2 (1 Η, d), l 〇.90 (lH, s) ° LRMS: m / z 408 (M + 1) + 〇 (Please read the precautions on the back before filling this page)

、1T 經濟部中央標準局員工消費合作社印製 製備例1 2 3 2 - (2 -硝苯基）—5 -（2 —正丙氧苯基）一 3 一正丙基—2，6 —二氫—7H —吼哩並〔4，3 — d〕 嘧啶一 7 —酮 由製備例1 2之標題化合物及2 -氟硝基苯依製備例 1 5 Β 之 步 驟 製得 ， 呈黃 i色粉末（6 0 % )。 5 (c D C 1 3 ) ： 0 · 9 0 ( 3 Η，t )， 1 • 0 7 ( 3 Η， t )， 1 .7 6 ( 2 Η， m )， 1 .9 9 ( 2 Η， m )， 2 .8 4 ( 2 Η， t )， 4 .1 5 ( 2 Η， t )， 7 .0 1 ( 1 Η ， d )， 本纸張尺度適用中國國家標準（CNS ) A4規格（210Χ297公釐）-299 - 524805 A7 ____B7__ 五、發明説明（297) 7 · 1 0 ( ί Η，t )， 7 · 4 3 ( 1 Η，t )， 7 · 5 8 ( 1 Η，d )， 7 · 7 0 ( 1 Η，t )， 7 · 7 8 ( 1 Η，t )， 8 · 1 6 ( 1 Η，d )， 8 · 4 2 ( 1 Η，m )， 1〇.93(1H，s) ο LRMS:m/z 434 (M+l)+。 製備例1 2 4 2 -（4 一硝苯基）一 5 -（2 —正丙氧苯基）一 3 一正丙基一 2，6 -二氫—7H —吡唑並〔4，3 — d〕 嘧陡—7 -酮 由製備例1 2之標題化合物及4 -氟硝基苯依製備例 15B之步驟製得，呈黃色固體（72%)。 5(CDCl3):〇.96(3H，t)， (請先閱讀背面之注意事項再填寫本頁) ▼ -訂-, 1T Printed by the Consumer Standards Cooperative of the Central Bureau of Standards of the Ministry of Economic Affairs 1 2 3 2-(2 -Nitrophenyl) -5-(2 -N-propoxyphenyl) -3 -N-propyl-2,6 -2 Hydrogen — 7H — hydrazine [4, 3 — d] pyrimidine — 7 — ketone was prepared from the title compound of Preparation Example 12 and 2-fluoronitrobenzene according to the procedure of Preparation Example 15B, which was a yellow i-colored powder. (60%). 5 (c DC 1 3): 0 · 9 0 (3 Η, t), 1 • 0 7 (3 Η, t), 1. 7 6 (2 Η, m), 1. 9 9 (2 Η, m ), 2 .8 4 (2 Η, t), 4.1 .5 (2 Η, t), 7.0 .1 (1 Η, d), this paper size applies the Chinese National Standard (CNS) A4 specification (210 × 297 (Mm) -299-524805 A7 ____B7__ V. Description of the invention (297) 7 · 10 (ί Η, t), 7 · 4 3 (1 Η, t), 7 · 5 8 (1 Η, d), 7 · 7 0 (1 Η, t), 7 · 7 8 (1 Η, t), 8 · 1 6 (1 Η, d), 8 · 4 2 (1 Η, m), 10.93 (1H, s) ο LRMS: m / z 434 (M + l) +. Preparation Example 1 2 4 2-(4 mononitrophenyl) -5 (2-n-propoxyphenyl) -3 3-n-propyl-2,6-dihydro-7H-pyrazolo [4,3 — d] Pyridox-7-one was prepared from the title compound of Preparation Example 12 and 4-fluoronitrobenzene according to the procedure of Preparation Example 15B, and showed a yellow solid (72%). 5 (CDCl3): 0.96 (3H, t), (Please read the precautions on the back before filling this page) ▼ -Order-

經濟部中央標準局員工消費合作社印製 \)y N)y \)y X)/ \)/ \]y tm0 t t d t Η Η Η Η Η Η H 3 2 2 2 2 1 1 VV /(\v r\ /l\ /IV /V xf\ 4 0 2 2 0 8 8 lx 00 o r~I CX3 ······· 1 1 2 3 4 7 7 本紙張尺度適用中國國家標準（CNS ) A4規格（210X 297公釐）_ 3〇〇 - 經濟部中央標準局員工消費合作社印製 524805 A7 B7 五、發明説明（298) 7 · 4 9 ( 1 Η，t )， 7 · 8 4 ( 2 Η，d .)， 8 · 4 5 ( 3 Η，m )， ll.〇3(lH，s)。 LRMS:m/z 434 (M+1)+。 製備例1 2 5 5-（2-正丙氧苯基）一3-正丙基一2-嘧啶— 2 -基一 2，6 — 二氫一 7H —吡唑並〔4，3 — d〕嘧 啶一 7 -酮 由製備例1 2之標題化合物及2 -氯嘧啶依製備例1 5B之步驟製得，呈白色固體（26%)。 5(CDCl3):l.〇〇（3H，t)， 1.17(3H，t)， 1 · 8 〇（2 Η，m )， 2 ·〇 1 ( 2 Η，m )， 3 · 4 8 ( 2 Η，t )， 4 . 1 9 ( 2 Η，t )， 7 ·〇 5 ( 1 Η，d )， 7 · 1 7 ( 1 Η，m )， 7 · 4 〇（1 Η，m ) ， · 7 · 4 6 ( 1 Η，m )， 8 · 5 〇（1 Η，d )， 8 · 9 2 ( 2 Η，d )， 本紙張尺度適用中國國家標準（CNS ) Α4規格（21〇'〆297公釐）-301 - (讀先閲讀背面之注意事項再填寫本頁)Printed by the Consumer Cooperatives of the Central Bureau of Standards of the Ministry of Economic Affairs \) y N) y \) y X) / \) / \] y tm0 ttdt Η Η Η Η Η Η H 3 2 2 2 2 1 1 VV / (\ vr \ / l \ / IV / V xf \ 4 0 2 2 0 8 8 lx 00 or ~ I CX3 ······· 1 1 2 3 4 7 7 This paper size applies to China National Standard (CNS) A4 specifications (210X 297 mm) _ 300-Printed by the Consumer Cooperatives of the Central Standards Bureau of the Ministry of Economic Affairs 524805 A7 B7 V. Description of the invention (298) 7 · 4 9 (1 Η, t), 7 · 8 4 (2 Η, d. ), 8 · 4 5 (3 Η, m), ll. 03 (lH, s). LRMS: m / z 434 (M + 1) +. Preparation Example 1 2 5 5- (2-n-propoxybenzene ) -3-n-propyl-2-pyrimidin-2-yl-2,6-dihydro-7H-pyrazolo [4,3-d] pyrimidin-7-one from the title compound of Preparation 12 and 2-Chloropyrimidine was prepared according to the procedure of Preparation 5B as a white solid (26%). 5 (CDCl3): 1.0 (3H, t), 1.17 (3H, t), 1. 8 (2 Η, m), 2 · 〇1 (2 Η, m), 3 · 4 8 (2 Η, t), 4. 19 (2 Η, t), 7 · 〇5 (1 Η, d), 7 · 1 7 (1 Η, m), 7 · 4 〇 (1 Η, m), · 7 · 4 6 (1 Η, m), 8 · 5 〇 (1 Η, d), 8 · 9 2 (2 Η, d), this paper size applies Chinese National Standard (CNS) A4 specification (21〇 '297 mm) -301-(Read the precautions on the back before filling in this page)

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524805 A7 B7 — —— ____五、發明説明（299) 10.98(lH，s) 〇 LRMS:m/z 391 (M+l) +。 製備例1 2 6 2 —環丁甲基一5 —（2 —乙氧苯基）一 3 —正丙基 一 2，6 —二氫一7H — D比哩並〔4，3 — d〕&密 u定一 7 一酮 由製備例1 4之標題化合物及甲烷磺醯氧甲基環丁院 (J. Chem. Soc. Perkin II，1981，970 )依製備例 1 5 C 之 步驟製得（2 5 % )。 元素分析實測値：C，6 8 · 6 2 ; Η，7 · 1 3 ; N， 15 · 21。C21H26N4〇2計算値 C，68 · 83 ； Η ，7.15 ;N， 15.29%。 經濟部中央標準局員工消費合作社印製 3 ΗΗΗΗΗΗΗΗΗ1 1362341111( ο /ι\ /IV Γν Γν /IV /{\ /IV /ι\ 4- D8878032408 C58 ο 830144 · /—\ ·········. C—〕 51122477781 Η 3 κί\ 5 〇 mmsmdmmd \1/ \)/ Η524805 A7 B7 — —— ____ V. Description of the invention (299) 10.98 (lH, s) 〇 LRMS: m / z 391 (M + l) +. Production Example 1 2 6 2 —Cyclobutylmethyl—5— (2-ethoxyphenyl) —3—n-propyl—2,6—dihydro—7H—D ratio mile [4,3 — d] & dense定 定 -7 ketone was prepared from the title compound of Preparation 14 and methanesulfonylmethylcyclobutane (J. Chem. Soc. Perkin II, 1981, 970) according to the procedure of Preparation 5 C (2 5%). Elemental analysis: 値: C, 6 8 · 6 2; Η, 7 · 1 3; N, 15 · 21. C21H26N4 02 calculates 値 C, 68 · 83; Η, 7.15; N, 15.29%. Printed by the Consumer Cooperatives of the Central Standards Bureau of the Ministry of Economic Affairs 3 ΗΗΗΗΗΗΗΗΗ1 1362341111 (ο / ι \ / IV Γν Γν / IV / {\ / IV / ι \ 4- D8878032408 C58 ο 830144 · / — \ ········ ·. C—] 51122477781 Η 3 κί \ 5 〇mmsmdmmd \ 1 / \) / Η

S (請先閲讀背面之注意事項再填寫本頁)S (Please read the notes on the back before filling this page)

本紙張尺度適用中國國家標準（CNS ) A4規格（21 OX297公釐）-302 - 524805 A7 B7 經濟部中央標準局員工消費合作社印製 五、發明説明（300) LRMS :m/z 367 (M+l)+。 製備例1 2 7 2—環丁甲基一5—(2—正丙氧苯基）一3—正丙 基一 2，6 —二氫一 7H —吡唑並〔4，3 - d〕嘧啶一 7 -酮 由製備例1 2之標題化合物及甲烷磺醯氧甲基環丁烷 (J· Chem. Soc. Perkin II，1981，970 )依製備例 15C之步驟製得，呈白色固體（23%)。 5 ( C D C 1 a ) :l.〇5(3H，t)， 1 · 1 2 ( 3 Η，t )， 1.84 — 2.06 (l〇H，m)， 2 · 9 8 ( 3 Η，m )， 4 · 1 7 ( 2 Η，t )， 4 · 3 2 ( 2 Η，d )， 7 · 0 4 ( 1 Η，d )， 7 · 1 2 ( 1 Η，m )， 7 · 4 4 ( 1 Η，m )， 8 · 3 9 ( 1 Η，d )，l〇.7〇（lH，s)。 L R M S ： m / z 381(M+1)+。 製備例1 2 8 2—(2—甲氧乙氧）苄酸甲酯 本紙張尺度適用中國國家標準（CNS ) Α4規格（210X297公釐）-303 - (請先閱讀背面之注意事項再填寫本頁) •^^衣·This paper size applies to Chinese National Standard (CNS) A4 (21 OX297 mm) -302-524805 A7 B7 Printed by the Consumer Cooperatives of the Central Standards Bureau of the Ministry of Economic Affairs 5. Description of the invention (300) LRMS: m / z 367 (M + l) +. Production Example 1 2 7 2-cyclobutylmethyl-5- (2-n-propoxyphenyl) -3-n-propyl-2,6-dihydro-7H-pyrazolo [4,3-d] pyrimidine-7 -Ketone was prepared from the title compound of Preparation Example 12 and methanesulfonyloxymethylcyclobutane (J. Chem. Soc. Perkin II, 1981, 970) according to the procedure of Preparation Example 15C, as a white solid (23%) . 5 (CDC 1 a): 1.05 (3H, t), 1 · 1 2 (3 Η, t), 1.84-2.06 (10 ，, m), 2 · 9 8 (3 Η, m), 4 · 1 7 (2 Η, t), 4 · 3 2 (2 Η, d), 7 · 0 4 (1 Η, d), 7 · 1 2 (1 Η, m), 7 · 4 4 (1 Η, m), 8 · 39 (1 Η, d), 10.7 (1H, s). L R M S: m / z 381 (M + 1) +. Preparation Example 1 2 8 2— (2-Methoxyethoxy) methyl benzate This paper is sized for China National Standard (CNS) A4 (210X297 mm) -303-(Please read the precautions on the back before filling in this Page) • ^^ 衣 ·

