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1、TheprofessionalEnglishofpharmaceuticalengineeringWang XinliangEast China university of science and technology13.02.2012第一页，共81页。vFinalexaminationTwoparts:gradeofdailystudy(30%)attendanceratehomeworkothers(exercise,middleexamination)gradeoffinalexamination(70%)Thecontentofexamination第二页，共81页。Theconte
2、ntofexaminationvDegreetest50%basicEnglish50%professionalEnglishword:translationfromEnglishtoChinese(5points)translationfromChinesetoEnglish(5points)Translation:(40points)4paragraphswhichincludeabout250wordsineachofthem.payattentiontoonly125to150wordsineachparagraphneedtobetranslated.These4paragraphs
3、arenotsimplesentence.第三页，共81页。HowtolearntheprofessionalEnglishvMastersomeskillsvMasterthenecessaryknowledgevWhatisthemostimportantthing第四页，共81页。vWhatistheimportantthinginthiscoursevremembertheword?vtranslatesentencebysentence?vlearnmoreprofessionalknowledge?vYoudaoDict有道有道(yudo)词典词典Howtoteachtheprof
4、essionalEnglish第五页，共81页。Crocinyellow（藏花素）（藏花素）,whichisextractedfromGardeniajasminoidesEllis（栀子（栀子(zhz)）,iswidelyusedasanaturalfoodcolorantinAsiancountries,whileGardeniaextracthasbeenusedinChinesetraditionalmedicine(CTM)forcuringanumberofailments3.Thesecrocetin（藏红花酸）（藏红花酸）derivatives,whicharedifferen
5、tfrommostfamiliesofcarotenoids（类胡萝卜素）（类胡萝卜素）,areknownfortheircoloringpropertiesowingtotheirpeculiarwater-solublebehavior4.Numerousstudieshavedealtwiththecomponentstructuresofyellowpigmentextractsisolatedfromgardeniafruits48,theirspectroscopiccharacterizationandradical-scavengingactivity4,9,dataconce
6、rningtheconcentrationofmajorcomponentsforthedeterminationofoptimaltimeofharvestandextractionprocess10,11.第六页，共81页。ThecontentofthiscoursevIntroducesomeskillsoftranslationanddosomeexerciseintheclassroom.vSummarizesomeregulationsintheprofessionalEnglish.vLearnthetext.vDiscusssometopics.第七页，共81页。Part1Me
7、dicinalchemistryUnit1ProductionofDrugsvThewholeconceptoftheproductionofdrugsvTheclassificationofthedrugsvTheintroductionofeachgroupofdrugs第八页，共81页。Thefirstquestion:howtoclassifythedrugvDependingonthekindsofdisease:CardiovasculardrugsDigestivesystemdrugsRespiratorysystemdrugsAntiviraldrugsvProprietar
8、ydrugsorGenericdrugsvDependingontheproductionororigin:第九页，共81页。药品的生产药品的生产依据其生产或来源，药物制剂可以分为三类：依据其生产或来源，药物制剂可以分为三类：I.I.完全的合成材料（人工合成材料），完全的合成材料（人工合成材料），II.II.天然天然(tinrn)(tinrn)产物，和产物，和III.III.源自部分合成的产品（半合成产品）。源自部分合成的产品（半合成产品）。Depending on their production or origin pharmaceutical agents can be split in