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524805 經濟部中央榡準局員工消費合作社印製 A7 B7 五、發明説明（3〇1) 將偶氮二羧酸二乙酯（7 · Og，40 · 4mm〇 1 )逐滴加入柳酸甲酯（5 · 1 g ，3 3 · 5 m m〇1 )， 2-甲氧乙醇（2 · 6g ，34 · lmmo 1)與三苯膦 (1 0 · 6 g，4 0 · 4 m m ο 1 )的攪拌溶液裡，再於 室溫下攪拌1 8小時，然後減壓蒸發。殘餘物以乙醚碾製 ，所得混合物經過濾後，將濾液減壓蒸發，再將殘餘物以 管柱層析法利用戊烷：乙醚（1 〇 〇 : 〇至8 〇 : 2〇） 之沖提梯度於矽膠上純化而得無色油狀標題化合物（ 4 · 8 〇 g，6 8 % )。 5(CDC13):3.51(3H，s)， 3 · 8 5 ( 2 Η，t )， 3 · 9 2 ( 3 Η，s )， 4 · 2 3 ( 2 Η，t )， 7.03(2H，m)， 7 · 4 8 ( 1 Η，m )， 7 · 8 3 ( 1 Η，d )。 製備例1 2 9 2 — (2 —甲氧乙氧）苄酸 將製備例1 2 8標題化合物（4 · 8 g，2 2 · 8 m m ο 1 )及2 Μ氫氧化鈉水溶液（2 5 m 1 ，5 0 m m ο 1 )之混合物在室溫下攪拌4小時，再用乙醚洗過，把所 得水溶液以1 Μ氫氯酸酸化至ρ η 3，接著以二氯甲烷（ 3 X 5 0 m 1 )萃取。合倂的萃取液乾燥（M g s〇4 )後 (請先閱讀背面之注意事項再填寫本頁)524805 A7 B7 printed by the Consumer Cooperatives of the Central Government Bureau of the Ministry of Economic Affairs V. Description of the invention (30.1) Diethyl azodicarboxylate (7. Og, 40. 4mm) was added dropwise to methyl salicylate (5 · 1 g, 3 · 3 · 5 mm〇1), 2-methoxyethanol (2 · 6g, 34 · lmmo 1) and triphenylphosphine (1 0 · 6 g, 4 · 4 · 4 mm ο 1) The solution was stirred, stirred at room temperature for 18 hours, and then evaporated under reduced pressure. The residue was triturated with diethyl ether. After the resulting mixture was filtered, the filtrate was evaporated under reduced pressure, and the residue was subjected to column chromatography using pentane: diethyl ether (100: 0 to 80: 20). The gradient was purified on silica gel to give the title compound (4.80 g, 68%) as a colorless oil. 5 (CDC13): 3.51 (3H, s), 3 · 8 5 (2 Η, t), 3 · 9 2 (3 Η, s), 4 · 2 3 (2 Η, t), 7.03 (2H, m ), 7 · 4 8 (1 Η, m), 7 · 8 3 (1 Η, d). Preparation Example 1 2 9 2 — (2-methoxyethoxy) benzoic acid The title compound of Preparation Example 1 2 (4 · 8 g, 2 2 · 8 mm ο 1) and 2 M aqueous sodium hydroxide solution (2 5 m 1,50 mm ο 1) of the mixture was stirred at room temperature for 4 hours, and then washed with ether, the resulting aqueous solution was acidified with 1 M hydrochloric acid to ρ η 3, followed by dichloromethane (3 X 50 m 1) Extraction. After the combined extract is dried (M g s〇4) (Please read the precautions on the back before filling this page)

本紙張尺度適用中國國家標準（CNS ) A4規格（210X 297公釐） -304- 524805 經濟部中央標準局員工消費合作社印製 A7 B7 五、發明説明（3〇2) 減壓蒸發而得油狀標題化合物（4 · 1 6 g，9 3 % )。 5(CDC13):3.5〇（3H，s)， 3 · 8 6 ( 2 Η，t )， 4 · 4 1 ( 2 Η，t )， 7.08(lH，d)， 7.19(lH，m)， 7.58(lH，m)， 8 · 2 2 ( 1 H，d )。 製備例1 3〇 3 —乙基一4 一硝基一2 —（吡啶一 2 —基）甲基吡 唑—5 —甲醯胺 在室溫下將製備例6標題化合物（2 0 · 〇 g， 1 0 9 m m ο 1 ) ，2 —氯甲基吡啶鹽酸鹽（17 .9g ，109mm〇l)，碳酸絶（74.7g，222 m m ο 1 )及二甲基甲醯胺（1 2 〇 m 1 )之混合物攪拌 1 8小時，然後減壓蒸發。令殘餘物在二氯甲烷（1〇〇 m 1 )和水（1 〇 〇 m 1 )之間分配，把水相分離出來後 用二氯甲烷（3 X 1 〇 〇 m 1 )萃取。將有機相加入萃取 液裡，再把合倂的二氯甲烷溶液乾燥（M g S〇4 )，減壓 蒸發後以二氯甲烷：甲醇對蒸發殘餘物進行結晶而得到標 題化合物之1一異構物，即3 —乙基一 4 —硝基一 1 一（ 吡啶一 2 —基）甲基吡唑一 5 —甲醯胺。 將母液減壓蒸發，再以管柱層析法利用二氯甲烷：甲 本紙張尺度適用中國國家標準（CNS ) A4規格（210X297公釐）-305 - (讀先閱讀背面之注意事項再填寫本頁) 衣.This paper size applies to Chinese National Standard (CNS) A4 (210X 297 mm) -304- 524805 Printed by the Consumer Cooperatives of the Central Standards Bureau of the Ministry of Economic Affairs A7 B7 V. Description of the invention (30.2) Evaporated under reduced pressure to obtain an oily state The title compound (4.16 g, 93%). 5 (CDC13): 3.50 (3H, s), 3.86 (2 Η, t), 4.4.1 (2 Η, t), 7.08 (lH, d), 7.19 (lH, m), 7.58 (lH, m), 8 · 2 2 (1 H, d). Preparation Example 1 3〇3-ethyl-4 mononitro-2- (pyridine-2-yl) methylpyrazole-5-formamidine The title compound of Preparation 6 (20 g) was prepared at room temperature. , 10 9 mm ο 1), 2-chloromethylpyridine hydrochloride (17.9 g, 109 mm), carbonic acid (74.7 g, 222 mm ο 1), and dimethylformamide (1 2 〇 The mixture of m 1) was stirred for 18 hours and then evaporated under reduced pressure. The residue was partitioned between dichloromethane (100 m 1) and water (100 m 1), the aqueous phase was separated and extracted with dichloromethane (3 × 100 m 1). The organic phase was added to the extract, and the combined dichloromethane solution was dried (Mg S04). After evaporation under reduced pressure, the evaporation residue was crystallized from dichloromethane: methanol to obtain the title compound. Structure, that is, 3-ethyl-4-nitro-1, 1- (pyridine-2-yl) methylpyrazole-5, methylamine. Evaporate the mother liquor under reduced pressure, and then use dichloromethane by column chromatography: A paper size applies the Chinese National Standard (CNS) A4 specification (210X297 mm) -305-(Read the precautions on the back before filling in this Page) clothing.

、1T 524805 A7B7 經濟部中央標隼局員工消費合作社印^ 五、發明説明（3〇3) 醇（1 0 0 : 0至9 5 : 5 )爲沖提梯度’於矽膠上純化 而得白色固體之標題化合物。（17 · 36g，58%) 〇(5(CDCl3):1.16(3H，t)， 3 ·〇 6 ( 2 Η，Q )， 5 · 4 8 ( 2 Η，s )， 5 · 8 8 ( 1 Η，s )， 7 · 1 9 ( 1 Η，d )， 7 . 2 7 ( 2 Η，m )， 7 · 7 〇（1 Η，m )， 8 · 5 7 ( 1 Η，d )。 製備例1 3 1 4 一胺基一3 —乙基—2—(吡啶—2 —基）甲基吡 唑一 5 —甲醯胺 由製備例1 3 0之標題化合物依標題化合物7之步驟 製得，但氫化反應只進行4小時。結果呈白色固體（8 7 % )。 5(CDCl3):l.〇3(3H，t)， 2 . 5 3 ( 2 Η， Q )， 4 · 0 〇 ( 2 Η， s )， 5 . 2 2 ( 1 Η， s )， 5 . 3 6 ( 2 Η， * s )， 6 . 6 〇 ( 1 Η ， ，s )， 本紙張尺度適用中國國家標率（CNS ) Α4規格（210Χ 297公釐）-306 - (讀先閱讀背面之注意事項再填寫本頁) 衣 '、 1T 524805 A7B7 Printed by the Consumer Cooperatives of the Central Bureau of Standards of the Ministry of Economic Affairs ^ V. Description of the invention (303) Alcohol (100: 0 to 9 5: 5) is a white solid obtained by purification on silica gel for gradient extraction Title compound. (17.36g, 58%) 〇 (5 (CDCl3): 1.16 (3H, t), 3.〇6 (2 Η, Q), 5 · 4 8 (2 Η, s), 5 · 8 8 (1 Η, s), 7 · 19 (1 Η, d), 7. 2 7 (2 Η, m), 7 · 7 〇 (1 Η, m), 8 · 5 7 (1 Η, d). Preparation Example 1 3 1 4 Monoamino-3 -ethyl-2- (pyridine-2-yl) methylpyrazole-5-formamidine was prepared from the title compound of Preparation Example 1 3 according to the procedure for the title compound 7 , But the hydrogenation reaction only took 4 hours. The result was a white solid (87%). 5 (CDCl3): 1.03 (3H, t), 2.53 (2 Η, Q), 4.0 〇 ( 2 Η, s), 5. 2 2 (1 Η, s), 5. 3 6 (2 Η, * s), 6. 6 〇 (1 Η,, s), this paper scale applies Chinese national standard ( CNS) Α4 size (210 × 297 mm) -306-(Read the precautions on the back before filling in this page) Clothing ''

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524805 經濟部中央標準局員工消費合作社印製 A7 B7 五、發明説明（3〇4) 6 · 8 1 ( 1 Η，d )， 7 · 2 Ο ( 1 Η，m )， 7 · 6 2 ( 1 Η，m )， 8 · 5 7 ( 1 Η，d )。 LRMS:m/z 246 (M+1)+。 製備例1 3 2 3 —乙基一 4 —〔 2 — (2 —甲氧乙氧）苄醯胺基〕 一 2 —(吡啶一 2 —基）甲基吡唑一 5 —甲醯胺 將草醯氯（3 · 05g，24mmo 1)逐滴加入含 有製備例1 2 9標題化合物（2 · 3 5 g，1 2 m m ο 1 )，二甲基甲醯胺（5滴）及二氯甲烷（40ml)的攪 拌溶液裡，再於室溫下攪拌1小時，然後減壓蒸發。 把該殘餘粗製醯氯的二氯甲烷（2 0 m 1 )溶液逐滴 加入一攪拌中而由製備例1 3 1標題化合物（2 · 4 5 g ’ lOmmo 1)於三乙胺（5 ·〇5g ， 5〇mmo 1 )與二氯甲烷（2 0 m 1 )之混合物中所形成的懸浮液裡 。在室溫下攪拌此反應混合物1 8小時，然後減壓蒸發。 令蒸發殘餘物在乙酸乙酯（5 0m 1 )及水（2 0 m 1 ) 之間分配，然後把有機相依序以1 Μ檸檬酸水溶液（2 0 ml) ，2 Μ氫氧化鈉水溶液（2 0 m 1 )及鹽水（2〇 m 1 )洗過’乾燥（M g S〇4 )後減壓蒸發。粗產物以管 柱層析法利用二氯甲烷：甲醇（1 0 〇 : 〇至9 3 : 7 ) 爲沖提梯度而得到泡沬狀的標題化合物（3 . 1 9 g， 本紙張尺度適用中國國家標準（CNS ) Α4規格（210Χ 297公釐）-307 - T— (請先閱讀背面之注意事項再填寫本頁)524805 Printed by the Consumer Cooperative of the Central Bureau of Standards of the Ministry of Economic Affairs A7 B7 V. Description of the invention (30) 6 · 8 1 (1 Η, d), 7 · 2 〇 (1 Η, m), 7 · 6 2 (1 Η, m), 8 · 5 7 (1 Η, d). LRMS: m / z 246 (M + 1) +. Preparation Example 1 3 2 3 -Ethyl-4-[2-(2-methoxyethoxy) benzylamido]-2-(pyridine-2 -yl) methylpyrazole-5 -formamide Chlorine (3. 05 g, 24 mmo 1) was added dropwise to contain the title compound of Preparation Example 1 2 9 (2. 3 5 g, 12 mm 1), dimethylformamide (5 drops), and dichloromethane ( 40 ml) of the stirred solution, stirred at room temperature for 1 hour, and then evaporated under reduced pressure. A solution of the residual crude chloroform in dichloromethane (20 m 1) was added dropwise to a stirring solution from the title compound of Preparation Example 31 (2.45 g '10 mmo 1) in triethylamine (5.0 5 g of a suspension formed in a mixture of 50 mmo 1) and dichloromethane (20 m 1). The reaction mixture was stirred at room temperature for 18 hours and then evaporated under reduced pressure. The evaporation residue was partitioned between ethyl acetate (50 m 1) and water (20 m 1), and the organic phase was sequentially divided into 1 M aqueous citric acid solution (20 ml) and 2 M aqueous sodium hydroxide solution (2 After washing with 0 m 1) and brine (20 m 1) and drying (M g S04), it was evaporated under reduced pressure. The crude product was purified by column chromatography using dichloromethane: methanol (100: 0 to 9 3: 7) as a gradient to obtain the title compound (3.19 g) in the form of foam. National Standard (CNS) Α4 Specification (210 × 297 mm) -307-T— (Please read the precautions on the back before filling this page)

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524805 經濟部中央標隼局員工消費合作社印製 kl B7 五、發明説明（3〇$ 7 5%)。 5(CDCl3)：l.〇8(3H^t)^ 2 · 8 4 ( 2 Η，q )， 3 · 3 6 ( 3 Η，s )， 3 · 9 4 ( 2 Η，t )， 4 · 4 〇（2 Η，t )， 5 · 2 7 ( 1 Η，s )， 5 · 4 8 ( 2 Η，s )， 6 · 7 3 ( 1 Η，s )， 6 · 9 2 ( 1 Η，d )， 7 ·〇 7 ( 2 Η，m )， 7 · 2 2 ( 1 Η，m )， 7 · 4 5 ( 1 Η，m )， 7 · 6 5 ( 1 Η，. m )， 8 · 2 3 ( 1 Η，d )， 8 · 5 9 ( 1 Η，d )， 1 〇· 3 4 ( 1 Η，s )。 L R M S ： m / z 424(M+1) +。 製備例1 3 3 3 —乙基一5 —〔2— (2 —甲氧乙氧）苯基〕一2 一（吡啶—2 —基）甲基一 2，6 —二氫—7H —吡唑並 〔4，3 — d〕嚼π定一 7 —酮 將第三丁氧化鉀（1 ._12g，lOmmo 1)加一 本紙張尺度適用中國國家標準（CNS ) A4規格（210Χ 297公釐） - 308 - (請先閱讀背面之注意事項再填寫本頁)524805 Printed by the Consumers' Cooperative of the Central Bureau of Standards of the Ministry of Economic Affairs Kl B7 V. Description of Invention (30 $ 7 5%). 5 (CDCl3): 1.08 (3H ^ t) ^ 2 · 8 4 (2 Η, q), 3 · 3 6 (3 Η, s), 3 · 9 4 (2 Η, t), 4 · 4 0 (2 Η, t), 5 · 2 7 (1 Η, s), 5 · 4 8 (2 Η, s), 6 · 7 3 (1 Η, s), 6 · 9 2 (1 Η, d), 7 · 〇7 (2 Η, m), 7 · 2 2 (1 Η, m), 7 · 4 5 (1 Η, m), 7 · 6 5 (1 Η,. m), 8 · 2 3 (1 Η, d), 8 · 5 9 (1 Η, d), 1 0.3 · 4 (1 Η, s). L R M S: m / z 424 (M + 1) +. Production Example 1 3 3 3 —Ethyl-5— [2- (2-methoxyethoxy) phenyl] -2 (pyridin-2-yl) methyl-1,6-dihydro-7H—pyrazole And [4,3 — d] chelate π- 7-one, the third potassium butoxide (1 ._12g, 10mmo 1) plus a paper size applicable to the Chinese National Standard (CNS) A4 specifications (210 × 297 mm)- 308-(Please read the notes on the back before filling this page)

524805 經濟部中央標準局員工消費合作社印製 A7 B7 五、發明説明（3〇$ 攪拌中而含有製備例1 3 2標題化合物（3 · 1 5 g， 7 · 4 5 m m ο 1 )與正丙醇（4 0 m 1 )的溶液裡，經 加熱迴流6小時後冷卻。接著添加乙酸乙酯（6 0 m 1 ) ，再將所得混合物依序以1 Μ檸檬酸水溶液（2 5 m 1 ) 及鹽水（2 5 m 1 )洗過，經乾燥（M g S〇4 )後減壓蒸 發。殘餘物以管柱層析法利用二氯甲烷：甲醇（1 0 0 : 0至9 5 : 5 )爲沖提梯度於矽膠上純化而得到標題化合 物（2.17g，72%)。 5(CDCl3):1.29(3H，t)， 3 · 0 〇（2 Η，q )， 3 · 5 7 ( 3 Η，s )， 3 · 8 6 ( 2 Η，t )， 4 · 3 5 ( 2 Η，t )， 5.68(2H，s)， t 7 ·〇 5 ( 2 H，m )， 7 · 1 2 ( 1 H，m )， 7 · 2 0 ( 1 H，m )， 7 .43 (lH?m)， 7 · 6 〇（1 H，m )， 8 · 3 4 ( 1 H，d )， 8 · 5 7 ( 1 H，d )， 11.03(lH，s)。 LRMS :m/z 407 (M+2)+o 本纸張尺度適用中國國家標準（CNS ) A4規格（21 OX 297公釐） -309 - (請先閱讀背面之注意事項再填寫本頁)524805 A7 B7 printed by the Consumer Cooperatives of the Central Bureau of Standards of the Ministry of Economic Affairs 5. Description of the invention (30 $ in agitation and containing the title compound of Preparation Example 1 3 2 (3 · 15 g, 7 · 4 5 mm ο 1) and n-propyl In an alcohol (40 m 1) solution, it was heated under reflux for 6 hours and then cooled. Then ethyl acetate (60 m 1) was added, and the resulting mixture was sequentially added with 1 M aqueous citric acid solution (2 5 m 1) and It was washed with brine (2 5 m 1), dried (M g S04) and evaporated under reduced pressure. The residue was subjected to column chromatography using dichloromethane: methanol (100: 0 to 9 5: 5) The title compound (2.17 g, 72%) was purified on a silica gel to elute the gradient. 5 (CDCl3): 1.29 (3H, t), 3.0 · 0 (2 Η, q), 3 · 5 7 (3 Η , S), 3 · 8 6 (2 Η, t), 4 · 3 5 (2 Η, t), 5.68 (2H, s), t 7 · 〇5 (2 H, m), 7 · 1 2 ( 1 H, m), 7 · 2 0 (1 H, m), 7. 43 (lH · m), 7 · 6 〇 (1 H, m), 8 · 3 4 (1 H, d), 8 · 5 7 (1 H, d), 11.03 (lH, s). LRMS: m / z 407 (M + 2) + o This paper size applies Chinese National Standard (CNS) A4 (21 OX 297) ) -309-- (Read the back of the precautions to fill out this page)

524805 經濟部中央標準局員工消費合作社印¾ A7 B7 五、發明説明（30》 製備例1 3 4 5 -氯磺醯基一 2 —正丙氧苄酸 在一個設有5 M aqueous氫氧化鈉scrub ( 5 5 0 m 1 )的三頸燒瓶裡添加硫醯氯（4 0 m 1 ，〇 · 5 5 m ο 1 )及氯磺酸（1 5 0 m 1 ，2 · 2 6 m ο 1 )，再把攪 拌的混合物冷卻至一 1 0 °C。在2 0分鐘時間內把2 -正 丙氧苄酸（l〇〇g ’ 0 · 55mo 1)於二氯甲烷（ 2 0 0 m 1 )中所形成的溶液加入，並確保反應混度維持 低於5 °C，接著令反應混合物升溫至室溫。在1小時內把 所得溶液加入一攪拌的冰水裡，同時維持溫度於大約0 t ，並持續攪拌3 0分鐘。混合物過濾後的固體用冷水（ 1〇〇m 1 )洗過，再真空乾燥而得呈白色固體之標題化 合物（122.2g，80%)。 5(DMS〇d6〇:1.13(3H，t)， 2 · 0 0 ( 2 Η，m )， 4 · 3 2 ( 2 Η，t )， 7 · 2 3 ( 1 Η，d )， 8.21 (lH，m)， 8 · 8 2 ( 1 H，d )。 製備例1 3 5 5 —（4 —乙基六氫吡啡一 1 一基磺醯基）一 2 —正 丙氧苄酸 在1 0分鐘內將1 —乙基六氫吡啡（1 3 5 m 1 ， 本紙張尺度適用中國國家標準（CNS ) A4規格（210X297公釐） -310 - (請先閱讀背面之注意事項再填寫本頁) 衣. 、11 524805 經濟部中央標準局員工消費合作社印製 A7 _____B7 ___ 五、發明説明（30冷 1 · 0 6 3 m ο 1 )加入經攪拌且以冰冷卻而含有製備例 134標題化合物（295 . 5g，1 · 06m〇1)與 水（1 · 2 <)的懸浮液裡，然後添加5 0 % w/ v氫氧 化鈉水溶液（6 4 m 1 ，〇 . 3 3 m ο 1 )，添加速度係 使P Η維持在6 - 7者。令反應混合物在低於1 〇 °C之溫 度攪拌2小時，把P Η調整至7，再於室溫下持續攪拌 1 8小時。接著以濃氫氯酸調整ρ Η至5，添加氯化鈉（ 2 4 〇 g )，再把所得混合物劇烈攪拌直到形成溶液。用 二氯甲烷（2 X 1 · 0 5 <)萃取該水溶液，萃取液合倂 後蒸除二氯甲烷，並以2 —丁酮代替二氯甲烷，以維持一 定體積，當head溫度達到大約7 7 °C時，把溶液冷卻到大 約3 6 °C ·接著在1小時內逐滴添加甲烷磺酸（5 9 m 1 ，0 · 909mo 1)及更多 2 — 丁酮（500ml)同 時逐漸加熱至7 5 °C以期能夠不斷攪拌。在室溫下將所得 懸浮液再攪拌1 8小時，過濾後的固體以2 —丁酮（ 5 0 0 m 1 )洗之，再於4 0 °C乾燥而得到標題化合物之 甲烷磺酸鹽（383g，80%)。 m.p.l87— 188〇C。 5(DMS〇d6):〇.97(3H，t)， 1 · 1 5 ( 3 Η，t )， 1 · 7 5 ( 2 Η，m )， 3 · 1 〇（4 Η，m )， 3 · 5 0 ( 2 Η，m )， 3.7〇（2H，m)， 本纸張尺度適用中國國家標準（CNS ) A4規格（210X 297公釐1 ^311 . ~ (請先閱讀背面之注意事項再填寫本頁)524805 Printed by the Consumer Cooperative of the Central Bureau of Standards of the Ministry of Economic Affairs ¾ A7 B7 V. Description of the Invention (30) Preparation Example 1 3 4 5 -Chlorosulfonyl-1 -n-propoxybenzyl acid in a 5 M aqueous sodium hydroxide scrub (500 m 1) in a three-necked flask was added thionine chloride (40 m 1, 0.5 5 m ο 1) and chlorosulfonic acid (150 m 1, 2 · 2 6 m ο 1), The stirred mixture was cooled to a temperature of 10 ° C. 2-n-propoxybenzoic acid (100 g '0 · 55mo 1) was dissolved in dichloromethane (2000 m 1) over a period of 20 minutes. The resulting solution was added and the reaction mixture was kept below 5 ° C, and then the reaction mixture was allowed to warm to room temperature. The resulting solution was added to a stirred ice water within 1 hour, while maintaining the temperature at about 0 t. Stirring was continued for 30 minutes. The solid after filtration of the mixture was washed with cold water (100 m 1) and dried in vacuo to give the title compound (122.2 g, 80%) as a white solid. 5 (DMS〇d60: 1.13 (3H, t), 2 · 0 0 (2 Η, m), 4 · 3 2 (2 Η, t), 7 · 2 3 (1 Η, d), 8.21 (lH, m), 8 · 8 2 (1 H, d). Preparation Example 1 3 5 5 (4-ethylhexahydropyridine-1, 1-sulfofluorenyl) -2-n-propoxybenzoic acid will be 1-ethylhexahydropyridine (1 3 5 m 1 in 10 minutes, this paper size applies China National Standard (CNS) A4 Specification (210X297 mm) -310-(Please read the precautions on the back before filling this page). 11 524805 Printed by the Consumers Cooperative of the Central Standards Bureau of the Ministry of Economic Affairs A7 _____B7 ___ V. Invention Explanation (30 cold 1 · 0 6 3 m ο 1) was added to a suspension containing ice 134 title compound (295. 5g, 1.06 m〇1) and water (1. 2 <) with stirring and cooling with ice. Then, a 50% w / v sodium hydroxide aqueous solution (6.4 4 m, 0.33 m ο 1) was added, and the rate of addition was such that P Η was maintained at 6-7. The reaction mixture was kept below 1 〇. Stir at 2 ° C for 2 hours, adjust P Η to 7, and continue to stir at room temperature for 18 hours. Then adjust ρ Η to 5 with concentrated hydrochloric acid, add sodium chloride (240 g), and then The resulting mixture was stirred vigorously until a solution was formed. The aqueous solution was extracted with dichloromethane (2 X 1 · 0 5 <), and the extract was combined and the dichloromethane was distilled off. And use 2-butanone instead of dichloromethane to maintain a certain volume. When the head temperature reaches about 7 7 ° C, cool the solution to about 36 ° C. Then add methanesulfonic acid dropwise over 1 hour ( 5 9 m 1, 0 · 909mo 1) and more 2-Butanone (500ml) is gradually heated to 7 5 ° C at the same time in order to continuously stir. The resulting suspension was stirred for an additional 18 hours at room temperature. The filtered solid was washed with 2-butanone (500 m 1) and dried at 40 ° C to give the methane sulfonate salt of the title compound ( 383g, 80%). m.p. 187-188 ° C. 5 (DMS〇d6): 0.97 (3H, t), 1 · 15 (3 Η, t), 1 · 7 5 (2 Η, m), 3 · 1 〇 (4 Η, m), 3 · 5 0 (2 Η, m), 3.7〇 (2H, m), this paper size is applicable to China National Standard (CNS) A4 specifications (210X 297 mm 1 ^ 311. ~ (Please read the precautions on the back before (Fill in this page)

經濟部中央標率局員工消費合作社印製 524805 A7 B7 五、發明説明（30$ 4 · 1 1 ( 2 Η，t )， 7 · 3 9 ( 1 Η，d )， 7 · 8 6 ( 1 Η，m )， 7 · 9 3 ( 1 Η，m )。 取一部份（2 0 g )該鹽溶在水（1 0 0 m 1 )中， 再用5 Μ氫氧化鈉水溶液調整p Η至5 . 3，然後添加氯 化鈉（2 6 g )。接著添加4 一甲基戊烷一 2 —酮（ 2 0 0 ml)，經劇烈攪拌3 0分鐘後過濾。得到的固體 經乾燥而得粗產物（1〇g，6 4 % ) ，m · p · 8 3 — 9 〇 °C，取其試樣以2 -丁酮：丙酮進行結晶而得到純標 題化合物。 m.p.143 — 145 t：。 5(DMS〇d6):〇.91(3H，t)， 0 · 9 9 ( 3 Η ; t )， 1 · 7 4 ( 2 Η，m )， 2 · 3 0 ( 2 Η，q )， 2 · 4 5 ( 4 Η，m )， 2 · 8 5 ( 4 Η，m )， 4.〇9(2H，t)， 7 · 3 2 ( 1 Η，d )， 了 · 7 〇（1 Η，d )， 7 · 8 7 ( 1 Η，s )。 L R M S ： m / z 357 (M+1)+。 本紙張尺度適用中國國家標準（CNS ) A4規格（210X 297公釐） -312 - (請先閲讀背面之注意事項再填寫本頁)Printed by the Employees Cooperative of the Central Standards Bureau of the Ministry of Economic Affairs 524805 A7 B7 V. Description of the invention (30 $ 4 · 1 1 (2 Η, t), 7 · 3 9 (1 Η, d), 7 · 8 6 (1 Η , M), 7 · 9 3 (1 Η, m). Take a part (20 g) of the salt and dissolve it in water (100 m 1), and adjust p Η to 5 mM sodium hydroxide aqueous solution. 5.3, then add sodium chloride (26 g). Then add 4-methylpentane-2-one (200 ml), stir vigorously for 30 minutes and filter. The obtained solid is dried to obtain The crude product (10 g, 64%), m · p · 8 3-90 ° C, a sample was taken and crystallized from 2-butanone: acetone to obtain the pure title compound. Mp143-145 t :. 5 (DMS〇d6): 0.91 (3H, t), 0.99 (3 Η; t), 1 · 7 4 (2 Η, m), 2 · 3 0 (2 Η, q), 2 · 4 5 (4 Η, m), 2 · 8 5 (4 Η, m), 4. 09 (2H, t), 7 · 3 2 (1 Η, d), · 7 〇 (1 Η, d), 7 · 8 7 (1 Η, s). LRMS: m / z 357 (M + 1) +. This paper size applies Chinese National Standard (CNS) A4 (210X 297 mm) -312-(Please Read first Note to fill out the back of this page)