9、to three groups:I.Totally synthetic materials(synthetics)，II.Natural products，andIII.Products from partial syntheses(semi-synthetic products).Unit1ProductsofDrugs第十页，共81页。Wordssyntheticsglycoside(s)hydrolysatedextrantargetedmodificationEpinephrineLevodopaProstaglandinsD-PenicillamineVincamineEukaryo
10、ntProkaryontLeuconostoc mesenteroidesCorynebacterium glutamicumBrevibacteriumflavumPropionibacterium shermaniipurinanucleotidecitricacidmonosodiumL-glutamatechromatinn.用作复用作复人工合成人工合成(绝缘绝缘)材料材料n.配醣；配糖体；糖苷配醣；配糖体；糖苷n.水解液；水解产物水解液；水解产物n.葡萄葡萄(pto)聚糖；右旋糖酐聚糖；右旋糖酐定向（或靶向）修饰定向（或靶向）修饰n.肾上腺素肾上腺素n.药药左旋多巴（等于左旋多巴（等
11、于L-dopa）n.前列腺素（前列腺素（prostaglandin的复数形式）的复数形式）n.D-青霉胺青霉胺n.长春胺长春胺n.真核细胞真核细胞n.原核细胞原核细胞肠膜状明串珠菌肠膜状明串珠菌谷氨酸棒杆菌谷氨酸棒杆菌黄色短杆菌黄色短杆菌谢氏丙酸杆菌谢氏丙酸杆菌嘌呤核苷（酸）嘌呤核苷（酸）柠檬酸柠檬酸谷氨酸钠（味精）谷氨酸钠（味精）n.核染色质；核染质核染色质；核染质第十一页，共81页。AlkalimetalLilithiumNasodiumKpotassiumRbrubidiumCscaesiumFrfranciumHhydrogen第十二页，共81页。本本书的重点是在于的重点是在于和和类中
12、最重要的化合物中最重要的化合物药物合成。但是，物合成。但是，这并不意味着，并不意味着，天然天然产品或其他制品或其他制剂并不太重要。它并不太重要。它们可以可以(ky)作作为有价有价值的先的先导结构，他构，他们常常作常常作为重要的合成重要的合成产品的起始原料或中品的起始原料或中间体体产品。品。表表1列出了列出了获取取药物制物制剂的不同方法的概述。的不同方法的概述。The emphasis of the present book is on the most important compounds of groups I and -thus Drug synthesis.This does not
13、mean，however，that natural products or other agents are less important.They can serve as valuable lead structures，and they are frequently needed as starting materials or as intermediates for important synthetic products.Table 1 gives an overview of the different methods for obtaining pharmaceutical a
14、gents.第十三页，共81页。最初从天然最初从天然资源源库获得的几个重要治得的几个重要治疗作用的天然作用的天然产品，今天品，今天可以通可以通过全合成更有效地，例如更全合成更有效地，例如更经济地被制地被制备(zhbi)出来。出来。这样的例子包括的例子包括L-氨基酸、氨基酸、氯霉素、咖啡因、多巴胺、霉素、咖啡因、多巴胺、肾上腺素、上腺素、左旋多巴、左旋多巴、肽类激素、前列腺素、激素、前列腺素、D-青霉胺、青霉胺、长春胺，以及几乎春胺，以及几乎所有的所有的维生素。生素。Several therapeutically significant natural products which were o
15、riginally obtained from natural sources are today more effectively-i.e.more economically-prepared by total synthesis.Such examples include L-amino acids,Chloramphenicol,Caffeine,Dopamine,Epinephrine,Levodopa,peptide hormones,Prostaglandins,D-Penicillamine,Vincamine,and practically all vitamins.第十四页，
16、共81页。在过去的几年里，发酵在过去的几年里，发酵(fjio)，即微生物过程，变得极其重要。通过，即微生物过程，变得极其重要。通过现代技术和基因选择导致的微生物的高性能突异变种的结果，发酵现代技术和基因选择导致的微生物的高性能突异变种的结果，发酵(fjio)已成为选择宽范围物质的方法。真核细胞（酵母菌和霉菌）和原核细已成为选择宽范围物质的方法。真核细胞（酵母菌和霉菌）和原核细胞（单细胞细菌，放线菌）都可用作微生物。可以得到下列产品类型：胞（单细胞细菌，放线菌）都可用作微生物。可以得到下列产品类型：Over the last few years fermentation-i.e.microbio
17、logical processes has become extremely important.Through modern technology and results from genetic selection leading to the creation of high performance mutants of microorganisms,fermentation has already become the method of choice for a wide range of substances.Both Eukaryonts(yeasts and moulds)an
18、d Prokaryonts(single bacterial cells,and actinomycetes)are used microorganisms.The following product types can be obtained:第十五页，共81页。尽管从诸如肠膜状明串球菌的某些微生物的黏膜可以生产葡萄聚糖，但尽管从诸如肠膜状明串球菌的某些微生物的黏膜可以生产葡萄聚糖，但第第2和和3类产品类型只与药品生产的有关。葡聚糖自身的分子量类产品类型只与药品生产的有关。葡聚糖自身的分子量5万万10万，万，可用作血浆代用品。而来自谷氨酸棒杆菌和黄色短杆菌突变体的初级代谢产可用作血浆代用品。
19、而来自谷氨酸棒杆菌和黄色短杆菌突变体的初级代谢产物中，物中，L-氨基酸尤其令人感兴趣。从这些生物体中，可以生产约氨基酸尤其令人感兴趣。从这些生物体中，可以生产约35万吨万吨L-谷谷氨酸单钠盐（味精，食品添加剂）和约氨酸单钠盐（味精，食品添加剂）和约70,000吨吨L-赖氨酸（用于植物蛋白补赖氨酸（用于植物蛋白补充物质）。此外，重要的初级代谢产物还有嘌呤充物质）。此外，重要的初级代谢产物还有嘌呤(piolng)核苷酸、有机酸、核苷酸、有机酸、乳酸、柠檬酸和维生素，例如源自谢氏丙酸杆菌的维生素乳酸、柠檬酸和维生素，例如源自谢氏丙酸杆菌的维生素B12。Disregarding the product
20、ion of dextran from the mucous membranes of certain microorganisms，e.g.Leuconostoc mesenteroides,classes 2 and 3 are the relevant ones for the preparation of drugs.Dextran itself,with a molecular weight of 50,000 100,000,is used as a blood plasma substitute.Among the primary metabolites the L-amino
21、acids from mutants of Corynebacterium glutamicum and Brevibacterium flavum are especially interesting.From these organisms some 350,000 tones of monosodium L-glutamate(food additive)and some 70,000 tones of L-lysine(supplement for vegetable proteins)are produced.Further important primary metabolites
22、 are the purina nucleotides,organic acids,lactic acid,citric acid,and vitamins,for example vitamin B12 from Propionibacterium shermanii.第十六页，共81页。在次生代谢产物中首先必须提到的是抗生素。以下五组药品代表了全球每在次生代谢产物中首先必须提到的是抗生素。以下五组药品代表了全球每年年(minin)价值价值170亿美元：亿美元：青霉素类（产黄青霉），青霉素类（产黄青霉），头孢菌素类（顶头孢霉菌），头孢菌素类（顶头孢霉菌），四环素类（金霉素链霉菌），四环素类（
23、金霉素链霉菌），红霉素类（红霉素链霉菌），红霉素类（红霉素链霉菌），氨基糖苷（如来自灰色链霉菌的链霉素）。氨基糖苷（如来自灰色链霉菌的链霉素）。Among the secondary metabolites the antibiotics must be mentioned first.The following five groups represent a yearly worldwide value of US-$17 billion:penicillins (Penicillium chrysogenum)，cephalosporins(Cephalosporium acremoniu
24、m)，tetracyclines(Streptomyces aureofaciens)，erythromycins(Streptomyces erythreus)，aminoglycosides(e.g.streptomycin from Streptomyces griseus).第十七页，共81页。Dextran is a polymer of glucose.It is a white powder and it is soluble in water and insoluble in ethanol.Dextran can increase the plasma volume and
25、maintain the blood pressure,so it can be used for as a blood plasma substitute.It can be produced by fermentation of sucrose in leuconostoc mesenteroides.Certainly,the fermentation only produce the raw material and the some purification is necessary.ThesimpleintroductionofdextranMolecularformula:（C6