524805 Α7 Β7 經濟部中央標準局員工消費合作社印製 五、發明説明（30 製備例1 3 6 3 —乙基一 4 —〔5 -（4 一乙基六氫吼哄一 1—基 磺醯基）—2 -正丙氧苄醯胺基〕—2—(吡啶—2 —基 )甲基吡唑一5 —甲醯胺 · 將製備例1 3 5標題化合物（3 5 6 · 5 g，1 ·〇 m ο 1 )與2 -丁酮（2 · 8 5 <)的經攪拌混合物加熱 迴流，然後在大氣壓下蒸餾直到去除相當量（1 · 〇 8 < )的溶劑。在氮氣下把所得溶液冷卻至室溫，再於2小時 內添加97%N，N —羰二咪唑（163 · 9g， 0 · 9 8m ο 1 )，使用 Archimedean screw 並用 2 — 丁酮 洗入（washing-in)。在1小時內將混合物加熱至迴流溫度 ，再攪拌3 0分鐘，冷卻，再於室溫下攪拌1 8小時。接 著利用2 —丁酮（2 0 m 1 )將製備例1 3 1之標題化合 物（2 4 5 · 3 έ，1 · 〇 m ο 1 )洗入.，將反應混合物 攪拌迴流3 2小時，然後在室溫下攪拌1 8小時。把所得 固體加以收集，以2 —丁酮（300ml ，然後15〇 m 1 )洗兩次，抽氣乾燥，然後與水（1 · 7 2 5 < )攪 拌3 0分鐘。過濾所得固體以水（2 1 5 m 1 )洗過，再 於5 5 °C乾燥而得灰色固體之標題化合物（3 8 5 · 1 g ，6 6 % )。 m · ρ · 1 9 1 — 1 9 2 °C。元素分析實測値：C， 57.43 ;Η，6·38 ·，Ν，16.69。 C28H37N7〇5S 計算値 c，57 · 62 ； Η，6·39;Ν，16·8〇。 本纸張尺度適用中國國家標準（CNS ) Α4規格（210X297公釐） -313 - (請先閱讀背面之注意事項再填寫本頁) 、1Τ 524805 經濟部中央標隼局員工消費合作社印製 A7 B7 五、發明説明（311> 5 ( C D C 1 3 ) :l.〇5(9H，m)， 2 ·〇 4 ( 2 Η，m )， 2 · 3 8 ( 2 Η，q )， 2 · 5 〇（4 Η，m )， 2 . 8 8 ( 2 Η，ci )， 3 ·〇 5 ( 4 Η，m )， 4 · 2 9 ( 2 Η，t )， 5 · 2 5 ( 1 Η，s )， 5 · 4 7 ( 2 Η，s )， 6 · 6 8 ( 1 Η，s )， 6 · 9 2 ( 1 Η，d )， 7 · 1 2 ( 1 Η，d )， 7 · 2 2 ( 1 Η，m )， 7 · 6 6 ( 1 Η，m )， 7 · 8 6 ( 1 Η，d )， 8 · 6 〇（2 Η ， m )， l〇.36(lH，s)° LRMS:m/z 584 (M+1)+。 生物活性 , 下表列出數個本發明化合物作爲c GMP PDE 5 抑制劑之體外活性。 (請先閱讀背面之注意事項再填寫本頁)524805 Α7 Β7 Printed by the Consumer Cooperatives of the Central Standards Bureau of the Ministry of Economic Affairs 5. Description of the invention (30 Preparation Example 1 3 6 3 —Ethyl 4 — [5-(4 Ethyl hexahydrozine) 1 —Sulfosulfonyl ) -2- (n-propoxybenzylamine)]-2- (pyridine-2-yl) methylpyrazole-5methylformamide · Preparation Example 1 3 5 The title compound (3 5 6 · 5 g, 1 〇m ο 1) and 2-butanone (2.85 <) stirred mixture is heated under reflux, and then distilled under atmospheric pressure until a considerable amount of solvent (1.08 <) is removed. The resulting solution was cooled to room temperature, and then 97% N, N-carbonyldiimidazole (163.9g, 0.98m ο 1) was added within 2 hours, using an Archimedean screw and washing-in with 2-butanone. The mixture was heated to reflux temperature within 1 hour, stirred for another 30 minutes, cooled, and stirred at room temperature for 18 hours. Then the title of Preparation Example 1 31 was made using 2-butanone (20 m 1). The compound (2 4 5 · 3, 1 · 0 m ο 1) was washed in. The reaction mixture was stirred under reflux for 3 2 hours, and then stirred at room temperature for 18 hours. The body was collected, washed twice with 2-butanone (300 ml, then 150 m 1), dried by suction, and then stirred with water (1.72 5 <) for 30 minutes. The resulting solid was filtered with water (2 1 5 m 1) Washed and dried at 5 5 ° C to give the title compound (3 8 5 · 1 g, 66%) as a gray solid. M · ρ · 1 9 1 — 1 9 2 ° C. Element Analytical measurement 値: C, 57.43; Η, 6.38 ·, Ν, 16.69. C28H37N7〇5S Calculate 値 c, 57 · 62; Η, 6.39; Ν, 16.80. This paper scale applies to China Standard (CNS) Α4 specification (210X297 mm) -313-(Please read the precautions on the back before filling this page), 1T 524805 Printed by the Consumer Cooperatives of the Central Bureau of Standards of the Ministry of Economic Affairs A7 B7 V. Description of the invention (311 > 5 (CDC 1 3): 1.05 (9H, m), 2.04 (2 μm, m), 2.38 (2 μm, q), 2.5.0 (4 μm, m), 2. 8 8 (2 Η, ci), 3 · 05 (4 Η, m), 4 · 2 9 (2 Η, t), 5 · 2 5 (1 Η, s), 5 · 4 7 (2 Η, s), 6 · 6 8 (1 Η, s), 6 · 9 2 (1 Η, d), 7 · 1 2 (1 Η, d), 7 · 2 2 (1 Η, m), 7 · 6 6 (1 Η, m), 7 · 8 6 (1 Η, d), 8 · 6 〇 (2 ，, m), 10.36 (lH, s) ° LRMS: m / z 584 (M + 1) +. Biological activity. The following table lists the in vitro activities of several compounds of the invention as c GMP PDE 5 inhibitors. (Please read the notes on the back before filling this page)

本纸張尺度適用中國國家標準（CNS ) A4規格（210X297公釐） -314 Ρίί件2a:第87 1 02657 號專利申請案中文說明書修正頁 民國89年11月呈 申請曰期 案 類 號 發明 新型This paper size is applicable to Chinese National Standard (CNS) A4 (210X297 mm) -314 Ρίί 2a: 87 1 02657 Patent Application Chinese Specification Revision Page Submitted in November 89, Republic of China, Application Date, Type, Invention, New

87 ^ 2E 24 B 87102657 (以上各攔由本局填註） 名稱 發明 創作> 修认補充 89.11. Λ 524805 籌|專利説明書 中文 英 文 姓 名 國 籍 住、居所 姓 名 (名稱） 具有抑制磷酸二酯_ (PDE — 5)作用之吡唑並[4, 3 — d] 嘧啶- 7 -酮類化合物及其製備方法、中間物與藥學組会物或獸_ 調配物87 ^ 2E 24 B 87102657 (the above are filled by the Bureau) Name Invention &Creation; Revision Supplement 89.11. Λ 524805 Preparation | Patent Specification Chinese English Name Nationality Residence, Residence Name (Name) Has Inhibited Phosphodiester_ ( PDE-5) pyrazolo [4, 3 — d] pyrimidin-7-one compound and preparation method, intermediate and pharmaceutical group meeting or animal _ compound

Pyrazolo 14,3-d) pyrimidine-7 one compounds having tlTe effec of inhibiting phosphodiesterase (PDE~5) and the preparati processes. or veterinary intermediates and pharmaceutical compositions ry formulations thereof (1)馬克♦邦納吉 Bunnage，Mark Edward 約翰♦馬莎 Mathias，John Paul (3) £_芬♦虫屈待 Street, Stephen Derek Albert (1) (1) 英國 （2)英國 英國肯特聖維琪籃斯蓋特路輝瑞研究中心 英國 )n 裝Pyrazolo 14,3-d) pyrimidine-7 one compounds having tlTe effec of inhibiting phosphodiesterase (PDE ~ 5) and the preparati processes. Or veterinary intermediates and pharmaceutical compositions ry formulations thereof (1) Mark Bonagie Bunnage, Mark Edward John ♦ Martha Mathias, John Paul (3) £ _Fen Trapped Street, Stephen Derek Albert (1) (1) United Kingdom (2) United Kingdom, Kent, St. Vicki Basket, Sgate Road, Pfizer Research Center, United Kingdom) n Pack

Pfizer Central Research, Ramsgate Road, Sandwich, Kent CT13 9NJ, United Kingdom 英國肯特聖維琪藍斯蓋特路輝瑞研究中心Pfizer Central Research, Ramsgate Road, Sandwich, Kent CT13 9NJ, United Kingdom

Pfizer Central Research, Ramsgate Road Sandwich CT13 9NJ, United Kingdom ， ’ 英國肯特聖維琪藍斯蓋特路輝瑞研究中心 (1)輝瑞股份有限公司 Pfizer Inc·Pfizer Central Research, Ramsgate Road Sandwich CT13 9NJ, United Kingdom, ’Pfizer Inc. (1) Pfizer Inc.

Kent 訂 t, 經濟部智总57凌：Ira (工消費合作社印製 國 籍 三、申請人 住、居所 (事務所） 代表人 姓 名 (1)美國 (1)美國紐約州•紐約♦東四二街二三五號 235 East 42nd Street， New Yopk， Νγ ioqiy u s a (1)艾倫•史匹戈爾 Spiegel, Allen J, 本纸張尺度適用中國國家標準（CNS ) A4規格（210X297公釐） 線 524805Kent Order, Ministry of Economics and Intellectual Property 57 Ling: Ira (Nationality printed by industrial and consumer cooperatives III. Applicant's residence and residence (office) Name of representative (1) United States (1) New York State • New York ♦ East 4th Street No.235, 235 East 42nd Street, New Yopk, Νγ ioqiy usa (1) Allen Spiegel, Allen J, This paper size applies to China National Standard (CNS) A4 specification (210X297 mm) line 524805

S9.U.I 申請曰期 87 年 2 月 24日 案 號 87102657 類 別 (以上各欄由本局填註） A4 C4 霉|專利説明書 中 文 發明 新型 名稱 英 文 姓 名 國 籍 安東尼♦伍德Wood, Anthony 發明 創作 人 住、居所 (4)英國(4)英國肯特聖維琪藍斯蓋特路輝瑞研究中心 Pfizer Central Research, Ramsgate Road, Sandwich, Ken CT13 9NJ, United Kingdom 裝 t, 訂 姓 名 (名稱） 線 經濟部智BN邊¾¾工4費合作社印製 申請人 國 籍 住、居所 (事務所） 代表人 姓 名 本紙張尺度適用中國國家標準（CNS ) A4規格（210X297公釐） 524805 Β9ΛΙΑ7 A7 B7 五、發明說明（1 ) 本發明是有關一系列可抑制環狀鳥苷3 5 / 一單 磷酸酯磷酸二酯酶（c G M p p d E s )之批11坐並〔4 ，3 - d〕嘧啶一 7 -酮類化合物。 吡唑並嘧啶衍 些美國專利中有相關揭示， U S 3 9 2 P D E抑制劑 5 3 8 5提出一系列作爲c — AMP 之6 —乙氧瀠基吼1:1坐並〔1 ，5 — a〕嚼[[定 衍生物。U S 3 9 3 9 1 6 1提出具有中央神經系統活 性之5 —烷基一 1 ’ 3 —二甲基—1 Η —吡唑並〔4，3 —d〕嘧啶—7 -酮衍生物。U S 4 0 9 3 6 1 7提出 一系列可用作c 一 A Μ P P D Ε抑制劑之3，5，7 - 三取代吡唑並〔1，5 - a〕嘧啶 U S 4 1 4 7 7 8 括四環衍生物與一種 P D E抑制劑，其提出幾種P D E抑制劑，包括1 Η - [I比 唑並〔3，4 一 b〕吡啶一 5 —甲酸乙酯之衍生物。 9提出Parkinson氏症之組合療法，包 P D E抑制劑，尤其是腦部作用 US 46 6 6 9 08提出作爲PDE第1型與第3型之 抑制劑的5 -苯基一吼哩並〔4，3 - d〕[P密u定一 7 酮 ^--------1--------- (請先閱讀背面之注意事項再填寫本頁) 經 濟 部 智 慧 財 產 局 員 工 消 費 合 作 社 印 製 衍生物，其中U S 5 2 4 該苯基係被多種官能基所取代 6 9 3 2及US 5290776提出2 呋喃基一三卩坐並〔1，5 - a〕〔 1 三啡及 唑並 抗腺苷的作用（例如 提出一系列經取代之 劑。 3 — a〕〔 1 ’ 3 ’ 5〕二啡衍生物，其會 血管擴張）°US 577695 苯衍生物’可用作P D E第IV型抑 拮 制 524805 A7 B7 五、發明說明（) 本發明之化1^物係第5型環狀鳥苷3 /，5 > -單磷 酸酯磷酸二酯酶（c G Μ P P D Ε 5 )之有效且選擇性 的抑制劑，因而在各種醫療領域具備實用性。 具體而言，此類化合物在治療雄性勃起官能障礙（ Μ E D )與雌性性官能障礙（F S D )有其價値，但顯然 將可用於治療其他強效性與選擇性c G Μ P P D Ε 5抑 制劑所適應之醫學病症，這類病症包括早產，痛經，良性 攝護腺肥大（Β Ρ Η )，膀胱出口阻塞，失禁，穩定性’ 不穩定性與各種（Prinzmetal)絞痛，高血壓，肺高血壓 充血性心臟衰竭，動脈硬化，減少血管開放的病症，如後 經皮transluminal冠狀血管造形術post-PTCA，末稍血管疾 病，中風，支氣管炎，過敏性氣喘，慢性氣喘，過敏性鼻 炎，青光眼，以及以腸能動性失調爲特徵之疾病（如刺激 性腸症候群I B S )。 因此本發明提出如式（I A )與式（I B )之化合物 -----------裝--------訂--------- (請先閱讀背面之注意事項再填寫本頁) 經濟部智慧財產局員工消費合作社印製S9.UI Application Date February 24, 87 Case No. 87102657 Category (the above columns are filled by this Office) A4 C4 Mold | Patent Specification Chinese Invention New Name English Name Nationality Anthony Wood, Anthony Inventor, Residence (4) United Kingdom (4) Pfizer Central Research, Ramsgate Road, Sandwich, Ken CT13 9NJ, United Kingdom Kent, St. Vicki Lansgate Road, Kent, United Kingdom ¾¾Work 4 fee cooperative prints the applicant's nationality residence, residence (office) Name of the representative This paper size applies the Chinese National Standard (CNS) A4 specification (210X297 mm) 524805 Β9ΛΙΑ7 A7 B7 V. Description of the invention (1) The present invention It is a series of 11 compounds which can inhibit cyclic guanosine 3 5 / monophosphate phosphodiesterase (c GM ppd E s) and [4,3-d] pyrimidine-7-one compounds. Pyrazolopyrimidine derivatives are disclosed in some US patents. US 3 9 2 PDE inhibitor 5 3 8 5 proposes a series of c-AMP-6-ethoxyfluorenyl groups 1: 1 sitting and [1, 5 — a 〕 Chew [[Ding derivative. U S 3 9 3 9 1 6 1 proposes a 5-alkyl- 1 1 '3-dimethyl-1 fluorene-pyrazolo [4,3-d] pyrimidin-7-one derivative having central nervous system activity. US 4 0 9 3 6 1 7 proposes a series of 3,5,7-trisubstituted pyrazolo [1,5 -a] pyrimidines useful as c-AM PPD E inhibitors. US 4 1 4 7 7 8 includes A tetracyclic derivative and a PDE inhibitor, which proposes several PDE inhibitors, including derivatives of 1 Η-[Izozo [3,4-b] pyridine-5-ethyl formate. 9 proposed a combination therapy of Parkinson's disease, including PDE inhibitors, especially brain effects US 46 6 6 9 08 proposed 5-phenyl-phenylalanine as an inhibitor of PDE type 1 and type 3 [4, 3-d] [Pamidin-7 ketone ^ -------- 1 --------- (Please read the precautions on the back before filling out this page) Staff of the Intellectual Property Bureau of the Ministry of Economic Affairs Derivatives printed by consumer cooperatives, in which US 5 2 4 the phenyl group is substituted with various functional groups 6 9 3 2 and US 5290776 propose 2 furanyl-trifluorene and [1,5-a] [1 Anti-Adenosine action (eg, a series of substituted agents is proposed. 3-a] [1 '3' 5] Dimorphine derivatives, which will vasodilate) ° US 577695 Benzene derivatives' can be used as PDE Type IV inhibitory 524805 A7 B7 V. Description of the invention () The 5th cyclic guanosine 3 /, 5 of the chemical system 1 of the present invention >-monophosphate phosphodiesterase (c G Μ PPD Ε 5 ) Is an effective and selective inhibitor, so it has practicality in various medical fields. Specifically, these compounds have their value in the treatment of male erectile dysfunction (MED) and female sexual dysfunction (FSD), but they will obviously be used to treat other potent and selective c G M PPD E 5 inhibitors Adapted medical conditions, such as premature birth, dysmenorrhea, benign prostatic hypertrophy (ΒΡΗ), bladder outlet obstruction, incontinence, stability 'Prinzmetal colic, hypertension, high lung Blood pressure congestive heart failure, arteriosclerosis, reduced vascular openness, such as post-percutaneous transluminal coronary angioplasty post-PTCA, terminal vascular disease, stroke, bronchitis, allergic asthma, chronic asthma, allergic rhinitis, glaucoma , And diseases characterized by intestinal motility disorders (such as irritable bowel syndrome IBS). Therefore, the present invention proposes compounds such as formula (IA) and formula (IB) ----------- install -------- order --------- (please read first Note on the back, please fill in this page) Printed by the Consumer Cooperatives of the Intellectual Property Bureau of the Ministry of Economic Affairs

本紙張尺度適用中國國家標準_織格，禮）_ 524805 A7 B7___ 五、發明說明（） 18 (請先閱讀背面之注意事項再填寫本頁) 過量之試劑（如N，N > -羰二咪唑）於適當溶劑（如乙 酸乙酯或2 -丁酮）裡在約室溫至約8 0 °C之溫度下加以 活化，然後令中間物imidazolide與式（X A )或（X B ) 化合物在約2 0至約9 0 °C之溫度下反應。 式（瓜）胺，式（VEI) ， （XA)及（XB)之 4 — 胺基吡唑—5 -甲醯胺，式（丽）羧酸衍生物及式（X I )羧酸若無法購得或在後文中未加以說明，則可用製備例 中所述類似方法或依有機化學標準教科書或先前的文獻藉 慣用的合成步驟由易於取得的起始物質利用適當的試劑與 反應條件製得。 此外，熟習此項技藝者將可知道下文中實施例與製備 例（以得到式（I A )與（I B )化合物）所述方法的各 種變體與替代方法。 經濟部智慧財產局員工消費合作社印製 含有鹼性中心之式（I A )與（I B )化合物的藥學 上可接受鹽類也可用慣用方法製得。例如將該自由鹼的溶 液以適當的酸在不使用溶劑下或於適當溶劑中加以處理， 所得的鹽類以過濾方式或以真空蒸除溶劑之方式分離出來 ，藥學上可接受之鹼加成鹽可依類似方式令式（I A )或 (I B )化合物之溶液以適當鹼處理。這兩種類型的鹽類 可利用離子交換樹脂技術形成或互相轉化。 本發明化合物之生物活性係依以下測試方法測得。 磷酸二酯酶（P D E )抑制活性 對環狀鳥苷，5< -單磷酸酯（cGMP)磷酸 ^紙張尺度適用中國國家標準（CNS)A4規格（210 X 297公釐） -21 - 524805 ' A7 ____ B7 五、發明說明（19 ) 二酯酶與環狀腺苷3 / ，5 / -單磷酸酯（c A Μ P )磷 酸二酯酶之體外P D Ε抑制活性係以測量其I c 5 〇値（ 5〇％抑制酶活性所需化合物之濃度）而測得。 所需要的P D Ε酶係依W.J. Thompson與Μ.Μ. Appleman (Biochem·，1971，1^_，311)之方法由各種來源取得 ’包括人類海綿體（corpus cavernosum)，人類與兔子的 血小板，人類心室，人類骨骼肌及牛視網膜。特言之， c G Μ P -特異性P D E ( P D E 5 )及經c G Μ P抑制 之c A Μ P P D E ( P D Ε 3 )是取自人類海綿體組織， 人類血小板或兔子血小板；經c G Μ Ρ刺激之P D Ε ( P D Ε 2 )係取自人類海綿體；依賴鈣/攜鈣素（. calmodulin ) (Ca/CAM)之 PDE(PDEl)取自 人類心室；c A Μ P -特異性P D E ( P D E 4 )得自人 類骨骼肌；光受體PDE(PDE6)得自牛的視網膜。 以 W.J. Thompson 等人（Biochem·，1 979，1_8_,5 22 8 )之 「批次」法經過修飾而進行分析，測試結果顯示本發明化 合物爲c G Μ P -特異性P D E 5之有效且選擇性的抑制 劑。 功能活性 以 S.A· Ballard 等人（Brit. J. Pharmacol.，1996，118( suppl·)，abstract 153P)所述方式測定本發明化合物提高硝 普鈉（sodium nitroprusside)所誘發鬆驰預先收縮之兔子 海綿體組織細條的能力以進行體外評估。 本紙張尺度適用中國國家標準（CNS)A4規格（210 X 297公釐） (請先閱讀背面之注意事項再填寫本頁)This paper size applies the Chinese national standard _ Grid, etiquette _ 524805 A7 B7___ V. Description of the invention () 18 (Please read the precautions on the back before filling this page) Excessive reagents (such as N, N > -Carbodi Imidazole) in an appropriate solvent (such as ethyl acetate or 2-butanone) at a temperature of about room temperature to about 80 ° C, and then the intermediate imidazolide and the compound of the formula (XA) or (XB) in about Reaction at a temperature of 20 to about 90 ° C. If the formula (citrulline) amine, formula (VEI), (XA) and (XB) 4-aminopyrazole-5-formamidine, carboxylic acid derivatives of formula (Mexico) and carboxylic acids of formula (XI) are not available for purchase If it is obtained or not described in the following, it can be prepared by a similar method as described in the preparation examples or by using conventional synthetic procedures according to organic chemical standard textbooks or previous literature, using readily available starting materials, using appropriate reagents and reaction conditions. In addition, those skilled in the art will know various variations and alternatives of the methods described in the examples and preparations below to obtain compounds of formulae (IA) and (IB). Printed by the Consumer Cooperative of the Intellectual Property Bureau of the Ministry of Economic Affairs. Pharmaceutically acceptable salts containing compounds of the formulae (I A) and (I B) with basic centers can also be prepared by conventional methods. For example, the solution of the free base is treated with a suitable acid without using a solvent or in a suitable solvent, and the obtained salts are separated by filtration or vacuum distillation to remove the solvent. A pharmaceutically acceptable base addition The salt can be treated in a similar manner with a solution of a compound of formula (IA) or (IB) with a suitable base. These two types of salts can be formed or converted into each other using ion exchange resin technology. The biological activity of the compounds of the present invention was measured according to the following test methods. Phosphodiesterase (PDE) inhibitory activity on cyclic guanosine, 5 < -monophosphate (cGMP) phosphate ^ Paper size applies Chinese National Standard (CNS) A4 specification (210 X 297 mm) -21-524805 'A7 ____ B7 V. Description of the invention (19) The in vitro PD Ε inhibitory activity of diesterase and cyclic adenosine 3 /, 5 /-monophosphate (c A MP) phosphodiesterase is to measure its I c 5 〇値 (concentration of a compound required to inhibit enzyme activity by 50%). The required PD E enzymes were obtained from various sources according to the methods of WJ Thompson and M.M. Appleman (Biochem., 1971, 1__, 311), including human corpus cavernosum, human and rabbit platelets, Human ventricle, human skeletal muscle and bovine retina. In particular, c G MP-specific PDE (PDE 5) and c A Μ PPDE (PD Ε 3) inhibited by c G MP are taken from human cavernous tissue, human platelets or rabbit platelets; via c G MPE-stimulated PD Ε (PD Ε 2) was taken from human corpus cavernosum; calcium-dependent / calcium-containing (. Calmodulin) (Ca / CAM) -derived PDE (PDEl) was taken from human ventricles; c A MP P-specificity PDE (PDE 4) was obtained from human skeletal muscle; the photoreceptor PDE (PDE6) was obtained from bovine retina. WJ Thompson et al. (Biochem., 1 979, 1_8_, 5 22 8) was modified and analyzed by the "batch" method. The test results show that the compound of the present invention is effective and selectable as c G M P -specific PDE 5. Sexual inhibitors. Functional activity was measured in the manner described by SA Ballard et al. (Brit. J. Pharmacol., 1996, 118 (suppl.), Abstract 153P). The compounds of the present invention increased relaxation induced by sodium nitroprusside induced relaxation in rabbits The ability of the corpus cavernosa tissue to be evaluated in vitro. This paper size applies to China National Standard (CNS) A4 (210 X 297 mm) (Please read the precautions on the back before filling this page)