26、H10O5）nglucose葡萄糖葡萄糖fructose果糖果糖(gutng)mono-,di-,tri-,polymer单体单体(dn t)，二聚体，三聚体，聚合体，二聚体，三聚体，聚合体(物物)sucrose n.蔗糖蔗糖(zhtng)第十八页，共81页。从微生物中已分离出约从微生物中已分离出约5000种抗生素，但其中只有不到种抗生素，但其中只有不到100种有治疗用途。但是，种有治疗用途。但是，必须记住，许多衍生物已通过部分合成法来修饰以获得治疗用途；在过去的十年里，采必须记住，许多衍生物已通过部分合成法来修饰以获得治疗用途；在过去的十年里，采用半合成方法用半合成方法(fngf)已从已从-
27、内酰胺获得了约内酰胺获得了约50,000种制剂。发酵是在体积高达种制剂。发酵是在体积高达400m3的不锈钢发酵罐中进行。为了避免受到噬菌体等微生物的污染，（发酵）全过程都必须的不锈钢发酵罐中进行。为了避免受到噬菌体等微生物的污染，（发酵）全过程都必须在无菌条件下进行。由于更重要的是，发酵只在有氧条件下才能发生；因此，需要提供在无菌条件下进行。由于更重要的是，发酵只在有氧条件下才能发生；因此，需要提供有足够量的（无菌）氧气或空气。二氧化碳的来源包括糖类（碳水化合物），如废糖浆、有足够量的（无菌）氧气或空气。二氧化碳的来源包括糖类（碳水化合物），如废糖浆、低聚糖类和葡萄糖。低聚糖类和葡萄糖。Abo
28、ut 5000 antibiotics have already been isolated from microorganisms,but of these only somewhat fewer than 100 are in therapeutic use.It must be remembered，however，that many derivatives have been modified by partial synthesis for therapeutic use;some 50,000 agents have been semisynthetically obtained
29、from-lactams alone in the last decade.Fermentations are carried out in stainless steel fermentors with volumes up to 400 m3.To avoid contamination of the microorganisms with phages etc.the whole process has to be performed under sterile conditions.Since the more important fermentations occur exclusi
30、vely under aerobic conditions,a good supply of oxygen or air(sterile)is needed.Carbon dioxide sources include carbohydrates,e.g.molasses,saccharides,and glucose.第十九页，共81页。Wordsammonium（ammonia）aminesodiumbicarbonatesodiumhydroxidehydrochloric/sulfuric/nitricacidhypochloritechloritechlorateperchlorat
31、enitritenitratesulfidesulfitesulfatepersulfatephosphitehypophosphitephosphatedihydrogenphosphatehydrogenphosphate铵；铵盐铵；铵盐（氨；氨水）（氨；氨水）胺胺碳酸氢钠；小苏打、碳酸氢钠；小苏打、NaHCO3氢氧化钠氢氧化钠、NaOH盐酸；硫酸盐酸；硫酸(lisun)；硝酸；硝酸次氯酸盐（酯）次氯酸盐（酯）亚氯酸盐（酯）亚氯酸盐（酯）氯酸盐（酯）氯酸盐（酯）高氯酸盐（酯）高氯酸盐（酯）亚硝酸盐（酯）亚硝酸盐（酯）硝酸盐（酯）硝酸盐（酯）硫化物；硫醚硫化物；硫醚亚硫酸亚硫酸(lisun)
32、盐（酯）盐（酯）硫酸硫酸(lisun)盐（酯）盐（酯）过硫酸过硫酸(lisun)盐（酯）盐（酯）亚磷酸盐（酯）亚磷酸盐（酯）次磷酸盐（酯）次磷酸盐（酯）磷酸盐（酯）磷酸盐（酯）磷酸二氢盐磷酸二氢盐磷酸一氢盐磷酸一氢盐第二十页，共81页。Prefix-Parent-SuffixNomenclatureofparentpart:NomenclatureofalkanesandalkylsubstituentsStraight-chainalkanesStraight-chainalkanesarenamedbycountingthenumberofcarbonatomsinthechainanda
33、ddingthefamilysuffix-ane.Thuspentaneisthefive-carbonalkane,andhexaneisthesix-carbonalkane.NomenclatureofOrganicCompounds1第二十一页，共81页。vAn alkyl substituent(or an alkyl group)is an alkane from which a single hydrogen has been removed.vAlkyl substituents are named by replacing the“ane”suffix of the alka
34、ne with“yl”.The letter“R”is used to indicate any alkyl group.vThus CH3-has the name of methyl,while the group of CH3CH2-was named ethyl.第二十二页，共81页。NumberMolecularNameNameinAlkylofcarbonsformulaChinesesubstituents1CH4Methane甲烷甲烷Methyl2C2H6Ethane乙烷乙烷Ethyl3C3H8Propane丙烷丙烷Propyl4C4H10Butane丁烷丁烷Butyl5C5H
35、12Pentane 戊烷戊烷Pentyl6C6H14Hexane己烷己烷Hexyl7C7H16Heptane庚烷庚烷Heptyl8C8H18Octane辛烷辛烷Octyl9C9H20Nonane壬烷壬烷Nonyl10C10H22Decane癸烷癸烷Decyl11C11H24Undecane十一十一(ShY)烷烷Undecyl12C12H26Dodecane十二烷十二烷Dodecyl13C13H28Tridecane十三烷十三烷Tridecyl20C20H42Icosane二十烷二十烷Icosyl21C21H44Heneicosane二十一二十一(ShY)烷烷Heneicosyl30C30H62
36、Triacontane三十烷三十烷Triacontyl第二十三页，共81页。Branched-chainalkanes3-ethyl-3-methylhexane第二十四页，共81页。SomeusefulprefixesforindicatingthenumberofsubstituentgroupsMono-单取代单取代(qdi),一取代一取代(qdi)Di-二取代二取代(qdi)Tri-三取代三取代(qdi)Tetra-四取代四取代(qdi)Pent(a)-五取代五取代(qdi)Hex(a)-六取代六取代(qdi)Hept(a)-七取代七取代(qdi)Oct(a)-八取代八取代(qdi)N
37、ona-九取代九取代(qdi)Deca-十取代十取代(qdi)2,6-dimethyloctanenot2-ethyl-6-methylheptane3-ethyl-2-methylhexanenot3-isopropylhexane第二十五页，共81页。vSomeusefulprefixesusedtonamebranchedalkanes(Commonnames)(normal)n-正正(isomer)iso-异异neo-新新primary 伯，一级伯，一级(secondary)sec-仲，二级仲，二级(tertiary)tert-叔，三级叔，三级quaternary季，四级季，四级n-p
38、entaneneopentaneisobutane正戊烷正戊烷新戊烷新戊烷异丁烷异丁烷Pentane2,2-dimethylpropane2-methylpropanetert-butanoliso-butanaminesec-butanamine叔丁醇叔丁醇异丁胺异丁胺仲丁胺仲丁胺2-methyl-2-propanol2-methylpropanamine1-methylpropanamine第二十六页，共81页。Theunivalentradicalderivedfromacyclicalkeneoralkynehastheendings“-enyl”or“-ynyl”,(alkeneal
39、kenyl)(alkynealkynyl),andthepositionofthedoubleortriplebondisindicatedwherenecessary.(unlikealkanealkyl)e.g.1-propenyl2-butenylethynyl2-propynyl第二十七页，共81页。Thefollowingnon-systematicnamesareretainedEthylene(乙烯）乙烯）Allene（丙二烯）（丙二烯）Acetylene（乙炔（乙炔(yqu)）Isoprene（异戊二烯）（异戊二烯）Vinyl（乙烯基）（乙烯基）Allyl（烯丙基）（烯丙基）I
40、sopropenyl（异丙烯基）（异丙烯基）第二十八页，共81页。NomenclatureofacyclichydrocarbonswithtwoormoredoubleortriplebondsvTwoormoredoublebonds:theendingwillbe“-adiene”,“-atriene”etc.(alkadiene)vTwoormoretriplebonds:theendingwillbe“-adiyne”,“-atriyne”etc.(alkadiyne)e.g.2-methyl-1,3-butadienepropadiene2,5-dimethyl-2,4,6-oct
41、atriene3-ethyl-4-methyl-1,6-heptadiyne第二十九页，共81页。Nomenclatureofmonocyclicaromatichydrocarbons苯苯甲苯甲苯二甲苯二甲苯苯乙烯苯乙烯异丙苯异丙苯均三甲苯均三甲苯benzenetoluenexylenestyrenecumenemesitylene苯基苯基(bnj)甲苯基甲苯基(bnj)二甲苯基二甲苯基(bnj)苯乙烯基苯乙烯基异异丙苯基丙苯基(bnj)均三甲苯基均三甲苯基(bnj)苄基苄基Phenyltolylxylylstyrylcumenylmesitylbenzyl第三十页，共81页。Commonn
42、amesretainedforthedisubstitutedbenzeneortho-,o-邻邻meta-,m-间间para-,p-对对m-methylbenzylm-tolyl3,4-dimethylphenyl3-methylbenzyl3-tolylo-styrylp-cumenyl3,5-dimethyl-4-ethylphenyl2-styryl4-cumenyl第三十一页，共81页。SomeimportantFamiliesoforganicmoleculesSaturatedhydrocarbons:suchas:Alkanes;cycloalkanes;Un-saturate