· n n n —.1 n I— HI 一口 T m- I I la ·ϋ n n I I 經濟部智慧財產局員工消費合作杜印製 524805 經濟部智慧財產局員工消費合作社印製 A7 B7 五、發明說明（21 ) 患決定最適當的實際服用量，而且會依病患的年齡，體重 及反應加以改變。上述服用量是就一般情況而言，可因個 別情況而有較大或較小的服用量範圍，此乃屬本發明範圍 內。 大體上本發明化合物在用於人類時，係以口服方式爲 較佳之途徑，因其最爲方便，而且例如在me D內可避免 已知因海綿體內（i · c ·)投與所聯帶產生的缺點。對 一個典型的男人而言在MED之較佳口服服藥條件（oral dosing regimen )在需要時爲2 5至1 0 Omg。如果服藥 者有吞11燕的問題或者在口服後有藥物吸收減少（i m p a i r m e n t )的問題，則可用非經腸方式給藥，例如透過舌下或頰內 含藥方式投與。 在獸醫用途時，式（I A )或（I B )化合物或其獸 醫學上可接受之鹽類或其獸醫學上可接受之溶劑合物係依 一般獸醫實務以適當的可接受調配物施予。獸醫師會定出 最適合特定動物的服藥條件與施藥途徑。 故本發明提供一種含有式（I A )或（I B )化合物 或其藥學上可接受鹽類或其藥學上可接受溶劑合物，且連 同藥學上可接受稀釋劑或載體之藥學組合物。 本發明還提供一種含有式（I A )或（I B )化合物 ，或其獸醫學上可接受鹽類，或其獸醫學上可接受溶劑合 物，且連同獸醫學上可接受稀釋劑或載體之獸醫調配物。 本發明亦提供一種如式（1 A )或（I B )之化合物 ，或其藥學上可接受之鹽類，或其藥學上可接受之溶劑合 本紙張尺度適用中國國家標準（CNS)A4規格（210 X 297公釐） 一 24 一 ------------裝--------訂--------- (請先閱讀背面之注意事項再填寫本頁) 524805 經濟部智慧財產局員工消費合作社印製 A7 B7 五、發明說明（22 ) 物，或含有前述任一物質之藥學組合物，以用作人類之醫 藥品。 此外，本發明提供一種如式（I A )或（I B )之化 合物，或其獸醫學上可接受之鹽類，或其獸醫學上可接受 之溶劑合物，或含有前述任一物質之獸醫調配物，以用作 動物之醫藥品。 本發明再一方面提出一種如式（I A)或（I B)之 化合物，或其藥學上可接受之鹽類，或其藥學上可接受之 溶劑合物在製造一種用於治療或預防c G Μ P P D Ε 5 抑制劑所適應醫學病症的人類醫藥品之用途。 本發明也提出一種如式（I A )或（I Β )之化合物 ，或其獸醫學上可接受之鹽類，或其獸醫學上可接受之溶 劑合物在製造一種用於治療或預防c G Μ P P D Ε 5抑 制劑所適應之醫學病症的動物醫藥品之用途。 又，本發明提出一種如式（I Α)或（I Β)之化合 物，或其藥學上可接受之鹽類，或其藥學上可接受之溶劑 合物在製造一種用於治療或預防下列醫學病症之人類醫藥 品的用途：雄性勃起官能障礙，雌性性官能障礙，早產， 痛經，良性攝護腺肥大（Β Ρ Η )，膀胱出口阻塞，失禁 ，穩定性，不穩定性與各種（Pnnzmetal )絞痛，高血壓， 肺高血壓，充血性心臟衰竭，動脈硬化，中風，末稍血管 疾病，減少血管開放的病症，慢性氣喘，支氣管炎，過敏 性氣喘，過敏性鼻炎，青光眼，以及以腸能動性失調爲特 徵之疾病。 本紙張尺度適用中國國家標準（CNS)A4規格（210 X 297公釐） 一 25 -· Nnn —.1 n I— HI Tm- II la · ϋ nn II Printed by the Consumers ’Cooperative of Intellectual Property Bureau of the Ministry of Economic Affairs 524805 Printed by the Consumers’ Cooperative of the Intellectual Property Bureau of the Ministry of Economic Affairs A7 B7 V. Invention Description (21) The patient decides the most appropriate actual dosage, and it will change according to the patient's age, weight and response. The above-mentioned dosage is generally within a range of a larger or smaller dosage due to individual circumstances, which is within the scope of the present invention. In general, the compounds of the present invention are preferably administered orally when used in humans, because they are the most convenient, and for example, in me D, it is possible to avoid the known intracorporeal (i.c.). The resulting disadvantages. For a typical man, the preferred oral dosing regimen in the MED is 25 to 100 mg when needed. If the user has the problem of swallowing 11 swallows or the problem of reduced drug absorption (i m p a i r m e n t) after oral administration, it can be administered parenterally, for example by sublingual or buccal administration. For veterinary use, the compounds of formula (IA) or (IB) or their veterinary acceptable salts or their veterinary acceptable solvates are administered in accordance with general veterinary practice with appropriate acceptable formulations. Veterinarians will determine the conditions and routes of administration that are most suitable for a particular animal. Therefore, the present invention provides a pharmaceutical composition containing a compound of the formula (I A) or (I B) or a pharmaceutically acceptable salt thereof or a pharmaceutically acceptable solvate thereof, together with a pharmaceutically acceptable diluent or carrier. The invention also provides a veterinary medicine comprising a compound of formula (IA) or (IB), or a veterinarily acceptable salt thereof, or a veterinarily acceptable solvate thereof, together with a veterinarily acceptable diluent or carrier. Preparations. The present invention also provides a compound such as formula (1 A) or (IB), or a pharmaceutically acceptable salt thereof, or a pharmaceutically acceptable solvent thereof. The paper size is applicable to the Chinese National Standard (CNS) A4 specification ( 210 X 297 mm) one 24 one ------------ install -------- order --------- (please read the precautions on the back before filling This page) 524805 A7 B7 printed by the Consumer Cooperatives of the Intellectual Property Bureau of the Ministry of Economic Affairs. 5. Description of Invention (22), or a pharmaceutical composition containing any of the foregoing, for use as a pharmaceutical for humans. In addition, the present invention provides a compound of formula (IA) or (IB), or a veterinarily acceptable salt thereof, or a veterinarily acceptable solvate thereof, or a veterinary formulation containing any of the foregoing. To be used as medicine for animals. In another aspect of the present invention, a compound of formula (IA) or (IB), or a pharmaceutically acceptable salt thereof, or a pharmaceutically acceptable solvate thereof is provided for the manufacture of a compound for treating or preventing c G M Use of PPD E 5 inhibitors as human pharmaceuticals for medical conditions. The present invention also proposes a compound of formula (IA) or (IB), or a veterinarily acceptable salt thereof, or a veterinarily acceptable solvate thereof in the manufacture of a compound for treating or preventing cG Use of animal medicines for medical conditions to which MPPD E 5 inhibitors are adapted. In addition, the present invention proposes a compound of formula (I A) or (I B), or a pharmaceutically acceptable salt thereof, or a pharmaceutically acceptable solvate thereof in the manufacture of a medicine for treating or preventing the following medicines The use of human medicines for diseases: male erectile dysfunction, female dysfunction, premature birth, dysmenorrhea, benign prostatic hypertrophy (ΒΡ), bladder outlet obstruction, incontinence, stability, instability and various Colic, High Blood Pressure, Pulmonary Hypertension, Congestive Heart Failure, Arteriosclerosis, Stroke, Terminal Vascular Disease, Reduced Vascular Disorders, Chronic Asthma, Bronchitis, Allergic Asthma, Allergic Rhinitis, Glaucoma, and Bowel Diseases characterized by motility disorders. This paper size applies to China National Standard (CNS) A4 (210 X 297 mm)-25-

Aw --------tr--------- (請先閱讀背面之注意事項再填寫本頁) 524805 mMA7 A7 B7 經濟部智慧財產局員工消費合作社印製 五、發明說明（^3 ) 本發明也提出一種如式（I A )或（I B )之化合物 ’或其獸醫學上可接受之鹽類，或其獸醫學上可接受之溶 劑合物在製造一種用於治療或預防下列醫學病症之人類醫 藥品的用途：雄性勃起官能障礙，雌性性官能障礙，早產 ，痛經，良性攝護腺肥大（B P Η )，膀胱出口阻塞，失 禁，穩定性，不穩定性與各種（Prinzmetal )絞痛，高血壓 ，肺高血壓，充血性心臟衰竭，動脈硬化，中風，末稍血 管疾病，減少血管開放的病症，慢性氣喘，支氣管炎，過 敏性氣喘，過敏性鼻炎，青光眼，以及以腸能動性失調爲 特徵之疾病。 再者，本發明提出一種治療或預防哺乳動物（包括人 類）c G Μ P P D Ε 5抑制劑所適應醫學病症的方法， 包括對該哺乳動物施以有效治療量的式（I A )或（I Β )之化合物，或其藥學上或獸醫學上可接受之鹽類，或其 藥學上或獸醫學上可接受之溶劑合物，或含有前述任一物 質之藥學組合物或獸醫調配物。 本發明更進一步提出一種治療或預防哺乳動物（包括 人類）以下病症之方法：雄性勃起官能障礙，雌性性官能 障礙，早產，痛經，良性攝護腺肥大（Β P Η )，膀胱出 口阻塞，失禁，穩定性，不穩定性與各種（Pnnzmeul )絞 痛，高血壓，肺高血壓，充血性心臟衰竭，動脈硬化，中 風，末稍血管疾病，減少血管開放的病症，慢性氣喘，支 氣管炎，過敏性氣喘，過敏性鼻炎，青光眼，以及以腸能 動性失調爲特徵之疾病，此方法包括對該哺乳動物施以有 (請先閱讀背面之注意事項再填寫本頁) 裝 ϋ i^i ·ϋ n I ，a I i ϋ I n n I * =口 本紙張尺度適用中國國家標準（CNS)A4規格（210 X 297公釐） -26 - 524805 89.IL 17 A7 B7 五、發明說明右2 ) 實施例編號 I C 5 〇 ( η Μ ) 4 2 · 2 7 2 . 6 3 1 4.0 7 7 7 . 1 4 1 3 . 9 8 7 12.0 1〇〇 1 . 9 1〇8 2 . 1 117 3 . 2 1 2 5 2 . 8 12 6 9 . 2 12 9 6 . 5 (請先閱讀背面之注意事項再填寫本頁) 經濟部智慧財產局員工消費合作社印製 安全性 有數個本發明化合物已以高達3 m g / k g對老鼠靜 脈注射（1 . v · ) ，0 . 5 m g / k g對狗靜脈注射以 及1 m g / k g令狗口服"（p · ο ·)等劑量進行測試， 結果並未發現有不利的效應。 t 0 0 (CNS)A4 (21〇，297 3i5 一Aw -------- tr --------- (Please read the notes on the back before filling this page) 524805 mMA7 A7 B7 Printed by the Consumer Cooperatives of the Intellectual Property Bureau of the Ministry of Economic Affairs (^ 3) The present invention also proposes a compound such as formula (IA) or (IB) 'or a veterinary acceptable salt thereof, or a veterinary acceptable solvate thereof in the manufacture of a Use of human medicine to prevent the following medical conditions: male erectile dysfunction, female dysfunction, premature birth, dysmenorrhea, benign prostatic hypertrophy (BP Η), bladder outlet obstruction, incontinence, stability, instability and various ( Prinzmetal) colic, hypertension, pulmonary hypertension, congestive heart failure, arteriosclerosis, stroke, terminal vascular disease, conditions that reduce vascular openness, chronic asthma, bronchitis, allergic asthma, allergic rhinitis, glaucoma, and Diseases characterized by intestinal motility disorders. Furthermore, the present invention provides a method for treating or preventing a medical condition to which c G M PPD E 5 inhibitor is adapted in mammals (including humans), which comprises administering to the mammal an effective therapeutic amount of formula (IA) or (IB) ), Or a pharmaceutically or veterinarily acceptable salt thereof, or a pharmaceutically or veterinarily acceptable solvate thereof, or a pharmaceutical composition or veterinary formulation containing any of the foregoing. The invention further proposes a method for treating or preventing the following diseases in mammals (including humans): male erectile dysfunction, female dysfunction, premature birth, dysmenorrhea, benign prostate hypertrophy (B P Η), bladder outlet obstruction, incontinence , Stability, instability and various (Pnnzmeul) colic, hypertension, pulmonary hypertension, congestive heart failure, arteriosclerosis, stroke, terminal vascular disease, reduced vascular openness, chronic asthma, bronchitis, allergies Asthma, allergic rhinitis, glaucoma, and diseases characterized by intestinal motility disorders, this method includes applying the mammal (please read the precautions on the back before filling out this page) Decoration i ^ i · ϋ n I, a I i ϋ I nn I * = The size of the paper is applicable to the Chinese National Standard (CNS) A4 (210 X 297 mm) -26-524805 89.IL 17 A7 B7 V. Description of the right 2) Examples Number IC 5 0 (η Μ) 4 2 · 2 7 2. 6 3 1 4.0 7 7 7. 1 4 1 3. 9 8 7 12.0 1 0 0 1. 9 1 0 8 2. 1 117 3. 2 1 2 5 2. 8 12 6 9. 2 12 9 6. 5 (please first Read the notes on the back and fill in this page again.) Safety printed by the Consumer Cooperatives of the Intellectual Property Bureau of the Ministry of Economic Affairs. Several compounds of the present invention have been injected intravenously in rats at up to 3 mg / kg (1.v ·), 0.5 mg / kg was tested intravenously in dogs and 1 mg / kg orally administered dogs (p · ο ·) and other doses were tested. No adverse effects were found. t 0 0 (CNS) A4 (21〇, 297 3i5 1

Claims (1)

A8 B8 C8 D8 524805 , fL· 六、申請專利範圍 附件一 a : 第87102657號專利申請案 中文申請專利範圍修正本 民國91年11月26日修正 ；L .一種如式（I A )或（I B )之化合物A8 B8 C8 D8 524805, fL. VI. Annex I to the scope of patent application: Patent Application No. 87102657 Amendment of Chinese Patent Application Amendment November 26, 1991 Amended by the Republic of China; L. A formula (IA) or (IB) Compound (請先閲讀背面之注意事項再填寫本頁) (IA) (IB) 或其藥學上或獸醫學上可接受之鹽類， 其中R1爲Ci— C3烷基，（CH2)nHet或 (C H 2 ) n A r，其中該C i — C 3烷基係經C 3 — C 6環 烷基，C〇N R 5 R 6或以N -連結之雜環基所取代，此雜 環基係選自吡唑基，三唑基，嗎啉基及4 - R 9 -六氫吡哄 基； 經濟部智慧財產局員工消費合作社印製 R 2爲C i — C 6烷基 R 3爲選擇性經c i 一 C ‘ 4烷氧基所取代之C 1 — C 1 5院 基； R 4 爲 S 〇 2 N R 7 R 8 · J R 5爲Η ; R 6係選擇性經C i — C 4烷氧基所取代之C i 一 C 4焼 基， 或者R 5與R 6連同與其連接之氮原子形成嗎啉基； 本紙張尺度適用中國國家標準（CNS ) A4規格（210X297公釐了 524805 A8 B8 C8 D8 六、申請專利範圍 R7與R8連同與其相接之氮原子形成4 一 R1C) -六氫 吡畊基； R9爲Ci — 〇4焼基； R 1 ◦爲Η或選擇性經〇Η，C ! — C 4烷氧基或 C〇N Η 2所取代之C ! — C 4烷基； H e t係選自吡啶基，1 —氧吡啶基（Ιο X i d 〇 p y r i d i n y 1 ) ， 嗜1 卩井基 ，嘧 卩定基 ，卩比哄基 ，味 卩坐基 ，異 哼唑基，噻唑基，三唑基，及噚二唑基，而任一者均可選 擇性經一或二個選自C 1 一 C 4院基（選擇性經C 1 一 C· 4院 氧基所取代），Ci — C4烷氧基及NH22取代基所取代 J A r爲選擇性經一或二個選自C χ — C 4烷基，C i — C4烷氧基，鹵基，CN， C〇NH2， N〇2， NH2, NHS〇2 (Ci-C、烷基）及S〇2NH2之取代基所取 代之苯基；且 η爲◦或1。 2 .如申請專利範圍第1項之化合物，其中R 1係經 C3 — C5環烷基，C〇NR5R6或Ν —連結之雜環基（選 自吡唑基，三唑基，嗎啉基及4 一 R 9 -六氫吡啡基）所取 代之Cl— C2院基；（CH2) nHe t或 (C H 2 ) n A r ; R 5爲Η而R 6爲選擇性經C ! — C 4烷 氧基所取代之C C4烷基或者R5與R6連同與其連接之 氮原子形成嗎啉基；H e t係選自吡啶基，1 一氧吡啶基 (Ι-oxidopyddinyl)，嗒畊基，嘧啶基，吡哄基，咪唑基 本紙張尺度適用中國國家襟準（CNS ) M規格（210X297公釐） -2 - (請先閱讀背面之注意事項再填寫本頁) •裝· 訂 -LP 經濟部智慧財產局員工消費合作社印製 524805 A8 B8 C8 --------__ 六、申請祠關 ~~" -- ，異噚唑基，噻唑基，三唑基，及腭二唑基，而任一者均 可選擇性經一或二個選自CH3，CH2CH2〇CH3， 〇CH3及NH2之取代基所取代；且r2，r3 r 4 (請先閲讀背面之注意事項再填寫本頁) R 9，A r和n均如申請專利範圍第丄項所定義者。 3 _如申請專利範圍第2項之化合物，其中R :係經環 丁基，C〇NR5R6，吡唑一 1—基，1，2， 3 —三哩 —1—基，1，2，4 —三唑—1—基，嗎啉一 4 一基， 或4 —甲基六氫吡畊一 1 一基所取代之◦ 1 一 c 2烷基；嘧 D定一 2 —基；CH2He t 或（CH2) ηΑι· ; R2 爲 一 C 3烷基；R 3爲選擇性經C i — C 2烷氧基所取代之C i —C 3烷基；R 5爲Η而R 6爲選擇性經c 1 一 C 2烷氧基所 取代之C C2烷基或者R5與R6連同與其連接之氮原子 形成嗎啉一 4 一基；R 1。爲選擇性經〇η，〇C Η 3或 C〇Ν Η 2單取代之C i 一 C 2烷基；H e t係選自吡啶一 經濟部智慧財產局員工消費合作社印製 2 —基，1 —氧吡啶一 2 -基，吡啶一 3 —基，嗒畊—3 一基，嗒哄—4 一基，嘧啶—4 —基，嘧啶—5 —基，口比 啡—2 —基，3 -甲氧d比n定—2 —基，6 —胺基13比卩定—2 —基，1 一甲基咪唑一 2 -基，3，5 -二甲基異噚唑— 4 —基，2 —甲基噻唑—4 —基，1 一甲基一1，2，4 -三唑一5 —基，1— (2 —甲氧乙基）—1，2，4 — 三唑一 5 —基，4 一甲基—1，2，4 一三唑—3 —基， 3 —甲基—1，2，4 —三唑—5 —基，1，2，4 —腭 二唑一 3 —基及5 —甲基—1，2，4 一鳄二唑一3 —基 ;Αχ*係選自苯基，4 一氯苯基，4 一溴苯基，2 -氰苯 本紙張尺度適用中國國家標準（CNS ) Α4規格（210 X 297公釐） -3 - 經濟部智慧財產局員工消費合作社印製 524805 A8 B8 C8 _ D8 六、申請專利範圍 基，2-胺羰基苯基，4一胺羰基苯基，2-硝苯基，4 一硝苯基.，2 —胺苯基，4 一胺苯基，2 -甲烷磺醯胺苯 基，4 _甲烷磺醯胺苯基，4 一乙烷磺醯胺苯基，4 一（ 丙〜2-基磺醯胺基）苯基，及4一胺磺醯基苯基；且η 係如申請專利範圍第2項所定義者。 4 ·如申請專利範圍第3項之化合物，其中R 1係環丁 基甲基，嗎琳一 4 一基鑛甲基，2 —(嗎琳一 4 一基）乙 基，嘧啶—2 —基，CH2He t 或（CH2) nAr ; R2 係 CH2CH3 或 CH2CH2CH3 ; R3 爲 CH2CH3， CH2CH2CH3 或 CH2CH2〇CH3 ; R10 爲 ch3, CH2CH3或CH2CH2〇H ; He t係選自吡啶一2 — 基，嗒畊—3 -基，吡畊一 2 -基，3 —甲氧吡啶一 2 — 基，6 —胺吡啶—2 -基，1—甲基咪唑一 2 —基，3， 5 —二甲基異噚唑一4 —基，1—甲基一1，2，4 —三 唑〜5 —基，1— (2 —甲氧乙基）—1，2，4 —三唑 —5 —基及5 —甲基—1，2，4 —噚二唑_3—基；A r爲選自苯基，2 -胺苯基，2 —甲烷磺醯胺苯基，4 一 甲烷磺醯胺苯基，4 一乙烷磺醯胺苯基及4 一（丙一 2 -基磺醯胺基）苯基；且η係如申請專利範圍第3項中所定 義者。 5 .如申請專利範圍第4項之化合物，其中該式（ I A )或（I Β )之化合物係選自 5 — {5 —〔4 一（2 —翔乙基）六氣吼哄一 1一基 磺醯基〕一 2 -正丙氧苯基丨一 3 -正丙基一 1 一（吡啶 ---------------訂------9 (請先閱讀背面之注意事項再填寫本頁) 本紙張尺度適用中國國家標準（CNS ) A4規格（210X297公釐） -4 - 524805 A8 B8 C8 D8 穴、申請專利範圍 一 2 —基）甲基—1，6 —二氫—7Η -吡唑並〔4，3 一 d〕卩密卩定—7 —酮； (請先閲讀背面之注意事項再填寫本頁) 1— (1 一甲基咪唑一 2 —基）甲基一5 —〔5 —( 4 一甲基六氫吡啡一 1-基磺醯基）一 2 -正丙氧苯基〕 一 3 —正丙基—1，6 -二氫—7H —吡唑並〔4，3 -d〕卩密卩定一 7 —酮； 5 — {5 —〔4 — (2 -羥乙基）六氫吡啡一 1 一基 磺醯基〕一 2 -正丙氧苯基丨—3 -正丙基一 2 -（吡啶 一 2 —基）甲基—2，6 —二氫—7H —吡唑並〔4，·3 —d〕嘧卩定—7 —酮； 5 -〔 5 — ( 4 -乙基六氫吡畊—1 一基磺醯基）— 2 —正两氧苯基〕—3 —正丙基一 2 — (D比卩定—2 —基） 甲基一 2，6 —二氫—7 Η —吡唑並〔4，3 — d〕嘧啶 —7 -酮； 經濟部智慧財產局員工消費合作社印製 3 —乙基一 5 —〔5 — (4 —乙基六氫吡啡一 1—基 磺醯基）—2 -正丙氧苯基〕一 2 -（吡啶—2 -基）甲 基—2，6 -二氫—7 Η -吡唑並〔4，3 - d〕嘧啶一 7 —酮； 5 —〔 5 -（ 4 —乙基六氫吡畊一 1 一基磺醯基）一 2 -正丙氧苯基〕—3 -正丙基一 2 -（嗒畊一 3 -基） 甲基—2，6 —二氫—7 Η —吡唑並〔4，3 - d〕嘧啶 -7.—酮； 5 -〔5 -（4 一乙基六氫吡畊—1 一基磺醯基）— 2 -正丙氧苯基〕—3 -正丙基一 2—(塔哄—2 -基） 本紙張尺度適用中國國家標準（CNS ) A4規格（210X297公釐） -5 - 524805 A8 B8 C8 D8 六、申請專利範圍 甲基一 2，6 —二氫一 7H —吡唑並〔4， 3 - d〕嘧啶 一 7 —酮；以及 (請先閱讀背面之注意事項再填寫本頁) 5 —〔2—乙氧基—5— (4—乙基六氫d比畊—1一 基磺醯基）苯基〕一 3 —正丙基—2 —(吡啶一 2 —基） 甲基一2，6 —二氨一 7H—D比卩坐並〔4，3 — d〕卩密口定 -7 -酮。 6 .如申請專利範圍第1項之化合物，係用作治療或 預防c G Μ P P D Ε 5抑制劑所適應醫學病症之人類醫 藥品。 ' 7 .如申請專利範圍第1項之化合物，係用作治療或 預防c G Μ P P D Ε 5抑制劑所適應醫學病症之動物醫 藥品。 8 .如申請專利範圍第1項之化合物，係用於製造一 種用來治療或預防c G Μ P P D Ε 5抑制劑所適應醫學 病症之人類醫藥品。 經濟部智慧財產局員工消費合作社印製 9 .如申請專利範圍第1項之化合物，係用於製造一 種用來治療或預防c G Μ P P D Ε 5抑制劑所適應醫學 病症之動物醫藥品。 1 〇 .如申請專利範圍第6或8項之化合物，其中該 醫學病症爲雄性勃起官能障礙，雌性性官能障礙，早產， 痛經，良性攝護腺肥大（Β Ρ Η )，膀胱出口阻塞，失禁 ，穩定性，不穩定性與各種（Prinzmetal)絞痛，高血壓， 肺高血壓，充血性心臟衰竭，動脈硬化，中風，末稍血管 疾病，減少血管開放的病症，慢性氣喘，支氣管炎，過敏 本纸張尺度適用中國國家標準（CNS ) A4規格（210X297公釐） -6 - 524805 A8 B8 C8 D8 六、申請專利範圍 性氣喘，過敏性鼻炎，青光眼，以及以腸能動性失調爲特 徵之疾病。 1 1 ·如申請專利範圍第7或9項之化合物，其中該 醫學病症爲雄性勃起官能障礙，雌性性官能障礙，早產， 痛經，良性攝護腺肥大（B P Η )，膀胱出口阻塞，失禁 ，穩定性，不穩定性與各種（Prinzmetal )絞痛，高血壓， 肺高血壓，充血性心臟衰竭，動脈硬化，中風，末稍血管 疾病，減少血管開放的病症，慢性氣喘，支氣管炎，過敏 性氣喘，過敏性鼻炎，青光眼，以及以腸能動性失調爲特 徵之疾病。 12·—種用於治療或預防人類cGMP PDE5 抑制劑所適應醫學病症之藥學組合物，包括如申請專利範 圍第1項之化合物或其藥學上可接受之鹽類以及一種藥學 上可接受之稀釋劑或載體。 1 3 · —種用於治療或預防c G Μ P P D Ε 5抑制 劑所適應醫學病症之獸醫組合物，包括如申請專利範圍第 1項之化合物或其獸醫學上可接受之鹽類以及一種獸醫學 上可接受之稀釋劑或載體。 1 4 ·如申請專利範圍第1 2項之藥學組合物或如申 請專利範圍第1 3項之獸醫組合物，·係用於治瘴或預防哺 乳動物（包括人類）雄性勃起官能障礙，雌性性官能障礙 ，早產，痛經，良性攝護腺肥大（Β Ρ Η )，膀胱出口阻 塞，失禁，穩定性，不穩定性與各種（Prinzmetal )絞痛， 高血壓，肺高血壓，充血性心臟衰竭，動脈硬化，中風， 本紙張尺度適用中國國家標準（CNS ) A4規格（210X297公釐） -7 - (請先閱讀背面之注意事項再填寫本頁) -裝· 訂 經濟部智慧財產局員工消費合作社印製 524805 A8 B8 C8 D8 六、申請專利範圍 末稍血管疾病，減少血管開放的病症，慢性氣喘，支氣管 炎，過敏性氣喘，過敏性鼻炎，青光眼，以及以腸能動性 失調爲特徵之疾病等病症。 15 · —種如式（ΠΑ)或（ΠΒ)之化合物(Please read the notes on the back before filling this page) (IA) (IB) or its pharmaceutically or veterinarily acceptable salts, where R1 is Ci—C3 alkyl, (CH2) nHet or (CH 2 ) n A r, wherein the C i -C 3 alkyl is substituted by C 3 -C 6 cycloalkyl, CONR 5 R 6 or N-linked heterocyclic group, the heterocyclic group is selected from Pyrazolyl, triazolyl, morpholinyl and 4-R 9 -hexahydropyridyl; printed by the Consumer Cooperatives of the Intellectual Property Bureau of the Ministry of Economic Affairs R 2 is C i — C 6 alkyl R 3 is selective via ci C 1 —C 1 5 alkyl substituted by a C ′ 4 alkoxy group; R 4 is S 〇 2 NR 7 R 8 · JR 5 is Η; R 6 is optionally substituted by C i — C 4 alkoxy Substituted C i -C 4 fluorenyl group, or R 5 and R 6 together with the nitrogen atom connected to it to form a morpholinyl group; This paper size applies the Chinese National Standard (CNS) A4 specification (210X297 mm 524805 A8 B8 C8 D8 Six 2. The scope of patent application: R7 and R8 together with the nitrogen atom connected to it form 4—R1C) -hexahydropyridyl; R9 is Ci—〇4 焼 group; R 1 ◦ is Η or optionally through Η, C! —C 4 alkoxy or CON Η 2 substituted C! —C 4 alkyl; H et is selected from pyridyl, 1-oxypyridyl (Ιο X id 〇pyridiny 1), 1 sulfonyl group, Pyrimidinyl, pyridoxyl, misoyl, isoxazolyl, thiazolyl, triazolyl, and oxadiazolyl, each of which can be selectively selected from one or two by C 1- C 4 radical (optionally substituted by C 1 -C 4 radical), Ci — C 4 alkoxy and NH22 substituent JA r is optionally selected by one or two selected from C χ — C 4 Alkyl, Ci-C4 alkoxy, halo, CN, CONH2, No02, NH2, NHS02 (Ci-C, alkyl) and phenyl substituted with a substituent of SO2NH2; And η is ◦ or 1. 2. The compound according to item 1 of the scope of patent application, wherein R 1 is a heterocyclic group (selected from pyrazolyl, triazolyl, morpholinyl, and pyrazolyl, triazolyl, and morpholinyl) connected through C3-C5 cycloalkyl, CONR5R6, or N- 4—R 9 -hexahydropyridinyl) Cl—C2 courtyard substituted; (CH2) nHe t or (CH 2) n A r; R 5 is Η and R 6 is selective via C! — C 4 C C4 alkyl substituted by alkoxy or R5 and R6 together with the nitrogen atom to which they are attached form a morpholinyl; Het is selected from pyridyl, 1-oxidopyddinyl, daphnyl, pyrimidinyl The basic paper size of Pyridoxine and Imidazole is applicable to the Chinese National Standard (CNS) M specification (210X297 mm) -2-(Please read the precautions on the back before filling this page) • Binding-LP Intellectual Property of the Ministry of Economic Affairs Printed by the Bureau's Consumer Cooperatives 524805 A8 B8 C8 --------__ VI. Applying for Temple Pass ~~ "-, isoxazolyl, thiazolyl, triazolyl, and oxadiazolyl, and Either can be optionally substituted with one or two substituents selected from CH3, CH2CH2, oCH3, oCH3 and NH2; and r2, r3 r 4 (Please read the notes on the back before filling (This page) R 9, A r and n are as defined in item 丄 of the patent application. 3 _ As for the compound in the scope of patent application item 2, wherein R: is cyclobutyl, CONR5R6, pyrazol-1-yl, 1,2,3-trimile-1, 1,2,4 —Triazole—1-yl, morpholine—4-yl, or 4-methylhexahydropyridine—1-yl substituted by 1—c 2 alkyl; pyrimidine D—2-yl; CH2He t or (CH2) ηAl ·; R2 is a C 3 alkyl group; R 3 is a C i -C 3 alkyl group optionally substituted with a C i-C 2 alkoxy group; R 5 is Η and R 6 is a selective A C C2 alkyl group substituted by c 1 -C 2 alkoxy or R 5 and R 6 together with the nitrogen atom attached thereto forms a morpholine 4 1 group; R 1. For selective C i -C 2 alkyl substituted with 〇η, 〇C Η 3 or CON Η 2; Het is selected from 2-pyridine printed by the consumer co-operative of the Intellectual Property Bureau of the Ministry of Economic Affairs —Oxypyridine—2-yl, pyridine—3-yl, dagen—3-yl, daxy—4-yl, pyrimidine — 4-yl, pyrimidine — 5-yl, orbiphine — 2-yl, 3 — Methoxy d is more than n-di-2-yl, 6-amino 13 is more than 2-diyl, 1-methylimidazol-2-yl, 3,5-dimethylisoxazol-4-yl, 2 —Methylthiazole-4-yl, 1-methyl-1, 2, 4-triazol-5-yl, 1— (2-methoxyethyl) —1,2,4-triazol-5-yl , 4-methyl-1,2,4-triazol-3-yl, 3-methyl-1,2,4-triazol-5-yl, 1,2,4-oxadiazol-3-yl And 5-methyl-1,2,4 crocodizole 3-yl; Αχ * is selected from phenyl, 4-chlorochloro, 4-bromophenyl, 2-cyanobenzene. The paper size is applicable to China. Standard (CNS) Α4 Specification (210 X 297 mm) -3-Printed by the Consumer Consumption Cooperative of the Intellectual Property Bureau of the Ministry of Economy 524805 A8 B8 C8 _ D8 VI. Patent application scope, 2-aminocarbonylphenyl, 4-monoaminocarbonylphenyl, 2-nitrophenyl, 4-mononitrophenyl, 2-aminophenyl, 4-monoaminophenyl, 2-methanesulfonyl phenyl, 4-methanesulfonyl phenyl, 4-monoethanesulfonyl phenyl, 4-mono (propyl ~ 2-sulfonamido) phenyl, and 4-monosulfanil And η is as defined in item 2 of the scope of patent application. 