43、dhydrocarbons:suchas:alkenes;alkynes;cycloalkenes;cycloalkynes;cycloalkadienes;cycloalkadiynes;Aromaticcompouds:benzene;biphenyl;naphthaleneandotherfusedandpolycyclicaromatichydrocarbons;Compoundswithfunctionalgroups:alkylhalides（卤代烃）（卤代烃）;alcohols（醇）（醇）;phenols（酚）（酚）;ethers（醚）（醚）;amines（胺）（胺）;Compo
44、undswithfunctionalgroups:aldehydes（醛）（醛）;ketones（酮）（酮）;quinones（醌）（醌）;carboxylicacids（羧酸（羧酸(susun)）;esters（酯）（酯）;acylhalides（酰卤）（酰卤）;acidanhydrides（酸酐）（酸酐）amides（酰胺）（酰胺）;imides（亚胺）（亚胺）;第三十二页，共81页。Compoundswithfunctionalgroups:alkylhalides（卤代烃）（卤代烃）;alcohols（醇）（醇）;phenols（酚）（酚）;ethers（醚）（醚）;amines（胺）
45、（胺）etc.valkylhalidesR-Xhalogen(-halo)(-Cl,-Br,-F,-I)vAlcoholsR-OHhydroxygroup(-OH)vPhenolsAr-OH hydroxygroup(-OH)vEthersR-O-R Alkoxygroup(O-R)vAminesR-NH2aminogroup(NH2)第三十三页，共81页。Alkylhalides(haloalkaneoralkylhalide)Alkylhalidesareclassifiedasprimary,secondary,or tertiarydependingonthecarbontowhich
46、thehalogenisattached.第三十四页，共81页。Thecommonnamesofthealkylhalidesareobtainedbycitingthenameofthealkylgroupfollowedbythenameofthehalogen.(alkylhalide)IntheIUPACsystem,alkylhalidesarenamedassubstitutedalkanes.Thesubstitutedprefixnamesforthehalogensendin“o”(fluoro,chloro,bromo,iodo).(haloalkane)第三十五页，共81
47、页。AlcoholsThecommonnames,similartoalkylhalides,areobtainedbycitingthenameofthealkylgrouptowhichtheOHgroupisattached,followedbytheword“alcohol”.(alkylalcohol)TheIUPACnameforanalcoholisobtainedbyremovingthe“e”fromthenameofthealkaneandaddingthesuffix“ol”.(alkanol)Nomenclatureofalcohols第三十六页，共81页。Amines
48、arecompoundsinwhichoneormorehydrogenofammoniahavebeenreplacedbyalkylgroups.Thereareprimary,secondary,andtertiaryamines.Thisclassificationdependsonhowmanyalkylgroupsarebondedtothenitrogen.(!notcarbon)Nomenclatureofamines第三十七页，共81页。vThecommonnameofaamineisobtainedbycitingthenamesofthealkylgroupsbonded
49、tothenitrogeninalphabeticalorder.Theentirenameiswrittenasoneword.(alkylamine)e.g.第三十八页，共81页。vTherearetwoIUPACapprovedwaytonameanamine.1.Itcanbenamedasasubstitutedalkaneusingtheprefix“amino”todesignatetheaminesubstituent.(?aminoalkane)2.Italsocanbeennamedwithafunctionalgroupsuffix-“amine”.The“e”atthe
50、endofthealkanenameisreplacedby“amine”.ThenamesofsubstituentsbondedtothenitrogenareprecededbyanN(initalic)toindicatethatthesubstituentisbondedtoanitrogenratherthantoacarbon.(N-alkyl)alkanamine第三十九页，共81页。第四十页，共81页。vAmineswithfouralkylgroupsbondedtothenitrogen-andthereforeapositivechargeonthenitrogen-a