4 · The compound according to item 3 of the scope of patent application, wherein R 1 is cyclobutylmethyl, morphine-4 monomethyl, 2- (morpholin-4 4-yl) ethyl, pyrimidine-2-yl, CH2He t or (CH2) nAr; R2 is CH2CH3 or CH2CH2CH3; R3 is CH2CH3, CH2CH2CH3 or CH2CH2〇CH3; R10 is ch3, CH2CH3 or CH2CH2〇H; He t is selected from pyridin 2- 2-yl, dagen-3-yl , Pycnogenol 2-yl, 3-methoxypyridine 2-yl, 6-aminopyridine-2-yl, 1-methylimidazol-2-yl, 3, 5-dimethylisoxazole- 4- Methyl, 1-methyl-1,2,4-triazole ~ 5-yl, 1- (2-methoxyethyl) -1,2,4-triazole-5-yl and 5-methyl-1 , 2,4-oxadiazol_3-yl; Ar is selected from phenyl, 2-aminephenyl, 2-methanesulfonamidophenyl, 4-methanesulfonamidophenyl, 4-ethanesulfonyl Amidinophenyl and 4-mono (propan-2-ylsulfonamido) phenyl; and η is as defined in item 3 of the scope of patent application. 5. The compound according to item 4 of the scope of patent application, wherein the compound of the formula (IA) or (IB) is selected from the group consisting of 5-{5-[4-(2-Xiang ethyl) six gas roar-1 1 Sulfofluorenyl]-2 -n-propoxyphenyl 丨-3-n-propyl-1-(pyridine --------------- Order ------ 9 (Please Please read the notes on the back before filling this page) This paper size is applicable to Chinese National Standard (CNS) A4 specification (210X297mm) -4-524805 A8 B8 C8 D8 hole, patent application scope 1 2-base) methyl-1 , 6-dihydro-7Η-pyrazolo [4,3-d] pyrimidine-7-one; (Please read the precautions on the reverse side before filling out this page) 1— (1 methylimidazol-2 —Yl) methyl 5 — [5 — (4-methylhexahydropyridine 1-ylsulfonyl) —2-n-propoxyphenyl] 3—n-propyl-1,6-dihydro —7H —pyrazolo [4,3 -d] pyridamidine-7-one; 5 — {5 — [4 — (2-hydroxyethyl) hexahydropyridine-1 1-ylsulfonyl]] 2 -n-propoxyphenyl 丨 -3 -n-propyl-2- (pyridine-2-yl) methyl-2,6-di —7H —pyrazolo [4, · 3 —d] pyrimidin-7—one; 5-[5 — (4-ethylhexahydropyridine—1 monosulfonyl) — 2 —n-dioxo Phenyl] -3 -n-propyl-2-(D than hydradin-2-yl) methyl -2,6-dihydro-7 hydrazone -pyrazolo [4,3-d] pyrimidin-7-one Printed by the Consumer Cooperatives of the Intellectual Property Bureau of the Ministry of Economic Affairs 3 -Ethyl-5-[5-(4-Ethylhexahydropyridine-1 -sulfosulfanyl)-2-n-propoxyphenyl]-2- (Pyridine-2-yl) methyl-2,6-dihydro-7 pyrene-pyrazolo [4,3-d] pyrimidin-7-one; 5-[5-(4 -ethylhexahydropyridine) -1-1-sulfofluorenyl)-2 -n-propoxyphenyl]-3-n-propyl-2-(daquinone 3 -yl) methyl-2, 6-dihydro-7 fluorene-pyrazolo [4,3-d] pyrimidin-7.-one; 5-[5-(4-monoethylhexahydropyridine-1 -ylsulfofluorenyl)-2 -n-propoxyphenyl] -3 -n-propyl Base 1 2-(Tower Coupling-2-Base) The paper size applies to the Chinese National Standard (CNS) A4 specification (210X297 mm) -5-524805 A8 B8 C8 D8 Six The scope of patent application is methyl-2,6-dihydro-7H-pyrazolo [4, 3-d] pyrimidin-7-one; and (please read the precautions on the back before filling this page) 5 — [2— Ethoxy-5— (4-ethylhexahydro d than phen-1—1-sulfofluorenyl) phenyl] —3—n-propyl-2— (pyridine—2-yl) —methyl-2,6— Diamino-7H-D sits more than [4,3 — d] cylopidine-7-one. 6. The compound according to item 1 of the scope of patent application is a human medicine for treating or preventing a medical condition to which a c G MP P D E 5 inhibitor is adapted. '7. The compound according to item 1 of the scope of patent application is an animal medicine for treating or preventing a medical condition to which a c G MP P D E 5 inhibitor is adapted. 8. The compound according to item 1 of the scope of patent application is for the manufacture of a human pharmaceutical for treating or preventing a medical condition to which a cG MP P D E 5 inhibitor is adapted. Printed by the Consumer Cooperative of the Intellectual Property Bureau of the Ministry of Economic Affairs 9. The compound in the scope of patent application No. 1 is used for the manufacture of an animal medicine for treating or preventing a medical condition to which the c G MP P D E 5 inhibitor is applied. 10. The compound of claim 6 or 8, wherein the medical condition is male erectile dysfunction, female dysfunction, premature birth, dysmenorrhea, benign prostatic hypertrophy (ΒΡΗ), bladder outlet obstruction, incontinence , Stability, instability and various (Prinzmetal) colic, hypertension, pulmonary hypertension, congestive heart failure, arteriosclerosis, stroke, terminal vascular disease, reduced vascular openness, chronic asthma, bronchitis, allergies This paper size applies to the Chinese National Standard (CNS) A4 specification (210X297 mm) -6-524805 A8 B8 C8 D8 6. Application for patent scope asthma, allergic rhinitis, glaucoma, and diseases characterized by intestinal motility disorders. 1 1 · The compound according to item 7 or 9 of the scope of patent application, wherein the medical condition is male erectile dysfunction, female dysfunction, premature birth, dysmenorrhea, benign prostate hypertrophy (BP Η), bladder outlet obstruction, incontinence, Stability, instability and various (Prinzmetal) colic, hypertension, pulmonary hypertension, congestive heart failure, arteriosclerosis, stroke, terminal vascular disease, conditions that reduce vascular opening, chronic asthma, bronchitis, allergies Asthma, allergic rhinitis, glaucoma, and diseases characterized by intestinal motility disorders. 12 · —A pharmaceutical composition for treating or preventing a medical condition to which a human cGMP PDE5 inhibitor is adapted, including, for example, a compound or a pharmaceutically acceptable salt thereof as claimed in the first patent application scope, and a pharmaceutically acceptable dilution Agent or carrier. 1 3 · A veterinary composition for treating or preventing a medical condition to which a c G M PPD E 5 inhibitor is adapted, including, for example, a compound of the scope of patent application or its veterinarily acceptable salt and a veterinary Medically acceptable diluents or carriers. 14 · The pharmaceutical composition as claimed in item 12 or the veterinary composition as claimed in item 13 in the patent application, is used to cure or prevent male erectile dysfunction in mammals (including humans), and female sex Dysfunction, premature birth, dysmenorrhea, benign prostatic hypertrophy (ΒΡΗ), bladder outlet obstruction, incontinence, stability, instability and various (Prinzmetal) colic, hypertension, pulmonary hypertension, congestive heart failure, Arteriosclerosis, stroke, this paper size applies Chinese National Standard (CNS) A4 specification (210X297 mm) -7-(Please read the precautions on the back before filling out this page) Printed 524805 A8 B8 C8 D8 Sixth, the scope of the patent application is at the end of the vascular disease, reducing vascular openness, chronic asthma, bronchitis, allergic asthma, allergic rhinitis, glaucoma, and diseases characterized by intestinal motility disorders. . 15 · a compound such as formula (ΠΑ) or (ΠΒ) 丫Ya R so, (ΠΒ) (請先閲讀背面之注意事項再填寫本頁) 裝· ΠΙΑ) 其中Υ爲鹵基，而R 1，R 2與R 3係如申請專利範圍第1 項中所定義者。 1 6 ·如申請專利範圍第1 5項之化合物，其中Y爲 氯。 17 · —種如式（IVA)或（IVB)之化合物 訂 經濟部智慧財產局員工消費合作社印製R so, (ΠΒ) (Please read the precautions on the back before filling out this page) ΠΙΑ) where Υ is a halogen group, and R 1, R 2 and R 3 are as defined in item 1 of the scope of patent application . 16 · The compound according to item 15 in the scope of patent application, wherein Y is chlorine. 17 · — A compound such as formula (IVA) or (IVB) Order Printed by the Consumer Cooperative of the Intellectual Property Bureau of the Ministry of Economic Affairs R3〇R3〇 〇 R2 (JVB) 其中R 1，R 2與R 3係如申請專利範圍第1項中所定義者 8 · —種如式（IX A )或（K B )之化合物 本紙張尺度適用中國國家標準（CNS ) A4規格（210X297公釐） -8 - 524805 A8 B8 C8 D8 六、申請專利範圍〇R2 (JVB) where R 1, R 2 and R 3 are as defined in item 1 of the scope of the patent application 8-a compound such as formula (IX A) or (KB) The paper size applies Chinese national standards ( CNS) A4 specification (210X297 mm) -8-524805 A8 B8 C8 D8 6. Application scope 其中R 1，R 2，R 3與R 4係如申請專利範圍第1項中所定 義者。 1 9 . 一種用於製備如申請專利範圍第1項化合物之 方法， 包括分別令式（Π A )或（Π B )化合物與式（m ) 化合物反應， (請先閱讀背面之注意事項再填寫本頁) .裝·Among them, R 1, R 2, R 3 and R 4 are as defined in item 1 of the scope of patent application. 19. A method for preparing a compound as described in the first patent application, which comprises reacting a compound of formula (ΠA) or (ΠB) with a compound of formula (m), respectively, (please read the notes on the back before filling (This page). NN R I N B)R I N B) 經濟部智慧財產局員工消費合作社印製 (其中Y爲鹵基，而R 1，R 2與R 3係如申請專利範圍第 1項所定義者） . R 7 R 8 N H ( m ) (其中R 7與R 8係如申請專利範圍第1項中所定義者） 本紙張尺度適用中國國家標準（CNS ) A4規格（210X297公釐） -9 - 524805Printed by the Consumer Cooperatives of the Intellectual Property Bureau of the Ministry of Economic Affairs (where Y is a halogen group, and R 1, R 2 and R 3 are as defined in item 1 of the scope of patent application). R 7 R 8 NH (m) (where R 7 and R 8 are as defined in item 1 of the scope of patent application) This paper size applies to the Chinese National Standard (CNS) A4 specification (210X297 mm) -9-524805 N — R1 •裝· A8 B8 C8 D8 、申請專利範圍 其後可選擇性形成所需產物的藥學上或獸醫學上可接受之 鹽類。 2 0 . —種用於製備如申請專利範圍第1項化合物之 方法，包括分別令式（K A )或（K B )化合物環化N — R1 • Equipment • A8 B8 C8 D8, scope of patent application. After that, it can selectively form the pharmaceutically or veterinarily acceptable salts of the desired product. 2 0. A method for preparing a compound as claimed in the first scope of the patent application, comprising cyclizing a compound of formula (K A) or (K B), respectively (其中R 1，R 2，R 3與R 4係如申請專利範圍第1項中所 定義者） 其後可選擇性形成所需產物的藥學上或獸醫學上可接受之 鹽類。 (請先閱讀背面之注意事項再填寫本頁) 、言 經濟部智慧財產局員工消費合作社印製 本紙張尺度適用中國國家標準（CNS ) A4規格（210 X 297公釐） 10-(Wherein R 1, R 2, R 3 and R 4 are as defined in item 1 of the scope of patent application). Thereafter, pharmaceutically or veterinarily acceptable salts can be selectively formed into desired products. (Please read the precautions on the back before filling out this page). Language: Printed by the Consumer Cooperatives of the Intellectual Property Bureau of the Ministry of Economic Affairs. The paper size is applicable to China National Standard (CNS) A4 (210 X 297 mm).
TW87102657A 1997-04-25 1998-02-24 Pyrazolo[4,3-d]pyrimidine-7-one compounds having the effect of inhibiting phosphodiesterase (PDE-5) and the preparation processes, intermediates and pharmaceutical compositions or veterinary formulations thereof TW524805B (en)

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GBGB9708406.5A GB9708406D0 (en) 1997-04-25 1997-04-25 Therapeutic agents
GBGB9722954.6A GB9722954D0 (en) 1997-10-30 1997-10-30 Therapeutic agents

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